The 1990s was a great decade for country music. As the ’80s came to a close there were a few country singers that were rising stars. Alan Jackson, Clint Black, Lorrie Morgan, Garth Brooks and others were becoming superstars. As the ’90s began, these and other artists – along with the validation from SoundScan – made country music the biggest music genre in the US.
Along with the great country artists of the ’90s, the songs they sang made the decade memorable in the eyes of the fans. The lyrics were fun, sad, familiar, but now cliche, and understandable. The production of the songs was perfect. The instrumental hooks were filled with screaming fiddles, waning steel guitars, and even simple acoustic sounds.
It’s been over ten years now since one of the greatest decades in country music came to a close.
Let’s take a look at the songs that affected so many…
100) Queen of Memphis – Confederate Railroad
Confederate Railroad had a few big hits in the early ’90s. Arguably their best song was Queen of Memphis. The song is catchy and fun. The guys in the band put a great melody hook with a story of falling in love. The recipe was a success and the song climbed all the way to #2 on the charts – the biggest hit for the band. The guys are still going strong today and fans love hearing Queen of Memphis during every show.
99) Doctor Time – Rick Trevino
Rick Trevino brought a unique flavor to country music in the ’90s. His brand of country music was tinged with Tex-Mex influence. The songs he released were catchy and it led to a successful career for the young performer. One of his most successful songs was Doctor Time. The song climbed into the top five and helped his English debut album go gold. The hook is memorable and the song is still heard on country radio today.
98) Whatever Comes First – Sons of the Desert
The Sons of the Desert had an interesting run in country music. They’re first break came in ’96 when they sang the background vocals on Ty Herndon’s hit album Livin’ In a Moment. In ’97 the guys had their first and only country top ten hit with Whatever Comes First. The band later had success by singing background vocals on Herndon’s #1 hit It Must Be Love. The guys also received praise and recognition for singing background vocals on Lee Ann Womack’s signature song I Hope You Dance. The guys have since gone their separate ways, but their biggest hit remains a greatest song of the ’90s.
97) They’re Playin’ Our Song – Neal McCoy
Neal McCoy was always a dark horse in country music. It took him quite awhile to finally get a big hit on country radio. Once he broke out there was no stopping him. He racked up a bunch of top ten hits in the ’90s. A fan favorite was They’re Playin’ Our Song. The song was a big hit and one of McCoy’s most memorable. McCoy earned Entertainer of the Year recognition in ’98. He’s still entertaining fans all over the country and is a huge draw. He continues recording for various labels as well. And fans are still requesting his songs to be played on the radio today.
96) If The World Had a Front Porch – Tracy Lawrence
Tracy Lawrence was a major success in the ’90s. He consistently put songs and albums at the top of the charts. Of all the so called ‘Hat Acts’ to come out in the early ’90s, Tracy Lawrence was one to find tons of success. If The World Had a Front Porch was one of Lawrence’s best hits. The song is a great look at how down home roots play a major role in American culture. Millions connected with the message and melody in the song. If you listen to country radio today you’ll probably hear If The World Had a Front Porch every once in a while.
95) Whose Bed Have Your Boots Been Under – Shania Twain
The queen of country music in the ’90s was Shania Twain. Her two albums sold over 30 million albums in the US alone. A huge hit from her breakout album The Woman In Me was Whose Bed Have Your Boots Been Under. Shania knew how to sing a story that spoke to women and she knew how to craft a catchy hook. Even men would sing along to this song in their trucks – admit it, you did. It’s a classic song that is a huge part of the success Shania Twain has had in her career.
94) Little Good-Byes – SHeDaisy
In the late ’90s, country fans were lucky enough to hear the sister trio of SHeDaisy on the radio. The trio’s first big hit was Little Good-Byes. The girls sang the hell out of the song and women around the country took notice. The band became huge stars in the country music world. More hits followed and the girls have been releasing big hits ever since. Fans will always remember the song that made SHeDaisy stars. The song is still a favorite on radio today.
93) How Forever Feels – Kenny Chesney
By the late ’90s, Kenny Chesney was still working on a few big hits, but he hadn’t reached the superstar status he would go onto enjoy in the ’00s. In 1999, Chesney released How Forever Feels. Country fans got a little taste of what later came with Kenny’s love for the islands. The song had a slight Buffett feel and the video saw Kenny hanging out on the beach and in the ocean. How Forever Feels was Chesney’s biggest hit at the time. He’s since gone on to have much larger success, but fans first got a taste in ’99 with How Forever Feels.
92) Rockin’ Years – Dolly Parton and Ricky Van Shelton
By 1991, Ricky Van Shelton was a superstar in country music. He was on a roll of #1 hits and his albums were selling in the millions. In a few short years in the late ’80s, Shelton had taken the country music audience by storm. He was a distinctive sounding artist and fans were loving every song he released. In 1991, after a duet didn’t work out with George Jones, Dolly Parton got together with Shelton and they released Rockin’ Years. The song is a sweet love story told in a very clever way. The song is a country music classic. It came out in ’91, but the song could have been released in any decade. It’s a timeless country classic.
91) From Here To Eternity – Michael Peterson
It’s said that if you can get a song to become a classic event song you’ll have a hit for life. Whether it’s a classic sporting event song, a birthday song, an anniversary song or a wedding song, the saying seems to be true. In 1997, Michael Peterson released a classic wedding song with his #1 hit From Here To Eternity. The song was a huge hit for Peterson and became a regular at weddings in the late ’90s. The song is still a classic today. Peterson is still playing and releasing new music. He’s also writing for other artists. It seems that Peterson’s legacy will live with his timeless song. And that’s not so bad.
90) It Would Be You – Gary Allan
Gary Allan’s career really didn’t get going until the ’00s, but he still had a couple hits in the ’90s. Allan has a distinctive voice and he drew enough attention to have a top ten hit and one of the greatest songs of the ’90s with It Would Be You. Allan put his raspy and passionate vocal to the track that compares the love of his life and the heartbreak she caused with other recognizable things. The song was a hit with fans. Allan recently said that in his shows he’ll include the song when he’s touring with an artist that has an older fan base. Fans usually remember the hit and Allan seems to enjoy playing it for them.
89) Don’t Laugh At Me – Mark Wills
Mark Wills was just a kid when he started releasing hits in the mid-’90s. He covered some difficult material and brought it to the country masses with Don’t Laugh At Me. The song was about tolerance and acceptance. The song asks others to have a little respect and even a little care when it comes to the situations of others. The song was a major hit and had a few people thinking about the way they lived their life. It was a major breakthrough for Wills who at the age of 24 was still climbing his way to star status in the country world. He continues recording and touring today.
88) There’s Your Trouble – Dixie Chicks
It took nearly ten years, but in 1998 the Dixie Chicks changed things in country music. The group’s first #1 hit was There’s Your Trouble. The song kicked off a string of big hits for the Chicks. They went on to sell millions of records while touring the world and winning tons of awards. The song was unique when fans first heard it on the radio. The talented trio may have run into a bit of unwarranted controversy later in their career, but it’s hard to argue the quality of the songs they put out during their run at the top.
87) Bye, Bye – Jo Dee Messina
Jo Dee Messina’s career got off to a hot start in ’96 with her smash hit Heads Carolina, Tails California. You couldn’t go 45 minutes on country radio without hearing the song. A few less successful singles followed and many were thinking Messina would be a one hit country wonder. However, she covered the Phil Vassar-penned song Bye, Bye and in ’98 she had her breakthrough. The song was a #1 smash success and it paved the way for more huge hits from the feisty redhead.
86) Good As I Was To You – Lorrie Morgan
By the mid-90s, Lorrie Morgan had herself a huge career. She had a couple of #1 hits and plenty of top tens. Her albums were selling in the millions and she was coming off a successful Greatest Hits album. However, there was still room for a great song and in 1997 Morgan released Good As I Was To You. The song was a top five hit for Lorrie and it continued her reign as one of country’s greatest female stars.
85) All The Good Ones Are Gone – Pam Tillis
The daughter of a country legend, Pam Tillis had a huge career during the ’90s. By 1997 she was one of country’s biggest stars and certainly a huge female star. All The Good Ones Are Gone became a sad yet important song for women across the country. The song is sad and lonely, but part of what helps everyone get through each day is knowing there are others feeling the same way out there. The song was a major hit for Tillis and remains one of her biggest to date.
84) Ten Thousand Angels – Mindy McCready
Mindy McCready was young and fearless when she released her breakout album Ten Thousand Angels in 1996. The title song was a top ten smash for the girl with the true country voice. Other big hits followed and her album sold over two million copies. In subsequent years, McCready has struggled with her personal and professional life, but the big hits she had in the ’90s still stand as some of the best of the ’90s.
83) Dumas Walker – The Kentucky Headhunters
The Kentucky Headhunters were a true bar band that reached the heights of country music success. In 1990, the guys had their breakout hit with the appropriate ode to their favorite bar Dumas Walker. The song reached #15 on the charts, but its impact was felt throughout the ’90s. Each member of the band is credited with writing the song. Together they put together a simple yet favorite story with a great hook and sing along melody. It’s a true classic in country music.
82) The Fool – Lee Ann Womack
Lee Ann Womack is known as one of the traditional singers in country music. Her voice bleeds country down to her soul. The song she records speaks to the true fans of country music. Womack’s breakout hit was The Fool in 1997. The song climbed all the way to #2 that year and is still a favorite among the women in country music audiences. The song is a sad tale about how women find themselves in losing relationships. It’s a sad, but powerful song as it lets others know they’re not alone in their relationship struggles.
81) How Your Love Makes Me Feel – Diamond Rio
Diamond Rio had a huge career in the ’90s. The band reached the top of the charts with their debut single in 1991, but it wasn’t until six years and many other hits later that they reached the top again with How Your Love Makes Me Feel. It’s a crazy song about cows standing in the road and buying ice cream. The song is a classic. It’s fun to sing along with and everybody feels like dancing when it comes on the radio. A great hit from one the greatest decade in country music.
80) It’s Your Love – Tim McGraw and Faith Hill
Tim McGraw and Faith Hill were the biggest story in country music in the mid-’90s. The two toured together, fell in love, got married and had a family. It’s a fairy tale love story. At the beginning of the romance was the song It’s Your Love. Fans fell in love with the couple as they sang about how much they loved each other. The song was a major hit and raised the status of McGraw and Hill – already big stars. The two have continued recording the occasional duet, but none has quite reached the level of success of It’s Your Love. As a duo, it may be there signature song and it certainly was a big part of the ’90s in country music.
79) We Danced Anyway – Deana Carter
After the major success of her debut single Strawberry Wine, girl next door Deana Carter followed up with another smash hit We Danced Anyway. The song was about throwing caution to the wind when it comes to love. Fans loved the song and continued buying Carter’s debut album by the millions. Carter would continue her string of success with more hits from the album, but We Danced Anyway is still one that is played the most on country radio.
78) Nobody Knows – Kevin Sharp
Kevin Sharp took a popular R&B song and put a little country in it with Nobody Knows. The song was a big hit for Tony Rich and later became a big hit for Kevin Sharp. The song made Sharp a success. It kicked off a gold album for Sharp. He was able to follow it up with a few more hit singles. Nobody Knows is another great example of how good songs can be played to any music audience. As Willie Nelson says, “There are two kinds of music – good and bad.” Nobody Knows falls into the ‘good’ category.
77) Buy Me A Rose – Kenny Rogers
Kenny Rogers’ career has been up and down for over 40 years now. During his biggest run in the late ’70s and early ’80s Kenny was selling more records than anyone in music. His Greatest Hits album sold in excess of 12 million copies in the US alone. However, by the end of the ’90s there was little attention paid to Kenny. In October of 1999, however, Rogers self-released the song Buy Me A Rose. The song reached number one the following spring (we included it it here due to the release date and because it was climbing the charts in ’99). Kenny was back on top of the charts and making fans love the music he was making.
76) Too Much Fun – Darlye Singletary
There were a lot of fun songs in the ’90s and Daryle Singletary’s 1995 hit Too Much Fun was aptly named. The song was a top five hit that year and established Singletary as a rising star. Singletary had the voice of a country traditionalist. He had a few top five hits over his career and Too Much Fun became his signature song. It’s still played on radio today when fans need a little excuse to go a little overboard every now and then.
75) Sold (The Grundy County Auction Incident) – John Michael Montgomery
John Michael Montgomery had fans gasping for air as they tried to keep up with the rip-roaring hit song Sold. In 1995, JMM was on top of the country world. He could have been just another hat act with three names in the mid-’90s, but he churned out hits at a rapid pace and sold millions of records. Sold is still a fan favorite today. JMM is still able to keep fans on their toes with the ultra-fast chorus as he sings about picking up a woman at the local county auction.
74) You’re Easy on the Eyes – Terri Clark
Canadian country singer Terri Clark had herself a ton of success in the ’90s. She racked up multiple number one hits, a few awards, and millions of albums sold. In 1998 she had one of her biggest hits with You’re Easy On The Eyes. The song shot all the way up to #1 on the charts. Terri’s success continued in the US for a few more years. Today she’s still recording and touring and finding big success in her home country.
73) What Kind of Fool Do You Think I Am – Lee Roy Parnell
Lee Roy Parnell was trying to have success in the early ’90s with a few unsuccessful singles. Parnell found his success in 1992 with the hit single What Kind of Fool Do You Think I Am. The song climbed all the way to #2 on the charts. Parnell followed the success with more hit singles over the next few years. His style was unique at the time. He played slide guitar better than anyone and had a voice that was distinctive on radio. His best songs are still heard on radio today. Perhaps the most popular is What Kind of Fool Do You Think I Am.
72) One Way Ticket (Because I Can) – LeAnn Rimes
LeAnn Rimes was a major success in the ’90s. Her debut album sold millions of copies on the success of the first single Blue. Her first number one hit came later as her third single One Way Ticket (Because I Can). The song was a huge hit on country radio. Rimes has gone on to have success in both pop and country music. Still young and in her twenties, Rimes seems to be driven to continue having success in country music.
71) Guys Do It All The Time – Mindy McCready
Mindy McCready had her first and only #1 hit with Guys Do It All The Time. Her second single off her multi-platinum album Ten Thousand Angels became her signature song. Guys Do It All The Time became an anthem for women in the mid-90s. The song is about ladies going out and having a good time using the excuse that…
70) Wild Angels – Martina McBride
Martina was coming into her own as a rising country star in the mid-90s. In 1995-96 she had her first number one hit with Wild Angels. The song featured Martina’s soaring vocals. Women and girls were singing along at the top of their lungs. It’s one of Martina’s best songs in a collection that features many fan favorites. The song is still popular on country radio and during Martina’s concerts today.
69) Running Out of Reasons to Run – Rick Trevino
Rick Trevino is back on the countdown with his biggest hit Running Out of Reasons To Run. The song climbed all the way to #1 and remains Trevino’s only top country hit to date. The single came off Rick’s hit album Learning As You Go. The song was a big hit and you can still hear it on radio today. It’s a classic sing along song that is a favorite of many country music fans.
68) That Ain’t My Truck – Rhett Akins
As far as success on the charts, That Ain’t My Truck wasn’t Rhett Akins biggest hit, but in terms of lasting effect, it certainly is Rhett’s signature song. The song tells the tale of a guy that drives past his girlfriend’s house only to notice that another guy’s truck is parked in the driveway. He realizes that the girl he loves is probably not interested as much in their future as he is. It’s a sad song, but one fans could relate to. The song is extremely catchy and sometimes that’s what it takes for a song to have the longevity of That Ain’t My Truck.
67) Goodbye Says It All – Blackhawk
People often to think about Blackhawk when they think about the best bands in the history of country music, but perhaps they should. The trio had a huge run of success in the ’90s. They racked up hit after hit. The collection of songs they cut and released weren’t just hits, they became timeless classics that are still favorites of many today. Goodbye Says It All was a huge hit for the guys. It’s still a favorite today. Guitarist Van Stephenson died in 2001 of complications with skin cancer. The other two guys still tour and record today. Their impact is still felt with hits like Goodbye Says It All.
66) Livin’ On Love – Alan Jackson
Besides Garth Brooks, it’s hard to find any country artist that had more success in the ’90s than Alan Jackson. It seemed like Jackson was consistently in the top five on the country charts for about 8-10 years during the great decade. Jackson sang songs about love and life as a guy from a small town in the southern US. Fans loved Jackson’s easy going nature and his smooth delivery. Livin’ On Love was a story about Jackson’s parents. The song was full of great melodies and lyrics most fans could connect with. When people don’t have much their only choice is to live with the love of each other.
65) Cafe On The Corner – Sawyer Brown
Sawyer Brown found a lot of success during the ’80s after their win on the popular talent show Star Search. The guys entered the second phase of their career in the ’90s with more big hits. In 1992, they released Cafe On The Corner. The song is about the struggling nature some folks run into with work during their later careers. The song is timely given today’s happenings in the economy. it’s a fan favorite hit. The guys are still a major tour draw each season and lead singer Mark Miller races from end to end of the stage singing their many hits.
64) Pickup Man – Joe Diffie
Joe Diffie was a major success in the early and mid-90s. He is now known most for his tongue-in-cheek songs. He racked up major hits and could easily have more than one signature song, but his 1994 #1 smash hit Pickup Man is perhaps his most well-known song. The double meaning song became an anthem for all the guys in the crowd that love their trucks. It’s a fun song and still gets requested on a consistent basis today. Diffie is still recording and touring today. He hasn’t had a hit in America for a few years, but never count this talented Oklahoman out.
63) Callin’ On Baton Rouge – Garth Brooks
It’s fairly obvious that the biggest success in country music in the ’90s was Garth Brooks. He has sold more records than any artist in any genre except for The Beatles, Michael Jackson and perhaps Elvis. Garth single-handedly lifted every artist in his wake as he charted albums simultaneously at the top of the Billboard 200. Ask Garth Brooks what the reason for his success was and he’d probably tell you that it was a result of the songs he was fortunate to record. A huge hit for Garth was Callin’ Baton Rouge. the song was written by the great country songwriter Dennis Linde. Callin’ Baton Rouge is one of the most played Garth Brooks songs on the radio still today.
62) State of Mind – Clint Black
By 1994, Clint Black was a huge star in country music. He had broken out as the initial leader of the Class of ’89. Garth Brooks later overtook everybody from that class, but Black’s success continued. In ’94 he released State of Mind. The song was a #2 hit on the charts and became a signature hit for Black. He said he had written the song quite some time before its release. The song is unique. Black always brought a lot of harmonica to his records and State of Mind features a great intro with Black playing the harmonica. It’s a classic song from one of the best artists in country music.
61) He Thinks He’ll Keep Her – Mary Chapin Carpenter
Mary Chapin Carpenter’s 1992 album Come On Come On was a major success. The album spawned six hit singles and sold over 4 million copies. The 5th single from the album was the #2 hit He Thinks He’ll Keep Her. Mary Chapin Carpenter has always been known for her clever and smart lyrics about the beauty and power of women. This song was no different. The song was crafted with a great melody and is one of Mary’s signature songs. It’s an anthem for great women everywhere.
60) Hard Workin’ Man – Brooks & Dunn
In 1991, Brooks & Dunn emerged on the country music scene and changed the way fans perceived the genre. Kix Brooks and Ronnie Dunn were struggling solo acts, but together they were a huge success. After their debut album sold over six million copies and made them overnight superstars, the guys released their sophomore set. The lead off and title single was Hard Workin’ Man. The song is an ode to the hard working folks in the US. Nobody could have done this song better than Kix and Ronnie. Kix rocked the track with his energy and Ronnie added his one-of-a-kind vocals. Now on their last rodeo tour, the guys will soon separate. Their legend is forever stamped on country music.
59) She Don’t Know She’s Beautiful – Sammy Kershaw
Starting in 1990 and running for about 8-10 years, Sammy Kershaw had a great run as a country star. His biggest hit and currently only #1 hit was She Don’t Know She’s Beautiful. The song is for all the women out there that don’t know it, as Sammy puts it. Many of the great women out there don’t realize that men simply love the way they look when they don’t realize it. The song has a great melody and is still extremely popular on country radio. Sammy still tours with his band each year and She Don’t Know She’s Beautiful is still one of the most popular in the set.
58) Life’s a Dance – John Michael Montgomery
As 1993 kicked off in the US, a young, energetic guy with the biggest dimples you’ve ever seen emerged on the country music scene with an infectious debut single. Life’s a Dance became the first of many big hits for John Michael Montgomery. The song became a signature hit for JMM and that’s impressive given the number of quality hits he had over his career. Some say the song is an obvious rip off of Garth Brooks’ The Dance, but in reality Life’s a Dance does just fine on its own. The song is incredibly catchy and is requested on radio stations all over the US today. It’s a great example of why country music was great in the ’90s.
57) Small Town Saturday Night – Hal Ketchum
In 1991, the major label debut single from singer Hal Ketchum – Small Town Saturday Night – was released. The song climbed all the way to #2 on the charts and has never left country radio playlists. The song tells the common story of what people do in small towns all across the US. Millions connect with the song and sing along with the catchy chorus when it plays over the speakers. It’s still an anthem for many that look for a little fun on Saturday night.
56) I Saw The Light – Wynonna
In 1992, The Judds took a break from recording and touring. Naomi needed time to rest and recover and pursue other interests. Daughter Wynonna signed a solo deal and began her career on her own. Wynonna the solo artist turned out to be a huge success. Wynonna’s second single as a solo act was I Saw The Light. The song is uptempo and catchy. It was popular in 1992 and remains popular today. Wynonna is still releasing new music and touring. Word is she will reunite with her Mother to record new music and tour in 2010.
55) Independence Day – Martina McBride
It’s unusual for a song that missed the top ten on the charts to become a signature song for a superstar artist. That is the case, however, for Martina McBride. The song Independence Day is about domestic abuse and how it affects an entire family including a daughter. The song is not a comfortable topic, but it connected with many. Martina left her mark on the song with soaring chorus notes and passionate vocals. Independence Day is still a popular song today.
54) Fancy – Reba McEntire
Of all the Reba songs that could make this list, it’s surprising – on the surface – that the #8 hit from 1991 Fancy had the most impact. The story of prostitution with Reba’s rendition became a popular hit throughout the decade and still one of Reba’s best known songs. Reba’s sassy vocal and catchy delivery had girls singing along to the distaste of many parents. The impact was positive, however, and Reba is an inspiration for a generation of female country stars.
53) Love, Me – Collin Raye
Collin Raye had an almost quietly successful career in throughout the ’90s. He churned out multiple big hits that still play well today. Perhaps his best song is his first big hit Love, Me. The song is about true love as told by a grandson. The still has the ability to bring tears to the eyes of fans as they reflect on their own experiences with lifelong loves. Collin Raye had major label success the turn of the ’00s, but he’s still actively recording and touring.
52) John Deere Green – Joe Diffie
Mr. Tongue-In-Cheek Joe Diffie was releasing quality fun songs long before Brad Paisley and Jason Aldean came onto the country music scene. Diffie had a knack for writing and finding songs that were fun and touching at the same time. His 1993 top five smash hit John Deere Green was the best of the bunch. The song tells the tale of a young couple in love. To celebrate their love, Billy Bob writes Billy Bob Loves Charlene in big John Deere Green letters on the local town water tower. It’s a great tune that fans still love singing along with today.
51) Longneck Bottle – Garth Brooks and Steve Wariner
By the end of 1997, Garth Brooks was at odds with his record label. Brooks was upset about the lack of sales (by his standards) of his album Fresh Horses. He wanted to make sure his next album was a major hit. The first single released from the album Sevens was Longneck Bottle. The song, a duet with Steve Wariner, became a major #1 smash hit. More hits followed and Sevens sold extremely well. Longneck Bottle marked a bit of a comeback for Brooks and a big comeback for Wariner.
50) If I Know Me – George Strait
George Strait had so many hits in the ’90s it’s hard to pick for this list. If I Know Me is a song that still sees a lot of play on radio and seems to be a fan favorite. The song was a #1 hit for Strait in 1991. The song tells the story of a guy that recently broke up with a girlfriend. He’s questioning his decision and playing with the idea that maybe he can’t really go through with it. It’s a common personal fight men tend to go through. Perhaps that’s why it was and remains so popular. That and nobody sings a song like King George.
49) Down Home – Alabama
Alabama ruled the 1980s in country music. They were still releasing hits as the ’90s came and Down Home was a major hit for the group. The song is classic Alabama. The story of growing up in rural America. The good times, the bad times, and all the fond memories. As usual, Alabama crafted a catchy song that fans loved to sing along with. It’s what made them so special to country music.
48) Vidalia – Sammy Kershaw
It’s hard to believe that a song about a girl named after an onion could become such a fan favorite hit. The song was Sammy Kershaw’s Vidalia cracked the top ten in ’96 and became a signature song for Kershaw. According to him, it’s still a fan favorite in concert and transcends generations. The song is a sing along favorite for country fans of all ages. It wasn’t Sammy’s biggest hit during his successful run in the ’90s, but it’s a fun song that has become a timeless big hit.
47) Walk On Faith – Mike Reid
In late 1990 and 1991, former Cincinnati Bengals Defensive end Mike Reid took his debut single to #1 on the country charts. Walk On Faith had an infectious guitar riff and optimistic lyrics. Reid had been writing songs for successful artist since his retirement from football in 1974 and he’d had some big success. He continues writing songs for other artists today, but he might still best be known the most for Walk On Faith when it comes to his recognition in the music industry.
46) Seminole Wind – John Anderson
By the time the ’90s came around, John Anderson was experiencing a slump. He had major success in the early eighties, but things changed toward the end of the decade. That all changed in 1992 when John released his double platinum album Seminole Wind. The album produced a string of hits. The title track from the album went all the way to #2 on the charts. The song seemed to be too regional for national success on the surface, but fans all over the country connected with the story about Seminole Indians. Fans loved the melody and still request the song often.
45) You Don’t Even Know Who I Am – Patty Loveless
During the mid ’90s, Patty Loveless was the biggest female in country music. She was winning awards and her songs were having a major impact on the charts. In 1995, she released You Don’t Even Know Who I Am from her Album of the Year When Fallen Angels Fly. The song became a top five hit on radio and connected with country fans. The song is about a dying relationship. It doesn’t put blame on either person involved. According to Patty, the song lets people know they’re not the only ones experiencing the sad and lonely situation of an ending relationship. Patty put vocals on the track like only she can. The song is still a favorite today.
44) Sittin’ On Go – Bryan White
In the mid-90s, Bryan White was just about as hot as an artist could be in country music. He was only in his early twenties at the time, but had the charm and maturity of a guy much older. His voice was unique and his talent was undeniable. In 1997, he released the 4th and final single – Sittin’ On Go – from his platinum album Between Now and Forever. The song went all the way to #1. The song was uptempo and catchy. Fans still sing along each time it comes on the radio. Bryan took a few years off during the ’00s to raise a family. Now that his sons are a little older he is back out recording and touring again.
43) Goin’ Through The Big D – Mark Chesnutt
Mark Chesnutt had a lion’s share of hits in the ’90s. A traditional sounding guy from Texas, Chesnutt drew on the influence of the great George Jones. He took the fun Goin’ Through The Big D all the way to #2 in ’94-’95. The song took an upbeat mood to the common situation of divorce. The song perfectly written as it walked a fine line of cliche and commonalities. The song remains a fresh perspective on the all too common divorce so many experience.
42) Every Once in a While – Blackhawk
Looking back now, Blackhawk was an amazing band. The songs they recorded and released during the ’90s are some of the best country songs every created. Every Once And A While was the 2nd single off the band’s debut album. The song reached #2 on the charts in 1994. The story of two lovers that still think about each other every now and then with the killer melodies the band created, the song is still a favorite of country fans today.
41) Go Rest High On That Mountain – Vince Gill
In 1995, Vince Gill released the tear-jerking song Go Rest High On That Mountain. The song won Song of the Year at the CMA Awards as well as two Grammy awards. The song began as a tribute to Keith Whitley, but Gill finished the song after the passing of his brother. The song has helped many grieve the loss of loved ones over the years and remains one of Gill’s biggest hits despite only reaching #14 on the charts.
40) Old Enough To Know Better – Wade Hayes
The early and mid-’90s saw an influx of popular guy performers. Aft the success of Alan Jackson, Garth Brooks, George Strait, and Clint Black, Nashville execs were looking for any guy with a Southern twang a hat. In 1995, Wade Hayes had his turn as a big country act. Old Enough To Know Better was an instant hit with fans. Everybody has a little kid in them. And we all tend to make a mistake or two that make others shake their head and say that we’re…
39) I Don’t Call Him Daddy – Doug Supernaw
As 1994 kicked off in country music, Doug Supernaw was a rising star. He was on the (at the time) independent BNA Records label. His 2nd single Reno had just climbed into the top five on the charts and he was becoming well known across the US. As 1994 began, Doug’s third single I Don’t Call Him Daddy made him a legitimate star. The song was about a divorced family as told by a young boy. The song had been a minor hit for Kenny Rogers years earlier, but the song belongs to Supernaw. In years since his stardom Doug has slipped into a real life Crazy Heart story… With Father’s Day coming next weekend you’ll be sure to hear this song on the radio.
38) Cadillac Style – Sammy Kershaw
Sammy Kershaw debuted in 1991 with his debut hit single Cadillac Style. Kershaw instantly drew comparisons to the great George Jones. The southern voice soaked in years of booze, hard work, and soul made Kershaw a hit with fans. Cadillac Style was catchy and fun to sing along to and fans ate it up. Kershaw built a solid career throughout the ’90s and never felt bad about the comparisons to the great George Jones.
37) When She Cries – Restless Heart
In 1992, ’80s country supergroup Restless Heart had an unlikely hit with When She Cries. The song became a hit on the country and pop charts and remains a classic on both charts to this day. The song marked the first time the band was without its lead singer. It’s usually difficult for bands to overcome the loss of a distinguishing part success, but Restless Heart had what is their biggest hit. The melodies were still there and the song still sounds great today.
36) My Love – Little Texas
Little Texas had become one of the biggest acts in country music by the time they released the third single from their double platinum album Big Time. The song was My Love and it would go on to become to the band’s biggest, first and only number one hit on the charts. Little Texas was known as the rock band of country music. The had rocking songs that fans loved, but like many hair metal bands of the late ’80s, Little Texas is most known for their big hit power ballad.
35) Why Didn’t I Think Of That – Doug Stone
It was the fourth and final single from his 1992 smash hit album From the Heart, but for Doug Stone Why Didn’t I Think of That has become his signature song. The tune is about a guy that loses the love of his life. He’s left contemplating the reasons he lost her. He sees all the things that her new love does and he wonders why he couldn’t do those simple things to make her stay. The song remains a favorite on country radio due to its catchy melodies and recognizable story. For Stone, the song remains a favorite at shows. Even though his career as slowed down and he’s had some legal issues, Stone continues recording and touring for the love of the music.
34) Choices – George Jones
In 1999, the greatest country music singer released a new album and a new single. Choices was the song and it became a top 30 hit for Jones. It wasn’t his biggest hit on the charts, but that didn’t take away from the impact the song had on audiences. Men everywhere connected with the song about life’s choices and how our decisions impact who we are and what we’ve done. The song is also remembered for the surprise Alan Jackson performance at the CMA Awards. Jones was asked to sing a shortened version of the song on the award show. He felt insulted and refused. So Alan Jackson cut off his own performance of Pop A Top and sang Choices in respect for his good friend and inspiration.
33) Time Marches On – Tracy Lawrence
Tracy Lawrence released his double platinum smash hit album Time Marches On in 1996. The title track made it all the way to number one as the second single off the record. The song has a unique beat that tells the story of a family over the course of many years. Fans loved the way Lawrence delivered the story. The song still stands out today as unique. Tracy Lawrence could deliver a song in the vein of traditional country artists from the 50s, 60s, and 70s. Time Marches On is one of Tracy’s biggest hits and still a favorite today.
32) What Mattered Most – Ty Herndon
Ty Herndon said he arrived in Nashville to record his first music with producer Doug Johnson. The first song they discussed was What Mattered Most. The two debated about the song thinking it may have too many words to become a hit. Together they finally decided that was the unique feature of the song that would make it stand out to listeners. The two were right and the song quickly climbed to the top of the charts in 1995. Herndon would have a few more hits before falling into some hard times later in his career. He’s back now recording and touring and seems to be very happy with his life.
31) Maybe It Was Memphis – Pam Tillis
If there is a signature song for the great Pam Tillis it has to be the passionate Maybe It Was Memphis. The song became a top five smash hit in 1992 for Tillis. In the ’90s and still today, fans of all ages know just about every word of the song. It’s great to be sitting in a car with someone when the song comes over the radio because both of you will usually belt out the chorus with as much passion as Tillis put on the hit track. Tillis originally cut the song in the ’80s, but nothing transpired until she re-cut the song for her 1991 breakout album Put Yourself In My Place.
30) She’s In Love With The Boy – Trisha Yearwood
Trisha Yearwood was a female country music sensation in the ’90s. She sold millions of albums and had tons of hits. Her voice was powerful and emotional. In 1991, Yearwood released her debut single She’s In Love With The Boy. The song tells the story of a young couple in love. The father of the girl in the song is a little angry with the boy because he’s a little rough around the edges. The girl’s mother then has to remind her husband that he was the same way when they started dating. The song made Yearwood a star. Her talent, dedication, and collection of songs made her a legend.
29) This Kiss – Faith Hill
Faith Hill was already a country superstar by the time her third album Faith was released in 1998. The lead off single from the album was This Kiss. The song turned Faith into a crossover sensation. The song is simple. It’s about young love and the great feeling of falling and being in love. At the time, Faith and husband Tim McGraw were the biggest acts in country music. Faith’s career equaled McGraw’s at the time and This Kiss stands as one of the greatest songs of the ’90s.
28) What’s It To You – Clay Walker
Texas country music sensation Clay Walker has been a star in country music since his 1993 debut album came out. The first single for Walker was the ultra-catchy and fun What’s It To You. The song is still popular with fans on radio. It’s impossible to avoid singing along to the lyrics when you hear this tune even today. These days, Walker is releasing a brand new album and riding high on the top five success of a new single. He’s battled with MS and changing country music tastes over the 17+ years he’s been a star, but somehow he still one of the biggest draws in country.
27) Gone Country – Alan Jackson
In 1994, Alan Jackson released a single that poked fun at the music industry as a whole. Since the emergence of artists like Garth Brooks, Shania Twain, and Jackson himself, there had been a rush for musicians to country music that may have been considered artists from other genres. Country had proven to be the biggest selling music genre and everybody wanted a piece of the pie. Gone Country was a catchy song that played on this phenomenon. Jackson was the perfect choice to sing. It was one of the few big hits he didn’t write or co-write for himself, but Gone Country is an Alan Jackson classic at any rate.
26) Blue Clear Sky – George Strait
George Strait had a ton of hits in the ’90s. It’s hard to pick a few for this list, but Blue Clear Sky has to be included. It’s a classic Strait song about love and the good things in life that surprise us. When the song was pitched to Strait he thought the lyrics should be changed to the more common phrase Clear Blue Sky. The songwriters and Strait’s producer let him know that the song needed to be Blue Clear Sky because that’s what Tom Hanks’ character Forrest Gump had said in the popular movie of the same name. George conceded and the rest is history.
25) Dust On The Bottle – David Lee Murphy
David Lee Murphy could have been just another hat act with three names, but in 1995 he released one of the most popular country songs of all time with Dust On The Bottle. The unique story of a young guy grabbing an old bottle of wine from a friend to take on a date became an instant hit with fans. The song has a rocking beat and a sing along chorus. Generations of fans still crank up the volume when it comes on the radio. Today, David Lee has become a major success as a songwriter for other artists. Most recently he wrote the smash hit Big Green Tractor for Jason Aldean.
24) Meet In The Middle – Diamond Rio
There were a ton of catchy, sing along songs in the ’90s, but Diamond’s Rio’s 1991 debut #1 hit Meet In The Middle may be the most catchy, most sing along, fun song ever. The opening guitar riff is awesome. The lyrics tell the story of two young lovers walking to meet each other halfway between each others house. The song is about the power of compromise in relationships, but the most memorable thing about the song will always be the sing along chorus.
23) Don’t Let Our Love Start Slippin’ Away – Vince Gill
It took a few years in the ’80s, but Vince Gill became a superstar in the ’90s. He won tons of awards. He put out a string of hit singles and he sold millions of albums. In 1993, the second single off his most successful album I Still Believe In You was released. The catchy Don’t Let Our Love Start Slippin’ Away became a #1 hit for Gill. It’s one of his most recognized songs today and still gets played often on the radio. Fans love the upbeat vibe of the song and the chorus is easy to sing along to.
22) Wild One – Faith Hill
Faith Hill became an instant success after her debut single Wild One climbed all the way to #1 in 1993. The song is one of Faith’s most well-known hits today. Like most great songs from the ’90s, Wild One is extremely catchy and fun. The song is about a young girl growing up with an adventurous nature. 17 years later, the song is still connecting with young girls that share the same spirit of the girl in the song.
21) I Like It, I Love It – Tim McGraw
Tim McGraw’s career got off to a slow start when his first three singles and debut album failed to make much noise. His career took off like a shot with his second album though. For the lead off single to his third album All I Want, Tim released I Like It, I Love It. The song became a classic Tim McGraw song. It was one of the best and most played songs of the ’90s and remains a McGraw classic. The song even has a dance remix for line dancers.
20) Chattahoochee – Alan Jackson
Alan Jackson was already having tons of success with his first three albums when he released the single Chattahoochee from his third album A Lot About Livin’ (And A Little ‘Bout Love). The song became a smash summer hit as well as becoming a signature song for Jackson. The song tells the story about growing up and hanging out with friends during the summer. The video featured Jackson slalom water skiing in his trademark ripped jeans. The sound and style of Chattahoochee influenced songs that followed in the ’90s.
19) Some Girls Do – Sawyer Brown
In the early 1990s, Sawyer Brown entered a new level of success in country music. Their second single off their hit album The Dirt Road was the SB signature song Some Girls Do. The song was written by lead singer Mark Miller. The tune is about how some girls turn the other when it comes to the hard working, good timing, fun loving, good old boys, but there is no reason to worry because when it comes to loving country boys – some girls do. It’s a classic song and usually the closer for every Sawyer Brown show. The guys are still releasing music and touring. If you haven’t seen them live yet you need to do it asap. They’re great.
18) Don’t Take The Girl – Tim McGraw
If Tim McGraw’s first hit single Indian Outlaw gained him enough notoriety to get noticed, his second hit single and first #1 Don’t Take the Girl made him a legitimate country star. Don’t Take the Girl had fans singing along for most of the ’90s and still today. While the song that made Jimmy Johnson and Tommy Thompson a little more famous in the country world, it really took Tim McGraw’s career to a new level of success and propelled him to the superstar he is today.
17) Any Man of Mine – Shania Twain
In the mid-’90s there was no one better at crafting an infectiously fun melody than Shania Twain. Any Man of Mine came out in ’95 and became Shania’s first American #1 hit. The song even had crossover success, reaching #31 on the pop charts. Everybody and that means everybody was singing the tune. Kids, adults, women, and men were all singing all to perhaps the catchiest song of the ’90s.
16) A Broken Wing – Martina McBride
If you watch American Idol or any singing competition, you’re sure to hear a cover of Martina McBride’s classic hit A Broken Wing. The song is a favorite of females of all ages. The song is about a female character escaping a difficult and abusive relationship. Martina nailed the vocals as she always does and very few compare to the original version despite the number of times it’s been covered.
15) Next To You, Next To Me – Shenandoah
With a distinctive lead vocalist and an upbeat melody, country band Shenandoah had their biggest hit in 1990. Next To You, Next To Me was a fun song to sing along to throughout the decade and remains a favorite today. It’s a simple song, but sometimes those are the most memorable.
14) Five Minutes – Lorrie Morgan
Lorrie Morgan is sassy, sexy, and one of country’s greatest female performers. To kick off the ’90s she released her best song Five Minutes. The song is about a woman, sick of man that isn’t giving enough in a relationship, leaving. She gives the guy five minutes to try and figure out his deal before she hits the road. The song became an anthem for women.
13) Brand New Man – Brooks & Dunn
As solo acts, Kix Brooks and Ronnie Dunn couldn’t get their careers started. In 1991, they teamed up and released their first single Brand New Man. The result was a new breed of country music. The song was rocking, in your face, boot stomping country music that made you take notice. With Ronnie’s soaring vocals and Kix’s contagious enthusiasm, Brooks & Dunn dominated the ’90s and changed things in country music.
12) Heads Carolina, Tails California – Jo Dee Messina
If you listened to country radio in 1996 you couldn’t go 10 minutes without hearing Jo Dee Messina’s debut hit single Head Carolina, Tails California. The song was a #2 smash hit that year and it made Jo Dee a star. The catchy melody spun the tale of two lovers looking for something to do. The answer? Flip a coin. It was a fun song and one of the best songs in a decade that saw many fun songs.
11) The Dance – Garth Brooks
Over the summer of 1990, a slow, simple song from newcomer Garth Brooks was released. The Dance was an unusual choice as a single to kick off the summer. Normally it’s the hard rocking, up tempo songs that are released in an effort to become summer anthems. But The Dance was special. The simple lyric about life and taking chances became a signature song for the mega-star Brooks as fans everywhere connected with the performance. Garth lobbied his label to release the song when they wanted to move on to the next album. Brooks convinced them and he says it’s the song that really jump started his career.
10) You’re Still The One – Shania Twain
Shania Twain’s now 20+ million selling album Come On Over started out selling records relatively slow. That was until the album’s third single was released in 1998. You’re Still The One was a song about her then husband, producer Mutt Lange. The song became an anthem for all those in love. Fans loved the song and loved Shania. The song became a smash hit on the country and pop charts and took Shania to a new level of mega-star success. To date, it’s her biggest hit and still receives big play on multiple radio formats.
9) Check Yes or No – George Strait
In 1995, George Strait was preparing to release a collection of every hit he had up to that point. Strait Out Of The Box was a huge collection of great country songs and is one of George’s best selling albums. To promote the album, Strait needed a new song to hit the charts. The single he choose was the smash hit Check Yes Or No. The song told the cute story of two young lovers falling in love forever with it all beginning with a passing of a note in grade school class. The note was sent from the little girl to the little boy and the question became the timeless chorus of the song. Check Yes Or No is still a favorite of many fans today and George is still racking up #1 hits and he doesn’t appear to be slowing down.
8) Wide Open Spaces – Dixie Chicks
In the second half of 1998, the Dixie Chicks released the title track from their breakout album Wide Open Spaces. The single became an anthem for girls all over the country. The song was about a young girl looking to get away and head out into the wide open spaces life had to offer. The song turned the Chicks into stars and helped the album sell over 12 million copies. The chicks gained some misguided criticism for a comment in 2003, but their legend survives today. They’re ultra-talented musicians and still producing some of the best country music today. Wide Open Spaces is a classic country song and I’m sure a few Dads still use it to remind their girls to check the oil.
7) Strawberry Wine – Deana Carter
It was an unlikely hit, but in the second half of 1996, Deana Carter saw her debut single Strawberry Wine go all the way to #1 on the country charts. The song was a waltz and had a slow, but melodic feel to it. Carter’s vocals fit perfectly as she sang about a young girl’s first experience with love on her grandparent’s farm one summer. Women and girls connected with the familiar story and the song would go on to win Song of the Year at the CMAs.
6) Amazed – Lonestar
After two successful albums, Lonestar parted ways with bass player John Rich (Big & Rich) and set out to release their third album. The result was Lonely Grill and in the summer of 1999 the second single from the album would take the band into surperstardom. Amazed was the song. Fans loved the song. It had a slightly more pop and adult contemporary sound that what Lonestar had previously released. The song spent 8 weeks at #1 on the country charts and reached #1 on the pop charts as well. The song was everywhere that summer and Lonestar would often have to play it twice at their concerts.
5) Should’ve Been a Cowboy – Toby Keith
The most-played song on country radio in the ’90s was Toby Keith’s debut single Shouldn’t Been A Cowboy. The song turned Keith into a new country star. The song was about a guy looking back and wondering what his life would have been like if he had followed the path of his cowboy heroes. At the time of the songs release – 1993 – many adult men from the baby boomer generation had grown up with classic western movies and TV shows. The song was their anthem and still is today as they reflect on their lives. It wasn’t a bad debut single for Keith even though he was told earlier by a Nashville executive that the song was no good.
4) I’m In A Hurry (And Don’t Know Why) – Alabama
In 1992, after being named artist of the decade, Alabama still had plenty of great music left. They released the single I’m In A Hurry (And Don’t Know Why) and the song became one of their biggest hits. The catchy chorus caught on immediately with listeners of all ages. In a decade that saw the expansion of computers and the Internet, it seemed like everybody was in a hurry to get something done. Alabama provided a catchy theme song for all of the busy listeners in country music. It’s a great song. The opening chorus with lead singer Randy Owen belting out the vocals is amazing.
3) Don’t Rock The Jukebox – Alan Jackson
For one of the biggest artists of the ’90s, Alan Jackson released his signature hit in 1991 with Don’t Rock The Jukebox. The story of the Don’t Rock The Jukebox was simple and told best by the man himself in the video – Don’t Rock The Jukebox. Jackson and his band were at a small town lounge. Jackson went over by the jukebox to talk to a band mate. One of the legs was broken and when Jackson leaned up against it his bass player said…
2) My Maria – Brooks & Dunn
Brooks & Dunn were one of the biggest acts in the ’90s. Their fans loved everything they put out, but in 1996 the duo released what has become their most well-known and most requested song. The cover version of the song My Maria became a sensation in the ’90s. The song was everywhere. People were even naming their kids Maria. Ronnie’s soaring vocals during the chorus and the music arrangement clicked with listeners. Fans requested B&D to sing the tune for their going away special in 2010. It’s one of the greatest country songs ever and definitely a top song of the ’90s.
1) Friends In Low Places – Garth Brooks
In 1991, the biggest star in country music history, Garth Brooks, released his biggest hit song. Friends In Low Places set Garth’s career on a whirlwind ride to levels of success unseen in country music. The song is a story about a guy letting an ex-girlfriend know that he doesn’t need her anymore and that he has the best friends a guy can ask for. The song has become a barroom anthem and is likely the most played song at country karaoke bars all over the US. For added effect, Garth added a third verse to the song. He sang it almost exclusively in his live shows and often had the fans sing the entire verse. It was a powerful idea and a reason Garth was the biggest country star of the 1990s.