Thanks for reading through the first 3 parts of the series. Will your favorite songs be in Part 4?
100 Greatest Country Songs of the ’90s – 40 to 21
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.