The 50 Funniest Country Songs

While country music has its sad side as evidence by sad country songs there is plenty of humor to go around as well. Artists like Brad Paisley, Toby Keith, Roger Miller, Mindy McCready and others have filled country music fans with laughter and fun over the years.

Here is a collection of the funniest country songs of all time. These songs will make you smile, giggle, and even burst out laughing. If you’ve been in need of a good laugh you’ve come to the right place.


Funny Country Songs

50) Gotta Have My Java – Bryan White

Bryan WhiteBryan White is more known for his heartfelt country songs about love, loneliness and having a good time. In 2009 the former country star came back with a new set of songs including the fun little ditty Gotta Have My Java. The song is an ode to the dark brown drink so many need each morning to get ready for the day. The song takes a tongue-in-cheek twist on the topic of coffee and Bryan even sounds like he’s having a ball as he sings it. After taking some time off to raise his two young sons and be with his wife Bryan came back after a long break with a great new fun attitude towards music. Gotta Have My Java is a great song and one of the funniest country songs of all time because…well…we all gotta have it.

Listen to and Download Gotta Have My Java

49) One In Every Crowd – Montgomery Gentry

Montgomery GentryWe all know this guy. And as Montgomery Gentry says it is usually the two of them. One In Every Crowd is about the guy in the crowd that kind of annoys everybody else, but he’s always the life of the party nonetheless. The reason this song is funny is because we all have a friend or we are the friend that gets a little messy on nights out. They can usually tell the stories that make everyone else laugh and enjoy their time out on the town. We need these people even if it’s only for a few hours each weekend. Go along with the fun the next time your out with your own One In Every Crowd.

Listen to and Download One In Every Crowd

48) Guys Do It All The Time – Mindy McCready

Mindy McCready put a little twist on the guys in 1996 with her big hit Guys Do It All The Time. The song is about Mindy and her friends going out and doing all the annoying things guys like to do with no regard for their loved ones. These activities include heading out for more than just a few drinks, watching football all day and other things while leaving your woman at home usually tending to the kids. The song was done in good fun though and that’s a reason so many people loved it. It went all the way to the top and became a classic funny country song.

Listen to and Download Guys Do It All The Time

47) She Thinks My Tractor’s Sexy – Kenny Chesney

Kenny ChesneyBefore he was everybody’s favorite country beach bum Kenny Chesney had a little hit tune with She Thinks My Tractor’s Sexy. The song took a tongue-in-cheek twist on dating. Who would think to take their woman out for a ride on the tractor? Well if that gal just happens to think your tractor is sexy you’d better get her out on the fields for a few spins around the property. Kenny Chesney was the original guy to put a woman on a tractor, but you’ll have to wait until later on the countdown for another tractor song. Until then have a listen to this funny country song.

Listen to and Download She Thinks My Tractor’s Sexy

46) Weed With Willie – Toby Keith

Toby KeithIn 2003, Toby Keith released one of the biggest country albums of all time. Shock’n Yall was an in your face album and Toby didn’t hold back on his feelings with the album. While the album had hits about soldiers, bars, and whiskey it was an album cut that had fans buzzing. Weed With Willie was a fun song Toby co-wrote with fellow artist Scotty Emerick. The song is about having a little too much fun on Willie Nelson’s bus one night. It’s a fun song that poked a little fun at the fools that w0n’t leave Willie alone for his recreational activities. While Toby and Scotty couldn’t quite handle their encounter I’m sure they might venture back into funland with Willie someday.

Listen to and Download Weed With Willie

45) Bartender Song – Rehab with Hank Williams Jr.

Hank Williams Jr.Punk rocker Rehab added a few steel guitar licks and a little acoustic and turned his pop punk rock song Bartender’s Song (Sittin’ At A Bar) into a semi-hit on the country charts. The video caught some big play on CMT and GACTV. Having Hank Williams Jr join in on the track for the country version helped Rehab get introduced to the country audience. The catchy little tuned caught on with a select few country fans and had them smiling at the ridiculous lyrics that told the story of a guy on a bender. If you think about the song’s lyrics there is no doubt this story is country as well as being one of the funniest country songs of all time.

Listen to and Download Bartender (Sittin’ At A Bar)

44) With My Shirt On – John Michael Montgomery

John Michael Montgomery released his own album Time Flies in 2008 and it contained a hilarious song for all of those self-conscious middle age men out there. The song is With My Shirt On and it’s about wanting to make love to your woman but with your shirt on…you know…so she can’t see your beer gut hanging out. The song pokes fun at all of us that have a little tough time getting older and a little wider around the waist. It happens to just about everybody. As we relax in our later years we let a few extra pounds pack on. There is nothing wrong with that and there is no reason to feel ashamed.

Listen to and Download With My Shirt On

43) Pound Sign (#?*!) – Kevin Fowler

Kevin Fowler entered the country top 40 for the first time in 2010 with a David Lee Murphy penned tune. Pound Sign (#?*!) is a song about feeling like shhh… Well let’s just say that Kevin isn’t feeling too good and he shares the story with his fans. Kevin had been a huge star in his home state of Texas for many years before finally reaching the top 40. He had success writing songs for other artists and continued to tour and release music for his true fans in Texas. It took a good tongue-in-cheek song to finally get the deserving artist into the speakers of the wide country audience.

Listen to and Download Pound Sign (#?*!)

42) Ten Rounds With Jose Cuervo – Tracy Byrd

Tracy Byrd had himself a huge career in the ’90s. By the time the ’00s rolled around he was struggling to find hits with regularity. In 2002 though Tracy found a gem of a song with Ten Rounds With Jose Cuervo. The song is a story about heading out for a night on the town after a fight with a gal and having a bit too much tequila. The tune was catchy and fun and it had fans singing along. Tracy is still busy touring and Ten Rounds remains a fan favorite. It always gets people smiling and laughing along because they know they’ve been there.

Listen to and Download Ten Rounds With Jose Cuervo (Live Version)

41) Bubba Shot The Jukebox – Mark Chesnutt

Mark ChesnuttWe just read about Tracy Byrd. Here is his best buddy Mark Chesnutt with a classic funny country song. Bubba Shot The Jukebox is a classic Dennis Linde song. The tune tells the tale of Bubba, a guy that gets a little sad one night and shoots the jukebox at his local bar. The cops are called and the scene becomes something hilarious. Although the song is on the sad side there is just something hilarious about a guy named Bubba shooting a jukebox.

Listen to and Download Bubba Shot The Jukebox

Entire List

The Funniest Country Songs Part 2

The Funniest Country Songs Part 3

The Funniest Country Songs Part 4

The Funniest Country Songs Part 5

Dayne Shuda

Founder of Country Music Life. Follow on Twitter: @dayneshuda Follow on Google+: Dayne Shuda

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  1. Sooz says

    Obviously you haven’t been a fan of country music very long, since out of all 5 lists you only list a couple of artists who were around before the 80’s! And the biggest crime of all, you completely left out Ray Stevens, the funniest country singer of all time. His song, Mississipi Squirrel Revival, is the funniest song I’ve ever heard, in any genre! Before you set yourself up as an expert, at least attempt to know more than someone who doesn’t even LIKE country music as a rule!

  2. Heika says

    Why don’t you hop on off your high horse there Sooz and lighten up. So far I think this list is a fairly good one. You know what they say about opinions.


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