5 Contagious Country Songs That Perfectly Toe the Line Between Funny and Serious

Sometimes, I feel like country music as a whole takes itself too seriously. So many artists are overly concerned with telling everyone how country, in love, or “authentic” they are in songs that come off as corny. Then, there are the novelty songs that are silly but the humor ends up feeling forced. Rarely, do songs find the balance between serious and funny without being cornball novelty tracks.

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The songs below put a smile on my face every time I hear them. I hope they’ll do the same for you.

“Trashy Women” by Confederate Railroad

Some would say this song by country rockers Confederate Railroad is corny. Those who lack a sense of humor may say it didn’t age well. I, on the other hand, love this tune.

Outlaw Country legend Jerry Jeff Walker was the first to cut “Trashy Women” but my introduction to the song came by way of Confederate Railroad’s version getting moderately heavy airplay in the early ‘90s. The first time I heard it, it got stuck in my head and I went around singing it to myself for days on end. Decades later, “Ain’t she cool? That’s the kind I dig!” is still one of my favorite lines from any song.

 “Thank God and Greyhound” Roy Clark

Brad Paisley’s “I’m Gonna Miss Her (The Fishin’ Song)” is a top-tier breakup song. I like to think of Roy Clark’s “Thank God and Greyhound” as that song’s cooler older brother. I would find it hard to believe that Paisley and his co-writer Frank Rogers didn’t take some inspiration from this classic.

It starts as a slow, sad waltz about a relationship that is both toxic and failing. Then, the twist comes when Clark sings Thank God and Greyhound you’re gone. The song’s mood completely shifts and becomes a celebration of freedom.

“In Spite of Ourselves” by John Prine and Iris DeMent

John Prine is my favorite songwriter and this song is part of the reason I love his work so much. Country music is packed with sappy love song duets that can verge on corny. You know, the kind of songs that play at weddings while the happy couple dances and their families wipe away tears. This isn’t that.

“In Spite of Ourselves” may not seem quite as sweet on the surface, but it is. The “couple” in the song snipes at one another but the jabs are all good-natured. It is both an example of how far humor goes in a loving relationship and Prine’s ability to find the joke in serious subject matter. If there comes a day when my wife and I don’t sing along to this one when it comes on, we’ll be looking for a marriage counselor.

“You’re the Reason Our Kids Are Ugly” by Loretta Lynn and Conway Twitty

For my money, no one cut better duets than Loretta Lynn and Conway Twitty. They sang so beautifully together that many believed they were an item. I wouldn’t be surprised if some still hold on to that belief today. Songs like “As Soon as I Hang Up the Phone” and “I Can’t Love You Enough” are certified classics. Then, there’s “You’re the Reason Our Kids Are Ugly.”

This one falls in the same camp as “In Spite of Ourselves.” Lynn and Twitty portray a couple who is very much in love no matter how crazy they drive one another. However, it’s not one that becomes a hand-holding, sly-grinning karaoke session when it comes on in the car. Instead, the track is a barrel of laughs from beginning to end. It never gets old.

“I Think She Only Loves Me for My Willie” by Paul Overstreet  

Paul Overstreet wrote some of the greatest country songs of the 20th century. For instance, he wrote Randy Travis classics like “Forever and Ever, Amen” and “On the Other Hand.” He also penned Keith Whitley’s “When You Say Nothing at All” and The Judds’ “Love Can Build a Bridge.” The list goes on. If your favorite song came out in the ‘80s or ‘90s, Overstreet might have a writing credit on it.

However, he showed a different side of himself with “I Think She Only Loves Me for My Willie” from his 2008 album Something for the Road. The track is about a lady who falls for the song’s narrator after hearing him do his best Willie Nelson impersonation. However, the song is packed with enough double entendres to make my inner 12-year-old double over with laughter.

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