90s Country: Top 10 Songs About Cheating

by Jacklyn Krol

Country music is known for being able to perfectly articulate the scorn of a cheated lover. Discover a list of the best songs about cheating from the 90s.

Without further ado, here are the top 10 songs from the most memorable decade of country music, the ’90s.

10. “A Woman Know” – Kenny Chesney

Kenny Chesney debuted “A Woman Knows” on his 1999 record, Everywhere We Go. The song tells the story of a woman who has been cheated on from a man’s perspective.

The narrator is looking at the situation from the outside and shows that the woman knows she is being cheated on. It’s not your typical cheating song and shows the hurt that it can inflict.

9. “Wish I Didn’t Know Now” – Toby Keith

Toby Keith’s “Wish I Didn’t Know” sums up one of the stages a couple goes through when cheating is involved. Keith sings about trying to ignore the signs of cheating before realizing that he rather love blindly than without her.

The song was written by Keith for his 1994 self-titled debut album. The song reached No. 2 on the Billboard Hot Country Songs chart and No. 17 in Canada.

8. “Alibis” – Tracy Lawrence

Tracy Lawrence sings about his woman dealing with his lying and cheating ways. He knows that she knows every alibi and trick in his book and that she used to believe that love wasn’t a game. He knows what he’s put her through yet he continues to do so.

The single was written by Randy Boudreaux and released for his 1993 album, Alibis. Overall the song became Lawrence’s second No. 1 smash.

7. “She Just Started Liking Cheatin’ Songs” by Alan Jackson

Alan Jackson sings about his woman who has a new affinity for songs about cheating. He doesn’t know if it’s the melody or the lyrics she enjoys. He hasn’t seen any signs of cheating or deceit but he wonders if his love is enough. Jackson has sung his fair share of cheating songs, like “Who’s Cheating Who?”

The song was written by John Anderson and Kent Robbins. The song was originally recorded by Anderson for his self-titled 1980 record. It reached No. 13 on the Billboard Hot Country Songs Chart. In 1999, Jackson covered the song for his record, Under The Influence. Surprisingly, his cover reached No. 72 on the charts without it being a single.

6. “Soon” – Tanya Tucker

Tanya Tucker brings all of the emotion on “Soon.” The single was written by Bob Regan and Casey Kelly. It acted as the first single and title track from her 1993 album. Overall, it reached No. 2 on the Billboard Hot Country Singles Chart.

The song tells the story of a woman who is having an affair with a married man. The man claims that he will break up with his wife and be available for her soon. By the end of the song, the woman realizes that he will not leave his wife.

5. “Let That Pony Run” – Pam Tillis

Pam Tillis recorded “Let That Pony Run” for her 1993 album, Homeward Looking Angel. Moreover, the song peaked at No. 4 on the Billboard Hot Country Singles chart.

The main character of the song is Mary, who is a wife and mother. Her husband came clean about his cheating ways with a barmaid with the help of Jim Beam. Tillis urges her to hang on until she can’t anymore and let him run. The woman got a divorce and moved on. We find her character living her best life with a horse, running free.

4. “I Guess You Had To Be There” – Lorrie Morgan

Lorrie Morgan knows how to pack on the guilt with this tune. “I Guess You Had To Be There” was written by Jon Robbin and Barbara Cloyd. The track was featured on her 1993 album, Watch Me. The song peaked at No. 14 on the Billboard Hot Country Singles chart.

Morgan welcomes her husband home and talks about a couple she saw while out in the town today. She compared the new woman to what she and her husband used to be like. The song concludes with, “What’s the matter, you don’t have much to say?”

3. “The Thunder Rolls” – Garth Brooks

Garth Brooks tells the story of a woman who discovers her lover has been cheating on her. A thunderstorm is brewing while a woman waits for her man, who is late coming home. She is praying that he is safe and that he isn’t cheating. Once he comes home she smells a new perfume on him. The thunder rolls in her heart for his deceit.

Tanya Tucker first recorded the song. She never released it until her 1995 greatest hits box set. Unlike Brooks’ version, Tucker’s rendition featured a fourth verse.

This became Brooks’ sixth No. 1 hit. Aside from it first appearing on his No Fences album, it was also featured on The Hits, The Limited Series, Double Live, and The Ultimate Hits.

2. “Does He Love You?” – Reba McEntire and Linda Davis

Reba McEntire and Linda Davis teamed up for an epic duet and music video. The song depicts a love triangle between two women and an unfaithful man. The ladies aren’t sure who he really loves at the end of the day. The music video shows off Davis and McEntire’s acting chops.

Sandy Knox and Billy Stritch wrote the heart-aching track. The single appeared on McEntire’s compilation album, Greatest Hits Volume 2. The duet was so popular that it won the Grammy award for Best Country Vocal Collaboration. Additionally, it took home a CMA award for Vocal Event of the Year.

Honorable Mentions

“Broken Promise Land” – Mark Chesnutt

Mark Chesnutt knows he’s a cheater and in bed with another woman, a space he calls the “broken promise land.” He comes home to find his faithful wife has left him.

“All These Years” – Sawyer Brown

A couple realize what they have to lose after all of these years together with their family. He details a story of a man walking in on his wife with another woman, and the fallout of emotions thereafter.

“Rumor Has It” – Reba McEntire

McEntire knows her way around a cheating liar. The song is also the title of her 1990 studio album. She details rumors that she hears about the other woman.

The No. 1 Country Cheating Song

Shania Twain has the No. 1 cheating song with “Whose Bed Have Your Boots Been Under?” The quick-witted song uses playful banter with a honky-tonk vibe. Twain questions her beau if he has been cheating and with who since his boots aren’t under her bed.

The song became Twain’s first Gold-certified single. The song is off of her second studio album, Woman In Me. This song arguably shot Twain into country superstardom. In 1995 the tune reached No. 11 on the Billboard country music charts.