Affair deal: 20 essential songs about cheating

Appearing on Carrie Underwood's 2005 debut, this barn-burner of a cheating song is written from the perspective of the woman that's been done wrong and is out for revenge — complete with a Louisville Slugger to the headlights. 

A #1 hit for Whitney Houston in 1999, "It's Not Right, But It's Okay," is about a woman who's fully come to terms with her philandering man's bad behavior, and is on her way out the door. 

Arguably one of the first and most legendary cheating songs in American music, Hank Williams's "Your Cheatin' Heart" was released in 1952. It's a real tear-jerker of a tune, one that's a reminder that cheating comes with consequences for everyone involved, including the cheater. 

This iconic 1994 R&B track is all about a woman who's getting back at her cheating lover by having an affair of her own, or as the song says, "creepin' on the down-low." "Creep" sparked plenty of controversy, even among members of TLC, who worried that its message should be more focused on telling women to get out of bad relationships. 

This song, written by Don Henley and Glenn Frey, was inspired by some actual cheating that the duo observed in a bar. It posits that no matter how good of a cheater you are, you can't hide the guilt in your "Lyin' Eyes." 

The romantic drama within Fleetwood Mac, especially the tumultuous relationship between Lindsey Buckingham and Stevie Nicks, is the stuff of legends. "Go Your Own Way" is about the duo's breakup, and Nicks originally protested the inclusion of a lyric that implied that all she wanted to do was go "shack up" with other men. 

This massive 2003 hit was based on a true story of cheating, in which The Killers frontman Brandon Flowers recounts finding his girlfriend in a bar in Las Vegas with another man. Clearly, it resonated, and now "Mr. Brightside" is one of the most-streamed songs in music history. 

Some argued that Justin Timberlake went a little too over-the-top with the music video for "Cry Me A River," which featured an actress who looked a whole lot like his girlfriend at the time, fellow pop star Britney Spears. Rumors swirled that Spears had been involved in an affair with a choreographer, which she vehemently denied. Whatever the truth, "Cry Me A River" is definitely an iconic cheating song. 

An all-woman riff on an '80s duet between Michael Jackson and Paul McCartney, "The Boy Is Mine" was inspired by dramatic love triangles that co-writer Brandy Norwood saw on the "Jerry Springer Show," which just feels so totally '90s. It's unclear who the cheater is here, but one thing is certain: this duet remains one of the most iconic R&B tunes of the '90s. 

A critical and commercial success for Amy Winehouse in 2007, "You Know I'm No Good" is rooted in the singer's personal struggle with substance use and her own tumultuous relationship. "I told you I was trouble," she sings on the chorus. "You know I'm no good." 

This Sugarland song is a whole cheating journey. It follows a woman who's having an affair with a married man as she begs for him to stay instead of heading home to his wife, then finds the strength to walk away when she realizes that she can do better. 

Kurt Cobain called this song "Where Did You Sleep Last Night," but it's a 100-plus-year-old blues tune that also holds a morbid place in the band's history. It's a murder ballad about a man who's just found out that his wife's cheating on him, and the last song that Cobain performs on the band's legendary "MTV Unplugged" appearance just months before he died. 

A particularly violent version of the classic done-me-wrong song, Jimi Hendrix's first single with the Jimi Hendrix Experience is about a man who's looking to kill his girlfriend after finding out that she's been less than faithful. 

"Confessions Part II" makes it pretty clear up front that this is a song about infidelity. In the track, Usher confesses to getting his mistress pregnant and was inspired by songwriter Jermaine Dupri's own life. 

Dolly Parton seeks to nip any potential cheating in the bud on "Jolene," which she has said was inspired by a female bank teller who hit on her real-life husband, Carl Dean. It's arguably one of country music's most iconic songs, and that's saying a lot in a genre replete with them. 

The cheater gets the spotlight on "If Loving You Is Wrong, I Don't Want to Be Right," a 1972 Luther Ingram hit that's all about knowing that the cheating you're doing is wrong but being so into your lover that you just don't care. 

The subject of this 1994 Shania Twain hit really got around, leaving his boots under the bed of women all over town. There's Rita, Jill, and of course, Beverly Hill, and Shania's had enough. "So next time you're lonely, don't call on me," she sings. "Try the operator, maybe she'll be free." 

This 2012 Euro-pop anthem is as audacious as it is catchy. In the lyrics, Robyn tells her paramour that it's time to let his girlfriend know that he's ready to move on with her. She does, at least, ask him to "let her down easy." 

This 1993 duet between Linda Davis and Reba McEntire is written from the perspective of both women involved in a love triangle. In addition to its deeply dramatic lyrics as the two try to determine who the man in question actually loves, "Does He Love You" also inspired a truly iconic music video complete with a cameo from director Rob Reiner. 

Reggae one-hit-wonder Shaggy's friend literally gets caught in the act of cheating on this 2000 smash-hit and somehow still manages to deny that he's being unfaithful. Even after getting busted butt-naked on the bathroom floor!