In love triangles, the usual laws of geometry do not apply. There are never just three angles—not when all involved parties (cheaters, victims, homewreckers) feel a range of emotions constantly subject to change. All that complexity has made for some terrific pop tunes, and what follows are 15 of the best songs about cheating. Lovers come and go, but these classic tales of infidelity will stick around forever.
"Your Cheatin’ Heart," Hank Williams
The grandpappy of all cheating songs, this deceptively simple honky-tonk weeper goes light on details and heavy on feelings. Is ol’ Hank a wronged husband or boyfriend warbling plaintively to his philandering missus, warning her of what she’s about to lose? Or is he some lovesick would-be homewrecker making his case to a married lady who won’t leave her man. Either way, it’s a triple-shot of sadness as only Hank can deliver.
Chart Peak: No. 1 on the Best Sellers in Stores & Most Played by Jockeys country charts beginning 4/11/53
“I might as well take a gun and put it to his head,” sings Ri on this mea culpa from a serial two-timer. In situations like this, the cheated-on party doesn’t have the monopoly on feeling crummy. At least Rihanna gets some sexy rendezvous to go with all the pain and guilt she pours into this ballad.
Chart Peak: No. 6 on Billboard Hot 100, 7/22/06
"Before He Cheats," Carrie Underwood
Playing against type, good girl Carrie Underwood goes the hell-hath-no-fury route on this pop-country revenge fantasy. While her man’s putting the moves on some Shania wannabe with no taste for whiskey, Carrie’s in the parking lot, giving his truck a makeover.
Chart Peak: No. 8 on the Billboard Hot 100, 6/2/07
"Cry Me a River," Justin Timberlake
Reportedly inspired by JT’s breakup with Britney Spears, this slick R&B bumper is about refusing to forgive and forget after being cheated on. “The bridges were burned,” Timberlake sings, saving his dignity from a similar torching. “Now, it’s your turn to cry.”
Chart Peak: No. 3 on the Billboard Hot 100, 2/1/03
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"Jolene," Dolly Parton
Proof of why Dolly’s such a terrific songwriter, “Jolene” isn’t about anger, revenge, or any of the feelings typically associated with cheating songs. Fearing she’s about the lose the only man she’ll ever love, Dolly tries to bargain with the object of her husband’s desires, asking the auburn-haired, green-eyed temptress to work her charms someplace else: “Please don’t take him just because you can.”
Chart Peak: No. 60 on the Billboard Hot 100, 3/2/74 (and No. 1 on Hot Country Songs, 2/2/74)
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"Long Black Veil," Johnny Cash
Written by Danny Dill and Marijohn Wilkin and recorded by numerous artists, “Long Black Veil” seems tailor-made for Johnny Cash. Sung from the POV of a dude who’d rather hang for a murder he didn’t commit than tell everyone he was getting busy with his best friend’s lady the night of the crime, this one’s got everything: screwing, killing, lying, supernatural phenomenon, and questions of morality with no easy answers.
"Me and Mrs. Jones," Billy Paul
Billy really needs to put a stop to this “thing going on” between him and Mrs. Jones. It’s killing him to only see her for brief cafe dates, and since they both have “obligations”—i.e. spouses and kids—they’re never going to be together. Still, Billy savors every bittersweet moment while he can, which is why he takes about 45 minutes to sing that four-word chorus.
Chart Peak: No. 1 (three weeks) on the Billboard Hot 100, 12/16/72
"Runaround Sue,” Dion
One of rock’s original slut-shaming songs, this 1961 smash warns of a girl who’ll love you, leave you, and basically treat you like Dion treats girls in “The Wanderer,” the single he released right after this one. Maybe Sue was just looking for a guy who doesn’t subscribe to bogus double standards.
Chart Peak: No. 1 (two weeks) on Billboard Hot 100, 10/23/61
"O.P.P," Naughty by Nature
For those who grew up in the ‘90s, learning what that second “P” stands for was a rite of passage. The generally accepted meaning is “other people’s property,” though rapper Treach alludes to some dirtier alternatives. No matter the meaning, “O.P.P.” is a song everyone can and should be down with.
Chart Peak: No. 6 on the Billboard Hot 100, 11/9/91
In the ‘90s, few sounds were sexier than the horns on this seductive R&B ode to getting action on the side. The ladies of TLC don’t mean to be unfaithful. It’s just that their men are running around with other ladies, leaving their needs unfulfilled. So they creep—and rightfully so.
Chart Peak: No. 1 (four weeks) on the Billboard Hot 100, 1/28/95
"You Know I'm No Good," Amy Winehouse
At least Amy gives her man fair warning in this 21st century take on old-school R&B. “I told you I was trouble,” she sings throughout the song, stopping short of apologizing for each roll on the carpet with her “ex boy.” In the end, all her man can do is shrug—either because he no longer cares, or because he’s engaging in some extracurricular activities of his own.
Chart Peak: No. 77 on the Billboard Hot 100, 3/1/08
"It Wasn't Me,” Shaggy
As English singer Rikrok ponders how to proceed after being caught “buck naked on the bathroom floor” with another woman, he doesn’t get the benefit of having both an angel and a devil on his shoulders. His only advisor is reggae-pop crooner Shaggy, a devilish ladykiller who offers but one piece of advice: deny everything. Thankfully, Rikrok’s conscious kicks in by the final verse, where he opts to apologize and renounce his player ways.
Chart Peak: No. 1 (two weeks) on the Billboard Hot 100, 2/3/01
"I Heard It Through the Grapevine," Marvin Gaye
The interesting thing about this Motown classic -- a hit for both Marvin Gaye and Gladys Knight & the Pips -- is that it might not actually be a song about infidelity. “People say believe half of what you see,” Gaye sings on his definitive version. “And none of what you hear." So maybe the rumors about his lady aren’t true. Gaye’s impassioned performance leaves room for at least a little hope.
Chart Peak: No. 1 (seven weeks) on the Billboard Hot 100, 12/14/68
"Who's Making Love," Johnnie Taylor
Having learned the hard way that when the cat’s away, the mice will play, Taylor offers a warning to two-timing fellows on this brassy Stax classic. “Who’s making love to your old lady, while you’re out making love?” he asks, changing the narrative in such a way that women aren’t just passive victims wondering when their men will come home.
Chart Peak: No. 5 on the Billboard Hot 100, 12/7/68
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"Whose Bed Have Your Boots Been Under?” Shania Twain
If Shania’s mad at this guy for knocking boots with ladies all over town, she doesn’t really show it on this perky country tune. Oh, she’s kicking his butt to the curb (“So next time you’re lonely, don’t call me”), but she’s doing so with a smile—and a rather detailed inventory of his many conquests.
Chart Peak: No. 11 on Hot Country Songs, 4/29/95