Lipstick on your collarAdultery is as old a concept as recorded history, at least as old as monogamy anyway. Moses didn’t care much for it when he presented his 10 Commandments to the Israelites (the first top-ten list?). And in our culture which treats monogamy and the sanctity of marriage pretty seriously as a result, cheating is treated as one of the worst things one person can do to another. And often times, it is. There’s no doubt that much damage has been done because of infidelity, creating powerful emotional states which range from despair, shame, helplessness, anger, regret, and sometimes a sense of emancipation too. And not all of those emotions are those felt by the one who has been done wrong. So, songwriters have had their work cut out for them with yet another universal human experience and set of emotions to explore in popular song.

So here are 10 songs about cheatin’, infidelity, adultery; 10 tales of mistresses, backdoor men, cuckolded husbands, betrayed wives, homewreckers, and philanderers served up for your pleasure.

Move it On Over – Hank Williams

Hank WilliamsWe’ll start with a tale of a man who learns that if you do the crime, you do the time. And in this song, being in the doghouse is a very literal reality, fleas and all. Hank Williams knew that both sexes would get a kick out of this tale of a man who is outdoors after promising not to “fool around/but (he) done let the deal go down”. This is the lighter side of cheating, a man who accepts the price as a matter of course, cuddling next to the dog when he couldn’t manage the restraint it took to overcome temptation in order to end up cuddling with his intended instead. Ultimately, this is comedy, not tragedy.

Hank Williams also knew that taking themes common to both black and white communities would allow his music to resonate on both sides of the cultural fence. This is a rock n’ roll song disguised as country – note the blues influences in this song. This is a stylistic cross-over, an example of Williams’ genius. This is one of those songs which is easily adapted to any era and any genre. George Thorogood & the Destroyers had a hit with it in 1978, but not before it was recorded by many other artists including Bill Haley & the Comets, Ray Charles, Del Shannon, and Willie Nelson.

Dark End of the Street – James Carr

James CarrIn some instances, cheating is a compulsion, not something that is even enjoyed, but is more like an addiction. In James Carr’s ‘The Dark End of the Street’, we find two lovers stealing moments, knowing that they’re doing the wrong thing, yet finding themselves unable to stop their illicit meetings. Where it’s often hard to take the side of the cheaters, this song proves that it’s not just the one cheated on who suffers. Sometimes, it’s the cheater, struggling with their darker impulses, and feelings the shame which involves confronting oneself and not liking what there is to see.

James Carr is not a household name like Marvin Gaye is, although the two were on the scene at around the same time. Yet this song, written byDan Penn and Chips Moman, has become bigger than his name, recorded by many other artists rangnig from Gregg Allman, to the Afghan Whigs, to Frank Black. It is a soul classic.

Love the One You’re With – Stephen Stills

Stephen StillsThere is a rule for many musicians that what happens on the road stays on the road. It was possibly out of this fluid state of morality that this tune by Stephen Stills emerged in 1970, a radio hit from his self-titled album. In this world which sits somewhere between reality and the rock n roll dreamworld, anything goes. And loneliness for a loved one who is far away is easily cured when the arms of someone new are temporarily proffered. The gospel strains of the tune help to push the idea along and somehow give it validity in a strange way, with a bit of contrast thrown in there for good measure – you’re not likely to hear this message in any church I know of. Yet in this song, it seems like the angels of heaven themselves are blessing the union of rock star and groupie, as if it were written in the stars.

One of my favourite versions of this song is by none other than Aretha Franklin who recorded it on her Live at the Filmore album in 1971, with Billy Preston rocking the hammond organ, and Bernard Purdie on the drums, among other excellent sidemen.

If Loving You Is Wrong (I Don’t Want to Be Right) – Millie Jackson

Millie JacksonBeing in an illicit relationship often creates feelings of shame and guilt. But, it can also cause a sense of defiance against those feelings too, that if one is trapped in moments of weakness, it must be because those circumstances are too big to control. Such is the case with Millie Jackson’s 1974 hit “If Loving You Is Wrong (I Don’t Want to Be Right)” off of her classic album Caught Up . In this song, the narrator is not interested in imposed morality, but is driven by the feeling that love is a higher calling, illicit or not. Yet there’s another thing that’s interesting here; that she acknowledges that her man’s wife ‘needs him just as much’. This is a portrait of a ‘homewrecker’, yet this woman has a human face, not a bad person necessarily, but rather one trapped by her own tenacity and depth of feeling.

This song is Millie Jackson’s signiture tune, from the standpoint of a woman who knows what she wants, even if it’s a man who is less than dedicated solely to her. There is a lot of grey areas here, which is often true in real life as much as it is in popular song. But Millie makes it entertaining, even if the subject matter has a lot of darkness to it.

Torn Between Two Lovers (Feelin’ Like A Fool) – Mary MacGregor

mary macgregorIt’s a wonder that someone hasn’t written an answer song called “Be torn no longer, ’cause I’m outta here, baby” to go along with this one, which was a huge radio hit in 1976. This one is very much of its time, in the era just after the sexual revolution, where women (and men too as it turns out) were discovering that there were levels of desire and need that perhaps couldn’t be fulfilled by just one person, or by other accepted norms when it comes to sex and relationships. Fair enough, if that’s what’s been established from the outset within your specific circumstances with someone else. But, this song is so perfectly framed as a time when “a woman has to say what’s on her mind, even thought she knows how much it’s going to hurt”. Put on your helmet, Charlie!

The story is told to one of the titular lovers who is being held “close” so that she can “say these words as gently as I can”, before she tells him that there’s been someone else, and will in fact continue to be someone else. She’s getting some by two different guys, and shes’ the one who feels like the fool! It’s done so gently and politely, that you can imagine the awkwardness of the moment after she finishes explaining things to him. I mean, after she’s been so honest about her need to continue shagging some other guy, it would be rude to get upset, right?

Tempted – Squeeze

Squeeze Eastside StoryThe price to be paid for infidelity is rarely considered in the moment. But, after the rush of it is over, the sinking feeling that you’ve paid too much with not much to show for it begins to set in. At least, this is what happens in this song by South-East London’s Squeeze. Being tempted by the ‘fruit of another’ leads to the loss of everything, leading to life with ‘no other’ to show for what has gone down between the sheets in the heat of passion. And the disorientation that follows is the kicker in this tune, the wondering what it was all for. The lilting Motown soul of the song belies the forlorn lyrics of a man undone by his own lack of awareness.

Taken from their 1981 Eastside Story album produced by Elvis Costello, the lead singer on this is Paul Carrack, who had been a member of a few bands, one being the band Ace who did a song called ‘How Long ‘ in 1975, which chronicled a betrayal of another kind – a band member leaving the group without being upfront about it. He would go on to sing on Mike & the Mechanics radio hit ‘The Living Years’, and Squeeze would break-up and rebound a number of times, the most recent reunion being this past year.

The Other Woman – Ray Parker, Jr.

Ray Parker Jr.Before he asked the musical question “who ya gonna call?” in his monster smash hit ‘Ghostbusters’, Ray Parker had a long career as a studio musician (Stevie Wonder, Gladys Knight & the Pips, The Spinners, and even Miles Davis) as well as a number of hits of his own. One of these was this one in 1982 – “The Other Woman” – which is kind of like a more macho, and less sympathetic (arguably) “Torn Between Two Lovers” as mentioned above. The narrator of this song is one who is caught off guard when he realizes that the brief dalliance with another woman which he engaged in as a matter of course (an ‘average guy’ who ‘fooled around a little on the side’) has become a lot bigger than he planned, not expecting to be caught as he is in a situation where “a one night stand/could turn into such a hot romance”.

One of the interesting things about this song is how this is treated as a pleasurable inconvenience, rather than a real problem which risks loss, or someone getting hurt. Even the situation described in Millie Jackson’s tune doesn’t apply here. This guy isn’t raging against the machine which keeps illicit lovers who are really in love apart. Nor is he suffering at the Dark End of the Street like James Carr. No. This guy can’t believe his luck. As such, this is pure fantasy, a cleaned-up Penthouse letter. So, you can understand why it was a successful pop song – reached #2 on the Billboard R&B chart! Yet in contrast to this song, he wrote and performed another hit called ‘A Woman Needs Love (Just Like You Do)’ which is a song about a guy advising another guy to stop cheating, lest his betrothed start stepping out herself.

Into Temptation – Crowded House

Crowded HouseOne of the characteristics of infidelity is that it can be boiled down to a single moment, the few seconds it takes to consider temptation and reject it, or embrace it. The best defense against giving in to temptation is often by being aware you are in fact being tempted. And even then, it’s a pretty uncomfortable place to be. In this 1988 Crowded House song “Into Temptation” from the album Temple of Low Men, songwriter Neil Finn depicts such a moment, a brief instant when the door to temptation is open, just waiting for the narrator to walk through it – “you opened up your door/I couldn’t believe my luck/you and your new blue dress/Taking away my breath.”

This is a moment of truth song, a song that deals with being tested to see whether or not one is as good as one’s word. a time when your whole world is at risk depending on your choice in the moment – “knowing full well the earth will rebel”. You can get the impression by the end that the narrator falls down, being guilty and getting no sleep in the “last few hours of morning/ experience is cheap/I should have listened to the warning”. But, it could be that temptation was overthrown, and that the experience has caused a re-evaluation of his values; that it was the fact that he almost gave in that makes him feel guilty. Neil Finn is a skillful songwriter, and that this is an open-ended question with few easy answers demonstrates this here as well as anywhere.

The Other Man – Sloan

SloanThere has been a lot written about the Scarlet Woman. But there haven’t been too many songs about the Scarlet Man. In this song by Sloan from their 2003 album Action Pact, we get the portrait of a friend who has “crossed the line”, the figure who many men dread as being a part of the lives of the women they love because to find such men threatening often reflects badly on them. As such, when the line is crossed, there are two betrayals; the women betraying her partner, and that of the Other Man who betrays the idea that men need not fear their wives and girlfriends having straight, male friends.

Yet there is another level here; that the rot which sets in after a relationship has come a certain distance has nothing to do with the one with whom the woman cheats. – “you know he’s not the one for you, but that’s no fault of mine.” This is not a man who necessarily wants her to leave her lover and run to him, but rather that he knows that she is being dishonest whether he is in her life or not, and wants her to face up to it before her lover finds out about her infidelity. The point is made that the one with whom another cheats is usually not the one with whom most people sympathize. In this song everyone in the triangle is being dishonest, including the cuckolded husband who knows “you’re going to drift apart and there’s nothing he can say”. This song is about shifting blame back and forth, with a conclusion that sometimes in these situations, everyone is guilty of something.

You Know I’m No Good – Amy Winehouse

Amy WinehouseJudging the cheater often falls along gender lines, I find. When a woman cheats, it’s because she’s not getting what she needs from her man on an emotional level. When a man cheats, he’s just giving into base desires. Very subtly in this narrow context, women are seen to being forced into cheating, where a man has to be forced not to cheat. But in Amy Winehouse’s ‘You Know I’m No Good”, it’s pointed out that base desires are very much alive and kicking in a woman as much as they are in a man. And what drives a woman to weakness when trying to remain faithful may have nothing to do with what her betrothed is or isn’t giving to her in their relationship. Sometimes, Amy points out, women are scoundrels too.

But, apart from base desires question, there is still the question of self-loathing here, which is another strain talked about in this song. The narrator cheats, but she finds out that she “cheated myself/like I knew I would”. This is not just about betraying someone else; it’s about betraying oneself. In this song, cheating is a symptom of something greater, a larger problem that perhaps remains to be addressed. The temptation to apply this idea to Winehouse herself is pretty strong, of course, well acquainted as she is with the dark side of life as reported in the tabloids. But, I think this can be applied to infidelity in general, that it is not really the problem, so much as a symptom of one.


Infidelity has been an issue since civilization began, and has certainly been recorded in our most popular literary myths; David & Bathsheba, Marc Antony & Cleopatra, Guinevere & Lancelot, Tristan & Isolde, and many others. What is clear is that cheating at it’s worst causes damage that ripples outward like the aftershocks of an earthquake, often causing irreparable damage to innocent parties. At it’s best though, it challenges our ideas of what commitment means to us, and forces us out of a place where we take relationships for granted. And maybe through stories and song, this is the best means of keeping things on track. At very least, the fact that infidelity has been a part of the human experience for so long can give comfort in times of trial, because we can rest in the knowledge that we’re not the first to face it. Maybe, songs and stories can even teach us a lesson or two. Who says art is useless?

25 thoughts on “10 Songs About Cheating

  1. The Cheatin’ song that comes to mind for me is “Me and Mrs Jones” by Billy Paul.
    I think it came out in the seventies and now I think Michael Buble has remade it.

  2. Oh yes!….Amy Winehouse must be on the list but, in my opinion, for different reasons. Have you ever heard her live version of ” I heard Love is Blind”? One of the most beautifully written songs, a cheater consoling the cheated. It’s on her “Back to Black” album, but the live version is at a slower tempo and brings the song to life with a vibrant horns section and sultry guitar: an altogether different feel. DEFINITELY! Listen to the live version! (try “Live in Paradiso” album). Click this link and take my word for it.

  3. Thanks a lot for that clip, AmirandaJ.

    Winehouse is an incredible vocalist, and here she’s less Etta James and a bit more Billie Holiday. This song is actually from her pre-tabloid fame album Frank (note the lack of tattoos, and the normal body weight in the clip…). And you’re right; this live version is pretty powerful.

    Thanks again!

  4. Oh, my…you are absolutely right! I did misquote the album! Slap my wrist and call me naughty. Thanks for the correction Rob. And so ensues the kindergarten crush…

  5. Nice post, with some interesting, off-the-beaten path selections, and thoughtful comments, too. Am researching for a show on ‘the other man,’ and came across your site.

  6. I assume you mean Sloan. Yep, they are a terrific band. Four great pop songwriters and performers that most people haven’t heard (at least around my neck of the woods).

    About my show: Thanks for asking. I’m one of the many college deejays who get a little chunk of time each week to do something interesting on air (I hope)!

    The Sunday Sampler with Marc Morrison on WIUP-FM
    Sundays from 8-10pm (EST)

    1. Thanks, Whiley. I was looking for a reference to this song. I love me some Robert Cray, and this is one unexpected twist of a cheating song. Cray accepts all responsibility in this one. Mmm.. Far too many women would volunteer to be another notch…

  7. I enjoyed your list. But one of my fav songs of all time is about cheating and may not be worth being on the list, but I wanted to mention it anyway. The thunder rolls by garth brooks, specifically the live version with the extra verse.

  8. can you identify a modern jazz song that goes something like this “My baby likes to fool around”,
    or play around, she is a hooker obviously?

  9. Everyone always misses the best, most intriguing, most soulful song about cheating: Bill Withers’ “Who is He and What is He to You?” That song runs deep.

  10. Me and Mrs Jones is still my fave. However Amy Winehouse does a sort of version called me and Mr. Jones and its differnet but the message is the same.

What are your thoughts, Good People? Tell it to me straight.

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