The 25 Best Cheating Songs from the Cheaters Themselves (25-18)

If you’re a regular here, you might have seen a few playlists that I’ve done in the past. Here are a few in case you missed them: Father Playlist, Grown & Sexy Playlist. I decided to make this one my most well-researched one yet. They couldn’t just be any songs, though. There are a million songs dealing with this subject. These songs had to be from the vantage point of the actual cheaters involved in the cheating. That also means that songs about being cheated on (i.e. Carrie Underwood’s “Before He Cheats”) did not make the cut.

Disclaimer: I do not in any way condone cheating. At the same time, this list is not intended to insight judgment. Songs inspired by strong emotion tend to be some of the best, so I felt that I would discover and rediscover a myriad of incredible songs. Obviously, I couldn’t put every good cheater song on here, but I certainly got a lot of them. Anyway, let’s get to it…

25. “She Don’t Have to Know” by John Legend – I could have used any number of his songs (“Number 1”, “Again”, “Another Again”, etc. However, I decided to go with this one because it captures that feeling of knowing you’re wrong, but lying to keep from getting caught.

Favorite Line: “Girl, I know you’re doing the same thing, too / But I won’t tell your man the things we do”

24. “Maybe I Deserve” by Tank – Tank put an interesting spin on this song by going around the fact that he cheated. He never actually admits it until towards the end of the song. Instead, he creates an imaginary tale of his girl doing what he did to her in real life. Impressive.

Favorite Line: “Maybe I deserve for you to say, ‘Yes, I cheated on you.’ / And I won’t care ‘cause after all I put you through”

23. “Second Chance” by .38 Special – I can’t help but laugh at some of these lyrics. It’s amazing how many feelings the same kind of act spawns. This song provides some of the weaker excuses for cheating, but it’s a good song, nonetheless.

Favorite Line: “I never loved her / I never needed her / She was willing and that’s all there is to say / Don’t forsake me; please don’t leave me now”

22. “The Other Woman” by Ray Parker, Jr. – “Who ya gonna call?” Well, if you’re Ray Parker, Jr., you’re obviously going to call the other woman. He messed up by falling in love with her, though. If you’re looking for a song filled with begging, pleading, and remorse, this ain’t the one for you.

Favorite Line: “Oh, this affair is unique / All my life I never met such a freak / She keeps going strong for so long / When I get home, it’s all gone”

21. “Human” by Human League – Now that I’ve established that some of these lyrics are weak, allow me to present Exhibit B. I get a kick out of some of the justification I read when I look at some of these lyrics. What’s the excuse for cheating in this song? “I’m only human.” Well, now that you said that…

Favorite Line: “I wouldn’t ever try to hurt you / I just needed someone to hold me / To fill the void while you were gone / To fill this space of emptiness”

20. “Unfaithful” by Rihanna – “Once a good girl goes bad, she’s gone forever.” RiRi wasn’t lying when she resurrected a Jay-Z lyric. Here, she is cheating on her lover, and he knows that she’s cheating on him. The worst part is that she’s happy with the other guy. Fortunately, she doesn’t want to cheat on him anymore. Out with the old, in with the new, I suppose.

Favorite Line: “I say, ‘I won’t be long. Just hangin’ with the girls.’ / A lie I didn’t have to  tell / Because we both know where I’m about to go / And we know it very well”

19. “Infidelity” by Trey Songz – This song is for the good lovesick girlfriends everywhere. Trey’s girlfriend loves him no matter what he does. He decides to do the admirable thing, which is to break up with her. “[She] can’t be mad at that…” Brutal. Poor girl…

Favorite Line: “With all my infidelity / You loved me so incredibly / Inside I’ll fall apart / If you ever love someone instead of me”

18. “You Know I’m No Good” by Amy Winehouse – Unhappily married and stuck together is how I’d describe this song in short. Amy goes back to an ex-boyfriend and does everything she can to make her seemingly dumb good husband divorce her. At least he knew what he was getting into.

Favorite Line: “Upstairs in bed with my ex-boy / He’s in a place, but I can’t get joy / Thinking on you in the final throes / This is when my buzzer goes”

Look out for songs 17-11 on the “25 Best Cheating Songs from the Cheaters Themselves” playlist tomorrow.

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