5. Squeeze, "Tempted"

Squeeze is possibly the most underrated band of all time. And the fact that it took a few commericals to make this song into the hit it never was is lamentable. But lay cosmic injustice aside, and bask in one of the greatest odes to a wandering eye (and possibly wandering loins) ever written. Also, it's got something of a sense of humor to it, which you're no doubt craving by now, having made it this far in this list.

4. Dolly Parton, "Jolene"

In "Jolene," Dolly Parton doesn't have the strength or righteous anger of Loretta Lynn. What's she's got is a heartbreaking laundry list of the reasons her man is straying and one laid-bare plead to just leave him alone. It's a last-ditch move, laced with wheedling praise. It's the action of someone at the end of their rope, and Parton makes us feel every ounce of desperation.

3. Billie Holiday, "I'm A Fool To Want You"

Ray Ellis said that Holiday cried in the control room listening to playback from this song, and it's easy to understand why she might've. Lady in Satin was Holiday's second-to-last album, and she put a lifetime of misfortune and regret into every song. For anyone who's ever beat themselves up over "a love that can't be true / A love that's there for others too," it's hard to listen to this without feeling a little of what she felt in that room.

2. Stevie Wonder, "Part-Time Lover"

"Part-Time Lover" is another tune whose insane catchiness belies its subject matter. Stevie's escalating vocal performance is really what makes "Part-Time Lover" one of the all-time champs of catchy cheatin' tracks. Also noteworthy for a great final-act twist: the cheater becomes the cheatee. "I guess that two can play the game / of part-time lovers / You and me, part-time lovers / But, she and he, part-time lovers." 

1. James Carr, "The Dark End of the Street"

Some of the songs on this list are cavalier, some are angry, and a bunch are sad. But none manage to capture the spine-tingling combination of devotion and resignation this song nails. Carr is head over heels for his lover, but fully aware that they have no future. All he can do is keep heading back, hoping against hope for one more night. In some situations, that's all any of us can ask for.

 

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