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20. Chris Isaak, "Wicked Game" (1989)
This song has one of the sexiest videos of all time, and that weird Elvis-aping hiccupy vocal tic is undeniably catchy. Isaak's vocal and and James Wilsey's guitar licks are live, but the rhythm tracks are loops constructed from previous takes — the way they push against each other is a little disorienting, and that gives the song a loose feel that perfectly paints a boozy night of regret. — A.H.
19. Janet Jackson, "Come Back to Me" (1989)
So much of Rhythm Nation is so stern and authoritative that when "Come Back to Me" drops, it's hard to believe this is our Dear Leader dropping her guard to plead with a departed lover. That juxtaposition makes it all the more effective, and all the more moving. — A.H.
18. Hüsker Dü, "Don't Want To Know If You Are Lonely" (1986)
With text messages and voicemail replacing the answering machine, the feeling of ignoring a call while listening to someone leave a message is gone forever. In ten years, your average post-grad will never know the feeling of listening to a 4 a.m. message come in from a recently departed boy/girlfriend. Luckily, they'll have one of the best Hüsker Dü songs to commemorate the experience. — Sean Morrow
17. Bob Dylan, "Most of the Time" (1989)
"Most of the Time" beautifully captures that nagging little voice inside your head that sneaks up on you at the most unexpected moments. "Don't even remember what her lips felt like on mine" — damn it, Bob, yeah, you do! — J.G.
16. REM, "The One I Love" (1987)
Here's a classic of the "frequently misinterpreted lyrics" genre. Michael Stipe says "The One I Love" is about "using people over and over again." In that sense, this is about not only giving up your lost love, but your own terrible habits as well. — J.G.