Pop Will Eat Its Children, Pt. 3

40. "Still Not a Player," Big Pun

1998
U.S. Billboard Hot 100 Peak Position: #24

Pun was one of the best at what he did. His so-called "club" songs were every bit as lyrical as his "street" tracks. The late, lamented MC wasn't simply lyrically dexterous, he was funny. Over come-hither licks 'n' clicks, Pun boasts about his penchant for pussy-tasting and ass-regulating, making sure to remind the listener: "I'm not a player, I just fuck a lot."

Keep it? YES

39. "Brand New Love," Sebadoh

1992
U.S. Billboard Hot 100 Peak Position: Did not chart

Sheffield and his soft spot for…well, it's just a soft spot, really. (Non-sociopaths tend to have them.) "Brand New Love" was originally recorded in 1987, then re-done for the Sebadoh Vs Helmet EP. Risks are inherent with any surgery, especially open-heart procedures, and especially when performed by a doctor high off his ass.

Keep it? NO

"Beauty of the Ride," Sebadoh

1996
U.S. Billboard Hot 100 Peak Position: Did not chart

Lou Barlow gives the impression of caring just enough to keep from going over the edge. His lyrics expose the emotionalism his voice tries to conceal. Frequently, they also contain solid advice: Don't defuse the bomb. Do keep one eye on the timer.

38. "Mind Playing Tricks On Me," Geto Boys

1991
U.S. Billboard Hot 100 Peak Position: #23

The Isaac Hayes is so pristine, I almost didn't want to hear anyone rapping over it. Silly me. The Boys gained notoriety for lyrics full of murder and misogyny, but their most indelible work is their most thoughtful, and one of the genre's standout storytelling songs: spooky without veering into corniness, fantastical yet completely authentic.

Keep it? YES

37. "You Get What You Give," New Radicals

1998
U.S. Billboard Hot 100 Peak Position: #36

The Nineties version of the "woke" white boy. How such a putrid pep talk resonated with so many baffles me. Joni Mitchell came out in praise of this song, and Joni Mitchell comes out in praise of nothing.

Keep it? NO

"Enjoy the Silence," Depeche Mode

1990
U.S. Billboard Hot 100 Peak Position: #8

Violator came out in '89, which better be Sheffield's reasoning for leaving this off his list. I love this song so much, it doesn't even bother me that it basically advocates the elimination of words. The Anton Corbijn-directed video looks like the Plow King in the midst of an existential boring change.

36. "Glory Box," Portishead

1995
U.S. Billboard Hot 100 Peak Position: Did not chart

Trip-hop hip-lock with a lesson: a woman is a woman once baptized in her own melted gold.

Keep it? YES