Everybody makes mistakes — and the greatest rappers of all time are no exception. With so much ink dedicated to lauding the brilliance of the genre’s game-changers, here’s a look at a few singles that represent the worst from the best. Lots of albums — even classics — have clunkers on them, but when you release a track to radio that’s bad, it achieves a special kind of infamy. These are some of those terrible singles:
10. “All of Me” by Big Daddy Kane (1990)
We don’t talk about it enough, and it’s no diss to one of the greatest rhymers of all time, but Big Daddy Kane’s fall off was one of the steepest and fastest in hip-hop history. The Brooklyn legend’s first two albums are classics, but his third one, released just over a year after his seminal second album, It’s A Big Daddy Thing, turned off many of his fans. The worst offense was this sappy, cornball duet with the legendary Barry White that was actually the album’s highest charting single. Says more about the album than it does the single.
9. “Shut ‘Em Down” by LL Cool J (2000)
LL’s early 2000s music was pretty crappy, and this self-produced lead single from the Any Given Sunday soundtrack was one of his crappiest. With LL rhyming about how he can “bump and grind out, pump the lines out,” and screaming football-ish wide receiver-speak like “Get off me!” and “You can’t hold me!” on the hook, The song hit the charts with a thud and LL went scrambling back to loverman duets with Jennifer Lopez
8. “You Can Do It” by Ice Cube (2000)
Cube had spent the ’90s as, first, a fiery gangsta prophet with a knack for both socially aware content and scathing misogyny; and, second, as a crossover movie star, with hit films like Boyz N the Hood under his belt. But in the late ’90s/early 00s, he dabbled in club fare, and while “We Be Clubbin” may be the more infamous example of his worst period, this gangsta aerobics anthem actually better represents how bad it got.
7. “All Day” by Kanye West w/Paul McCartney (2015)
This single was almost good. It has all of the bombast of latter day Kanye but not much of the melodicism that marks his best stuff. And the production seems to have too many cooks in the kitchen, not to mention a McCartney coda that feels like it was beamed in from an entirely different song. The track’s debut got fans buzzing but it didn’t exactly deliver on the promise of Yeezy and Macca’s previous collabo — the Rihanna hit, “FourFiveSeconds.”
6. “On Fire” by Lil Wayne (2008)
Nobody was really expecting to take Lil Wayne’s rock album all that seriously after it was announced that the YMCMB superstar was going to be indulging his guitar fetish on an entire album. The result was more Kid Rock than Keith Richards and this single, which samples the lame ’80s throwaway “She’s On Fire” by Amy Holland, which appeared in Scarface, a film that has a famously bad soundtrack.
5. “Snoop’s Upside Ya Head” by Snoop Dogg (1996)
Snoop’s early ’90s run of excellence was getting quite wobbly by 1996. Death Row was in the midst of intense turmoil with the defection of Dr. Dre, Suge Knight’s legal issues and the addition of the controversy-baiting Tupac Shakur. In the midst of the mess, Snoop — who’d just beaten a murder case, by the way — was trying to record the follow-up to his uber-classic debut album, Doggy Style. Unfortunately, the result was substandard, uninspired G-funk and the lead single was this goofy interpolation of a Gap Band hit that also features Charlie Wilson, who comes off like your uncle trying to be “cool” at the family reunion.
4. “Sunshine” by Jay -Z (1997)
The future Roc Nation mogul hadn’t quite broken through to the mainstream with his acclaimed 1996 debut album, Reasonable Doubt, so on it’s follow-up, Young Hov aimed for Bad Boy-esque glossiness, which was epitomized on his irritating single that featured Babyface on the hook and a lukewarm Foxy Brown guest verse. The video became infamous for Jay’s “Joe Camel” look courtesy of weird fish-eye lens angles and tainted a lot of the reviews for what was actually one of his better ’90s albums, In My Lifetime, Vol. 1.
3. “We Made You” by Eminem (2009)
In the early 2000s, Marshall Mathers was hip-hop’s biggest star and most polarizing persona. After a string of popular, acclaimed and controversial albums, the Detroit rapper took an extended break to address his personal life and addiction issues. He returned in 2009 with the muddled Relapse album and its lead single was the kind of goofy, borderline novelty, celebrity-spoofing track that had been the first singles from most of his best albums. The problem though, was that by 2009, “Wacky Eminem” had lost his appeal and Em seemed to be going through the motions. The result? A formulaic and not-at-all funny spoof song that left his fans cold.
2. “Faces” by Run-D.M.C. (1990)
Run-D.M.C.’s fifth album is so bad, most hip-hop fans don’t even acknowledge that it happened. To casual fans, the Kings from Queens ran through 1983-1988 and then had a moderate comeback in 1993 with Down With the King. But in 1990, there was the abomination that is Back From Hell, an album that featured the late Jam-Master Jay actually rapping and the trio tackling New Jack Swing. It was all bad, and it was epitomized on this trash single that sounded like an uninspired Teddy Riley throwaway that featured a video with cameos from stars of the period like New Kids On the Block and Debbie Gibson.
1. “You Owe Me” by Nas (1999)
Nasir, Nasir, Nasir. Fans like to gloss over his late ’90s material because it features the legendary lyricist at his most desperate, and this song is a prime example. For all of his reputation as a thoughtful emcee, this Ginuwine-assisted track is one of his most callously misogynistic moments and features the rapper begging for some chart success. It turned into a moderate hit but also drew Nas’ artistic credibility into question and made him fodder for soon-to-be-rivals like Jay Z.