10 Worst Rap Songs of All Time

Throughout the ages, few genres of music have been exploited by lazy, talentless hacks as much as rap, and to prove that point we bring you the ten worst rap songs of all time.

  1. “Summer Girls” LFO.  What happens when you get a few dumb frat guys together and tell them to bust out a stream of rhyming nonsequiturs?  First they ask you what a nonsequitur is.  Then they come up with lyrics like “When you take a sip, you buzz like a hornet / Billy Shakespeare wrote a whole bunch of sonnets.”  This song will ruin your brain.
  2. “Addam’s Family (Whoomp!)” Tag Team.  Tag Team took there smash hit “Whoomp There It Is” and shoehorned in lyrics about the Addams Family, thus resulting in the lyrics, “Whoomp!  The Addam’s Family, there it is!”  If only they had applied the same tactic to other movies, we could have gotten “Whoomp!  'Schindler’s List,' there it is!” or “Whoomp!  'Ernest Scared Stupid,' there it is!”
  3. “Butterfly” Crazy Town.  Oh rap rock, you’ve taken so much from us and given so little.  If you like videos of shirtless pretty boys playing their music amid swarms of butterflies, though, then you will love the video for “Butterfly.”  Just don’t listen to the lyrics, or you will spontaneously combust.
  4. “Skat Strut" MC Skat Kat.  Someone had the brilliant idea of spinning off a cartoon character from a Paula Abdul video and giving him his own album.  Why?  One can only assume he hated humanity.  The entire album is among the worst rap you’ll ever hear, but “Skat Strut” takes the cake by virtue of having its own music video.
  5. Any Insane Clown Posse Song.  They’re tough to tell apart.  Pick one about how they’re clowns and they like to kill people and run with it.
  6. “Pumps and a Bump” Hammer.  MC Hammer has suffered several crises of identity.  For a while, he dropped the MC and became the much more hardcore Hammer.  During that time, he came out with this mind-bogglingly awful song in which he raps about his fondness for girls with… well, take a guess.
  7. “Be a Man" Macho Man Randy Savage.  Randall Savage is a man who just can’t let go of a grudge.  In this song, he lambasts his long-time arch-nemesis, Hulk Hogan.  Keep in mind this song came out in 2003, about a decade and a half past the point when Hulk Hogan could even pick him out of a lineup.
  8. “Biological Didn’t Bother” Shaquille O'Neal.  Most of Shaquille O’Neal’s oeuvre is about how awesome Shaquille O’Neal is.  On this track he deviated from that theme in order to rap about how awful Shaquille O’Neal’s biological father is.  The result?  The worst rap song among his many terribly, terrible rap songs.
  9. “K.O.B.E.” Kobe Bryant.  Not content to let Shaq be the only NBA player to thoroughly embarrass himself by branching out into rap, Kobe tried his and at it, too.  What does K.O.B.E. stand for, you ask?  It’s never quite explained.  As an added bonus, though, Kobe enlists the help of Tyra Banks to make this song even more unbearable.
  10. “Ice Ice Baby” Vanilla Ice.  Much as been said about Robert Van Winkle’s complete lack of anything resembling talent, but it bears repeating.  His career as a rapper was a cynical attempt to market hip-hop to suburban white kids who had somehow never heard of the Beastie Boys.  All of his songs are candidates for worst rap music of all time, but “Ice Ice Baby” is his most recognizable track and one he would later redo as a hardcore rock song in an attempt to reinvent himself as an even worse musician.
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