Photos: The 25 worst rappers of all time

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Photos: The 25 worst rappers of all time

Photos: The 25 worst rappers of all time

Music critic Rob Tannenbaum laid out his list of the worst 25 rappers of all time. Click on to find out who made the list. Tom Green: The Canadian comedian rapped with the group Organized Rhymes under the name MC Bones. He also has a rap alter-ego, MC Face.

MC Skat Kat: The animated cat made his debut in the music video for Paula Abdul's 1989 song "Opposites Attract."

Chingy: The St. Louis rapper hit the scene with his 2003 hit "Right Thurr."

Joaquin Phoenix: The actor pretended to quit his day job to start a rap career for his mockumentary "I'm Still Here." In the process, he fell off a stage while trying to rhyme at a Las Vegas "show."

California rapper Too Short has managed to maintain a rapping career since the 1980s and has worked with Tupac Shakur and Jay-Z.

Will Smith: He's known these days as an actor, but Smith started out as the rapper Fresh Prince, along with his pal DJ Jazzy Jeff. His more recent rap career -- including the album "Willenium" -- has taken its lumps from critics and rap purists.

Pro Athletes, Post-1985: Including the 1985 Chicago Bears with the "Super Bowl Shuffle" and the Lakers' Ron Artest.

Soulja Boy: The rapper, who grew up in Georgia, was taken to task for his song "Pretty Boy Swag."

Weed carriers: That is, sidekicks for rappers who are likely only around to provide drugs. Examples: Eminem's pal D12 (pictured) and Nelly's the St. Lunatics.

Brian Wilson: The brains behind the Beach Boys recorded a rap track for the unreleased 1990 album "Sweet Insanity."

Madonna: The pop princess rapped about her charmed life in 2003's "American Life."

David Bowie and Mickey Rourke: The pop singer and the actor joined forces on the 1987 song "Shining Star (Makin' My Love)."

Master P: The New Orleans rapper seems to have had better success with his career as a producer.

Prince: The singer rapped stiffly on several albums in the 1990s, including "My Name is Prince."

Eazy-E: The rapper often played sidekick to Ice Cube, who wrote most of his best lyrics.

The two guys in the black eyed peas who aren't will.i.am: That would be apl.de.ap and Taboo.

Pitbull: Tannenbaum calls the Puerto Rican rapper "a Cuban-American Vanilla Ice."

MC Hammer: The "U Can't Touch This Rapper" hasn't exactly left a shining legacy.

Everyone from England, ever: With the exception of The Streets rapper Mike Skinner.

Puff Daddy: Or Diddy, or Sean Combs, depending on the day, has, like Master P, more success as a producer and nurturing other talent than as a rapper.

Kevin Federline: The ex-backup dancer and Britney Spears' ex tried his hand at the rap game, but didn't make much of an impression.

Chet Haze: aka Chester Hanks, aka son of Oscar-winning actor Tom Hanks and actress Rita Wilson (pictured) hit the scene in 2010 with a series of YouTube videos.

Spencer Pratt: The television personality, who acheived a certain level of fame from his appearances on the MTV show "The Hills" and his relationship with Heidi Montag, made his rap debut on "I'm a Celebrity."

Vanilla Ice: aka Robert Van Winkle, was "history's first truly awful rapper," according to Tannenbaum. Since his "Ice Ice Baby" fame has fizzled, he's recorded a rap album and dabbled in reality television.

Insane Clown Posse: The be-make-uped duo of Violent J and Shaggy 2 Dope make millions each year from albums, DVDs, comic books and a music festival.

1/25

Music critic Rob Tannenbaum laid out his list of the worst 25 rappers of all time. Click on to find out who made the list. Tom Green: The Canadian comedian rapped with the group Organized Rhymes under the name MC Bones. He also has a rap alter-ego, MC Face.

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