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Top 10 Celebrity Raps

VO: Rebecca Brayton
Script written by Q.V. Hough These are the wealthy purveyors of street-wise sensibilities. Join WatchMojo.com as we count down our picks for the Top 10 Celebrity Raps. For this list, we're focusing on atypical rapping celebrities, and basing our choices on a mix of their skills, popularity and the entertainment value provided. Special thanks to our user Felix_B for submitting the idea on our Interactive Suggestion Tool at WatchMojo.comsuggest
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Top 10 Celebrity Raps


These are the wealthy purveyors of street-wise sensibilities. Join WatchMojo.com as we count down our picks for the Top 10 Celebrity Raps.

For this list, we’re focusing on atypical rapping celebrities, and basing our choices on a mix of their skills, popularity and the entertainment value provided. This also means someone like WWE star John Cena has been excluded, as he’s been known to drop a rhyme or two over the years.

#10: “It’s Hard Out Here for a Pimp”
DJay feat. Shug

Playing a Memphis pimp turned poet, Terrence Howard produced a critically acclaimed performance in Craig Brewer’s indie drama, largely due to his natural flow in the studio. Rapping “It’s Hard Out Here for a Pimp,” Howard’s unique voice lent the necessary grit at a pivotal moment in the film as Djay makes the transition from street hustler to recording artist. The song itself was originally written and recorded by Three 6 Mafia, who actually won Best Original Song at the Academy Awards for it, but it was Howard’s rendition that amped up the plot for one of the year’s most surprising films.

#9: “Thug Story”
Taylor Swift feat. T-Pain

Back in 2009, Taylor Swift won Video of the Year at the CMT Music Awards for her crossover hit “Love Story.” But she also dropped a bomb on older generations by teaming up with T-Pain for a hip-hop REMIX entitled “Thug Story.” This was the moment when the pop culture persona of “T-Swizzle” was born, however it was clear that Taylor was no rookie to the rap game after years upon years of performing to a mirror. Complemented by the auto-tuned vocals of Mr. Pain, she unleashed the fury and conveyed all the inner turmoil that comes from living with your parents and having a record deal.

#8: “Rappin’ Rodney”
Rodney Dangerfield

In the early ‘80s, white America wasn’t necessarily in touch with the layered artistry of hip-hop, and so, an elderly, white comedian decided to introduce the art form to a mainstream audience. Enlisting the song-writing team behind Kurtis Blow’s “The Breaks,” Rodney Dangerfield broke down the basics of being old, and well, broken down. All joking aside, the legendary comic held his own, and while “Rappin’ Rodney” was indeed a novelty track, nobody expected a 60-something-year-old comedian to embrace the genre with such... gusto. Word.

#7: “City of Crime”
Tom Hanks & Dan Aykroyd

Years before Andy Samberg and Chris Parnell went hardcore with “Lazy Sunday,” another “Saturday Night Live” star joined forces with a future box office sensation for “City of Crime,” a hard-hitting lyrical production unfortunately complemented by an embarrassing dance routine. But hey, that’s a crucial element for any white man rap parody, and both Tom Hanks and Dan Aykroyd saved the “Dragnet” production with a commitment to their characters and a Beastie Boys-inspired aesthetic. The rhymes may seem lame today; however back in 1987, “City of Crime” was pure fire.

#6: “Freestyle Rapping”
Shia LaBeouf

Alright: we’ve all wanted to punch Shia LaBeouf at one time or another, but you’ve got to give the guy some credit - he keeps the “artistic” dial cranked at all times. Sure, maybe Shia wasn’t even spitting his own lyrics during his 2015 park freestyle, and maybe the whole thing was plagiarized, but it’s evident that he’s made significant progress since his innocent appearance years before on “The Late Late Show with Craig Kilborn.” He may look like a modern day version of a drunken Davey Crockett, but we gotta give him props for rhyming “Galileo” with “mashed potatoes.” This guy was cookin’.

#5: “Boats ‘N Hoes”
Will Ferrell & John C. Reilly

In arguably one of the most underrated comedies of recent years, a couple of socially awkward step-brothers lived out their fantasies through a bootyful production entitled “Boats ‘N Hoes.” Understanding that it was no longer cute for 40-year-old white men to simply act like the Beastie Boys, John C. Reilly and Will Ferrell went all in and insightfully articulated the sexual dreams of their characters. Just a couple of pirates of the sea, Brennan Huff and Dale Doback came to life through the natural charm of the actors with this tune.

#4: “Treat Your Mother Right”
Mr. T

By 1984, A-Team-mania was in full effect, so naturally, executives had the show’s only black guy release a rap novelty song - even if he was the one man who probably shouldn’t have been rapping at all. Finger on the pulse, people. Finger. On. The Pulse. Somehow it worked – kinda - it's hard to disagree with the song's message, even if the questionable music video was flat-out creepy. What sold the entire production, however, was Mr. T’s conviction and growling vocals, despite the rather basic collection of rhymes. It's just too bad T didn't drop a joint with Dwight Schultz, that woulda been tight!

#3: “History of Rap”
Jimmy Fallon & Justin Timberlake

They both hit the big-time around the same time in the late ‘90s, and over the years, Jimmy Fallon and Justin Timberlake have become standout entertainers in a world of fame-hungry reality stars. And when they introduced the “History of Rap” in 2010, they combined their knowledge of the genre with their vast experience in performance art. In other words, they killed it, both with their vocals and stage presence while ushering in a new era for white men who genuinely understand the essentials of hip-hop.

#2: “Alphabet Aerobics”
Daniel Radcliffe

While Jimmy Fallon was born and raised in New York, the home of hip-hop culture, Harry Potter himself grew up across the pond. In this clip, it’s easy to recognize the utter fascination of the “Tonight Show” host as Daniel Radcliffe explains his appreciation for rap music. Like a true performer, the actor loses the jacket, grabs the mic and unleashes a surprisingly impressive rendition of Blackalicious’ “Alphabet Aerobics.” Sure, it would have been more genuine had he retained his own accent, but regardless, Radcliffe’s lyrical proficiency improved with every second.

Before we unveil our top pick, here are a few honorable mentions.
- “Lil Wayne-Style Paparazzi Rap”’
Anne Hathaway
- “Scene to Rap”
Stephen Colbert
- “Freak of the Week”
DJ Polo feat. Ron Jeremy
- “Wise Guy”
Joe Pesci

#1: “Natalie’s Rap”
The Lonely Island feat. Natalie Portman & Chris Parnell

Since her 1994 film debut, Natalie Portman has emerged as one of cinema’s most lovable sweethearts. Incidentally, her shaved-head performance in 2006’s “V for Vendetta” caused a stir, as did the SNL digital short in which she went buckwild for a fictional parody that preceded years of “good girl” celebrity meltdowns. Shot in poignant black and white and fueled by Portman’s X-rated lyrics, “Natalie’s Rap” takes the cake on a variety of levels, largely in part to the pure lunacy and shock effect that it includes.

Do you agree with our list? What is your favorite celebrity rap? For more mind-blowing Top 10s published daily, be sure to subscribe to WatchMojo.com.
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