This objectively awful "rap" was a turning point in Joaquin Phoenix's career: in 2010, he told the world he planned to abandon film for a hip-hop career and a Casey Affleck-produced documentary, "I'm Still Here." The whole thing was a joke, but his attempt at rapping is all too real, with wince-worthy canned beats and his lethargic elocution.
14. Dangeruss ft. James Franco, "Hangin' Wit Da Dope Boys"
For the movie "Spring Breakers," James Franco guest-starred on "Hangin' Wit Da Dope Boys" by Florida rapper Dangeruss, who reportedly inspired Franco's character Alien. You can't really tell the actor's on the official track, but in this animated video, his limp-wristed rendition of what lyrics he remembers can't even hide behind those stunnas.
13. Kris Jenner and Nicole Richie, "Shoop"
"What's my weakness?" "Men!" No, it's rapping, as shown by this mercifully short clip of Kim Kardashian's mother and former "Surreal Life" star Nicole Richie doing severe injustice to the Salt 'N Pepa classic in sideways baseball caps. Kardashian speaks for us all as she giggles in the background while filming the video.
12. Tyra Banks Freestyles
To Tyra Banks' credit, the model gets into her freestyle, bouncing on the seat, dropping an expletive, and eventually kissing her boo Bow Wow. Her lyrics aren't the most quick-witted ("Baby I'm taken/ You know I like bacon") but she seems to pay homage to Nelly's "Ride Wit Me" with the line "Give me a kiss, Bow Wow."
11. Gwyneth Paltrow and Cameron Diaz Rap for Chelsea Handler
MC Gwyneth Paltrow and DJ Jazzy Cameron Diaz, y'all. In theory, Handler is the one being made fun of by her good friends, but the audience is all too in on the joke here as Diaz sloppily beat-boxes and Paltrow slings verse about her bedroom looking like a "lost and found" (a precursor to "Thrift Shop," perhaps?)
10. Amy Poehler, Tina Fey, and Lindsay Lohan, "Mean Girls" Rap
It's okay, Amy Poehler and Tina Fey can still do no wrong, but they got nothing on Kevin G.'s (played by Rajiv Surendra) original rap from "Mean Girls." Looking askance at the camera from under her hood while her girls bob around in the background, Poehler's clearly the beat-boxing, fake movie rap game star here.
9. John Leguizamo, "Quotes"
Long before there was Fraggle Rock or celebrities guested on Yo Gabba Gabba, John Leguizamo appeared on the 1970s children's show "The Electric Company" to rap about quotes. He doesn't make a convincing mother, but any kid who sees this will always remember to put the commas within quotation marks.
8. Hulk Hogan, "Beach Patrol"
Aside from the fact that this is a pro-wrestler with a handlebar mustache, a reality TV show, and a restaurant called Pastamania in the biggest mall in the country, Hogan is... not awful, even though he rhymes "rap-rock station" with "sticky situation" while trolling the beach for girls in need of "mouth-to-mouth resuscitation" (see what he did there?). At least he's on-beat.
7. Rodney Dangerfield, "Rappin' Rodney"
"Rappin' Rodney" is the title track off the actor and comedian's 1983 rap album, written by the same songwriters behind Kurtis Blow's "The Breaks." Dangerfield's adherence to the rhythm could use some work here, but at least his tongue is firmly in cheek ("I got a kidney pool with a kidney stone in it") and the courtroom "Saturday Night Fever"-style dancing really brings the track to life.
6. Kobe Bryant ft. Tyra Banks, "K.O.B.E."
Tyra Banks is back! For backing vocals in Kobe Bryant's eponymous entry into his short-lived rap career: after connecting with music executive Steve Soute, who showed an interest in Bryant's sparring abilities, Sony dropped him before his debut album, "Visions," was completed for a 2000 release date. He should have known that Shaq has a monopoly in the athletes-as-rappers genre.
5. Anna Kendrick, "Dongs All Over the World" and "No Diggity"
It's a tie here between a line like "Gotta catch 'em all, like sexual Pokemon" on SNL parody "Dongs All Over the World" and the sheer adorable awkwardness of Kendrick's version of Blackstreet's "No Diggity," a song that's already been covered... around the world. No matter what she does (see: "Cups") the actor has proven herself a compulsively watchable musical performer.
4. John C. Reilly and Will Ferrell, "Boats 'N Hoes"
The award for best song about seaworthy vehicles will always go to Lonely Island's "I'm On a Boat," but Ferrell and Reilly get an A for effort as Huff 'N Doback. Ferrell obviously takes his stylistic cues from the Beastie Boys, but Reilly's autotune is a bit unnecessary. Those white blazers, though, definitely are.
3. Natalie Portman, "Natalie's Rap"
Damn, girl. Natalie Portman really went all-out in this supremely aggressive, expletive-laden litany about "snorting all that yay" at Harvard. She even upstages Adam Sandberg, which is no small feat. Everyone knew she was a good actress, but with this rap she really cemented her high -- so to speak -- place in the actors-as-rappers pantheon.
2. Jimmy Fallon and Justin Timberlake, "The History of Rap"
It's almost as if Jimmy Fallon set up Brian Williams' version of "Rapper's Delight" just so he could tear it down in this medley of the evolution of rap, including classics like 2Pac's "California Love," Eminem's "The Real Slim Shady," and Soulja Boy's "You." It's worth watching the whole 20 minutes, if not for the impressive Roots-backed spectacle alone, than to watch them break it down to Sugarhill Gang's "Jump On It."
1. Terrence Howard, "It's Hard Out Here for a Pimp"
It's easy to forget Terrence Howard isn't a rapper after listening to "It's Hard Out Here for a Pimp." Penned by Three 6 Mafia, the Grammy Award-winning song from "Hustle & Flow" shows Phoenix how it's done. Too bad Howard hasn't announced any plans to get into the rap game himself.