Which Oscar-Winning Actor Is The Best Rapper? A Ranking

Kevin Winter/Getty Images

Which Oscar-Winning Actor Is The Best Rapper? A Ranking

Kevin Winter/Getty Images

Look, there are things happening in rap music right now. I could write a column about the new R.A.P. Ferreira album, the new Big Yavo album, or the new Your Old Droog album. I could write about the tragic death of Young Dolph, or, for that matter, about the tragic death of rap-adjacent designer Virgil Abloh. I don’t want to do any of those things. I got my booster shot last night, so I feel like ass, and I don’t want to think too deeply about anything. So let’s get goofy with it.

Right now, Will Smith is the odds-on favorite to win the Oscar for Best Actor next year. Smith has been nominated twice in the past, for Ali and The Pursuit Of Happyness. He’s also been one of the planet’s most famous movie stars for nearly 30 years. This year’s nominations aren’t out yet, but Smith is a lock to at least get a nod for his work as Richard Williams, father of Venus and Serena, in King Richard. That movie came out last week, and it’s pretty good. I watched it with my daughter, and it’s a very watch-it-with-your-daughter type of film. Smith is great in it. I haven’t seen most of this year’s other highly touted contenders, but right now, I’m rooting for Smith.

Part of the reason that I’m rooting for Will Smith is that Will Smith was my first favorite rapper. He’s The DJ, I’m The Rapper was a hell of a gateway drug, and it’s still probably the main reason why I love that guy. Within a decade after that album, Smith made a couple of unlikely leaps — first to sitcom lead, then to dominant movie star. Already, Smith is in a very small company of former rappers who have been nominated for Oscars as actors. (I’m pretty sure that the only other two are Mark Wahlberg and Queen Latifah, the latter of whom gets extra props for being nominated under her rap name. Mary J. Blige is the queen of hip-hop soul, but I don’t think it makes sense to talk about her as a former rapper.) Thus far, nobody who got famous rapping has ever taken home the gold. If Will Smith wins it, he’ll be the first, and he’ll vault right to the top of the list of best rappers who are also Oscar-winning actors.

In anticipation of Smith’s possible win, I did an extensive scientific survey of which Oscar winners have tried their hands at rapping. (I Googled all of their names and the word “rapping.”) This ranking doesn’t include the rappers who have won the award for Best Original Song. (That list includes Eminem, Common, Juicy J, DJ Paul, and Frayser Boy.) It also doesn’t cover Best Director, which means we won’t have to deal with Warren Beatty in Bulworth.

Bulworth or no Bulworth, most of this list comes from deep in the cringe-zone. It doesn’t include Lip-Sync Battle performances or videos of actors rapping along with songs like that one clip of Leonardo DiCaprio doing “Scenario” at the club. It doesn’t factor in whether or not the actors have rap songs named after them. (Fun fact: Both Migos and Brother Ali have songs called “Forest Whitaker,” but Forest Whitaker has never, as far as I know, done any rapping.) Sadly, this list does include actors rapping as a stupid human trick on late-night talk shows. There has been a lot of that.

Some further clarifications: Morgan Freeman hosted 21 Savage’s Savage Mode 2, and his between-song interstitials sounded a bit like Big Rube, but that doesn’t count as rapping. Eddie Redmayne has never rapped, despite having a last name that looks a lot like “Redman.” (Bless Redmayne for fending off what must’ve been a million Jimmy Fallon/James Corden invitations to put him in a skit with Redman.) Also, there’s apparently a rapper named Tommy Lee Jones, who has a song with Vanilla Ice. But unless this is a miraculous actor’s transformation, it’s not that Tommy Lee Jones. Nobody could sanction that buffoonery.

With that in mind, here we go, worst to best.

27. Joaquin Phoenix
In 2010, Joaquin Phoenix and director Casey Affleck came out with I’m Still Here, a sort of prank mockumentary about Phoenix leaving behind his life as an actor to become a rapper. (Affleck got sued for sexually harassing women on the film’s set. He’s also an Oscar winner, but I don’t think he does any rapping in the movie, so I’m not including him.) I’ve never seen I’m Still Here, and I find this whole exercise to be utterly bankrupt at the most basic level. All the videos I’ve seen of Joaquin Phoenix rapping make me want to climb out of my skin. He’s dead last for a reason.

26. Sandra Bullock
It’s never any fun when famous white people go on talk shows and pull the whole “I know all the words to a rap song” trick. This isn’t Sandra Bullock’s fault; it’s the late-night industrial complex continuing to shovel goober shit into our collective face. Nonetheless, Sandra Bullock’s “Rapper’s Delight” is the worst of these because (1) everyone knows the words to that song and (2) she looks utterly humiliated. This is rough watching.

25. Gwyneth Paltrow
These British talk show hosts sure love it when white American actresses rap, don’t they? Gwyneth Paltrow doing N.W.A is only marginally better than Sandra Bullock doing the Sugarhill Gang because Paltrow at least seems to enjoy herself. Still: Eek.

24. Meryl Streep
I will never, ever watch The Prom, the Netflix musical about Broadway stars going to a small-town high-school dance or whatever. But the cheesed-out self-empowerment soundtrack song “Wear Your Crown” has a Meryl Streep rap verse. This is a thing that should not be. The “just go high like Michelle Obama” line may have actually killed me. I might be writing the rest of this column from beyond the grave.

23. Rami Malek
In the 2013 indie drama Short Term 12, Freddie Mercury rapped exactly one bar. It’s bad, but it’s supposed to be bad, and it’s a cute little character moment. (If LaKeith Stanfield, the other guy rapping in that scene, had won Best Supporting Actor earlier this year, he’d be a lot higher on this list.)

22. Robin Williams
Given Robin Williams’ well-documented fondness for doing ethnic accents and his total lack of restraint in the field of broad comedy, it’s frankly incredible that Williams didn’t do a whole lot more joke-rapping in his career. Thank god. Williams’ most prominent rap performance was in the 1992 animated film FernGully: The Last Rainforest, where he played a bat named Batty. His one song about being a bat is definitely bad, but it’s nowhere near as offensive as it could’ve been.

21. Anne Hathaway
“It’s in the style of Lil Wayne.” No. Absolutely not. Unacceptable.

20. Robert De Niro
In 2016’s Bad Grandpa, Travis Bickle does about 30 second of Ice Cube’s “It Was A Good Day.” He says the N-word. It was not a good day.

19. Judi Dench
This video, in which grime overlord Lethal Bizzle attempts to teach Dame Judi Dench how to rap, is clumsy and embarrassing and at least a tiny bit charming. The rapping is awful, but she’s only just learning, and she’s not being a weirdo about it. She seems fun.

18. Whoopi Goldberg
In 1993’s Sister Act 2: Back In The Habit, Whoopi Goldberg delivers a couple of lines, and they’re deeply grating. But it’s not her fault that she had to rap after a pre-megafame Lauryn Hill. Somebody did Whoopi dirty there.

17. Joe Pesci
On his 1998 song “Wise Guy,” Joe Pesci raps big-willie shit over a Blondie sample. This wasn’t something that Pesci did for a movie role; he released this song of his own volition. I would love to know more about the series of decisions that led to this. On “Wise Guy,” Pesci is more on-beat than you might expect, and I sort of believe what he’s saying. It’s terrible, of course, but I’m vaguely happy that it exists.

16. Tim Robbins
This list managed to avoid all things Bulworth, but we are unfortunately forced to engage with Tim Robbins’ 1992 political satire Bob Roberts, which also has its auteur rapping. In this case, it’s our boy Andy Dufresne doing overworked lines about the economy in an extended riff on Bob Dylan’s “Subterranean Homesick Blues.” Baffling.

15. Chris Cooper
In the 2011 Muppets movie, Chris Cooper plays a greedy corporate exec, and he has a rap song about being a greedy corporate exec. This is amusing on paper, but it would probably work better if Chris Cooper had ever listened to a single rap song in his entire life.

14. Helen Mirren
We should honor Helen Mirren for being game enough to do a televised rap battle with James Corden, and we should also condemn James Corden for convincing Helen Mirren to do a televised rap battle. Mirren can’t rap, but through sheer charisma, she elevates this beyond the Wedding Singer bit where the old lady does “Rapper’s Delight.”

13. Jennifer Hudson
Look, nobody wanted back-to-back James Corden rap battles, but that’s just the way this shit shook out. Jennifer Hudson clearly knows what rap music is, so she’s ahead of most of these fools.

12. Al Pacino
Thanks to Scarface, Pacino has probably been namechecked on more rap songs than any other Oscar winner, but that doesn’t help his standing on this list. Instead, Pacino is here because he was willing to play himself in the notoriously terrible Adam Sandler vehicle Jack And Jill and because he put some serious energy into this fake commercial where he raps about donuts. He truly commits to the bit, and the result is mesmerizing.

11. Sam Rockwell
On a bonus feature from the Galaxy Quest DVD, Sam Rockwell, Sigourney Weaver, and Daryl Mitchell all rap for some reason. It’s deeply grating, but Rockwell comes out of it intact because he only raps a couple of lines and because he seems like he’s profoundly drunk. Sigourney Weaver absolutely should’ve won an Oscar by now, but if she had, she would not have done well on this list.

10. Adrien Brody
Adrien Brody looks like a guy who would make rap music in his spare time, and that’s exactly what he is. But Brody mostly makes beats; he’s talked in interviews about getting Raekwon and NORE to freestyle over his tracks. The only evidence I’ve found of Brody actually rapping his this weird, muddy video where he’s with a Russian guy who looks like Drake. It’s OK?

9. Brie Larson
Does this even count? Larson played Lesley Gore in an SNL sketch once, and she sang a few lines from Big Sean’s “Dance (Ass).” Maybe that’s not rapping? But it sounds pretty good? I don’t even know, man. I want to go to bed.

8. Marion Cotillard
What the fuck is even happening here? And why does it go so hard?

7. Jean Dujardin
Why did the artist from The Artist show up on a song with French rappers Bigflo & Oli? And why is he wearing a blonde wig in the video? I don’t speak French or understand French culture, so this is all terribly mysterious, but I don’t hate it. (This song, from the soundtrack of something called Brice 3, was a #23 hit in France and a #18 hit in Belgium. I guess they respect artists over there.)

6. Natalie Portman
The entire comic premise of “look at this refined white person rapping” needs to be locked in a trunk and banished to the bottom of the ocean. But as long as this shit continues to exist, Natalie Portman’s two Lonely Island videos are among the best examples of the form. It’s nice that Nine’s 1995 banger “Whutcha Want” lives on in some form.

5. Jamie Foxx
Jamie Foxx has a whole successful, lucrative side hustle as an R&B singer, and he’s collaborated with a whole lot of rappers over the years. He sang the hooks of two of Kanye West’s three #1 hits, and he also wrote and co-produced “100 Black Coffins,” the Rick Ross song from the Django Unchained soundtrack. I really like that song. Foxx hasn’t done a whole lot of actual rapping, but this live freestyle with Common proves that he knows how to do it. (We’re still waiting on that Common/Jamie Foxx album.) Foxx might be the only rapper on this list to rap about winning an Oscar, and the trick of breaking into “Blame It” mid-verse is cheap but effective.

4. Lupita Nyong’o
Hey look, it’s the most beautiful woman on the planet freestyling over the “NY State Of Mind” beat in the backseat of a car. I’m not saying no to this. (I could’ve put a Jimmy Fallon video in here, but you’ve endured enough of that foolishness by now.)

3. Tom Hanks
This is not about Chet Hanks, Tom’s wayward child. White boy summer is over. Instead, it’s about “City Of Crime,” the strange and catchy Beastie Boys bite that Hanks and Dan Aykroyd recorded for the soundtrack of 1987’s Dragnet. I have loved that song since I was eight years old, and Hanks’ genuinely unhinged performance is one of the best things about it.

2. Daniel Kaluuya
On an early episode of Skins, a teenage Daniel Kaluuya jumped onstage and delivered a perfectly credible grime track. Kaluuya co-wrote the song, and years later, he still remembered his lyrics.

Also, in the best scene of 2018’s Widows, Kaluuya delivered a bit of strong, memorable rap criticism. RIP to the Cool Kids.

1. Mahershala Ali
Honestly, it’s not close. Before his acting career took off, two-time winner Mahershala Ali made a respectable attempt at carving out an underground rap career, linking up with the great Bay Area crew Hieroglyphics and releasing a 2007 album under the name Prince Ali. (Great rap name.) His shit is genuinely hard, and if he ever wanted to return to rapping, he could do some damage. I want Mahershala Ali to rap more, and that’s not something I’m going to say about anyone else on this list.

FURIOUS FIVE

1. R.A.P. Ferreira – “Humboldt Park Jibaritos”
R.A.P. Ferreira just released a whole album of floaty, impeccably worded head-blown boom-bap, and it’s great. This song is my favorite, and I can’t tell if it’s because of the DJ Shadow reference or the free-floating sax loop or what. It’s just pretty.

2. Sada Baby – “CJ”
For the past few years, we’ve gotten hundreds of great Sada Baby tracks. We’ve been spoiled. At this point, I expect workmanlike excellence from Sada. Every once in a while, though, he gets so much fire in his belly that he blows past that and into some berserker-rage fugue state.

3. Trapland Pat – “4 & A Baby”
Trapland Pat is a young South Florida rapper who looks and moves like the current generation of young South Floria rappers, but he’s making shit that would’ve sounded just as good in 1996. That’s quite a trick.

4. Fly Anakin – “Ghost” (Feat. Nickelus F)
Things are happening in Richmond. Pay attention.

5. Defcee & Messiah Muzik – “Shortcuts” (Feat. PremRock & Armand Hammer)
Muddy and fractured underground rap never left, but right about now, it sounds like it’s coming back anyway.

IT WAS ALL GOOD JUST A WEEK AGO

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