The 25 Funniest Rappers of All Time

One of the greatest feelings in hip-hop is to be in on the jokes. Many of our favorite MCs are funny in their own ways, delivering lines that are twisted, dark, satirical, horny, shocking, or just flat-out ridiculous. The absolute best of the best can crack jokes without sacrificing their abilities on the mic or making a mockery of the genre. And it’s not enough to just be funny—the masters create songs where the laughs are just as essential as the beat and the flow.

Comedy can sometimes also feel like the only way to deal with the world’s atrocities and injustices. In rap there’s so much humor sourced from topics that shouldn’t be funny: Violence, death, relationship turmoil, neighborhood ruin, police brutality, and government neglect can be punctured, if only for a moment, with a perfectly sharp bar.

Funny rappers come in many different forms. There are the goofballs, the instigators, the punchline wizards, the outright maniacs, the ones who may or may not be doing a bit, and more. Here are our favorites, in alphabetical order.

2 Chainz

2 Chainz has the delivery of a stand-up comic—rarely in a rush, he lets punchlines breathe for a second so they really hit. The Atlanta vet is constantly dreaming up lyrics that feel like absurd twists on everyday rap flexes. Instead of bluntly saying he’s turned on, he raps, “My dick so hard it make the metal detector go off.” Some of his lines turn into cartoon strips the moment they leave his mouth: “My bathtub the size of swimming pools/Backstroke to my children room.” Really, his bars are best when they’re nonsensical, or when he’s just playing with words for the hell of it. If you’ve ever been in a room full of people happily rapping along with a couplet like, “Rest in peace to all the soldiers that died in the service/I dived in her cervix,” you know exactly what I mean. –Alphonse Pierre

Funniest song: “Where U Been?”

Biz Markie

Biz Markie always understood how vulnerability could make for a good laugh. The most famous example is his trademark 1989 single “Just a Friend,” which takes Freddie Scott’s R&B hit “(You) Got What I Need” and turns it into a tale of dejected love for the ages. But Biz was always willing to go the extra mile to be his wacky self—with no reservations—in all of his music. His beatboxing and vocal scratches gives his vintage hip-hop jam “Make the Music With Your Mouth, Biz” a silly, approachable air that’s hard to resist. Whether he’s calling out producers for their “doo-doo” beats or rapping about the virtues of his favorite breakfast cereal, there’s always a reason to smile, chuckle, or belly laugh your way through a Biz Markie song. –Dylan Green

Funniest song: “Just a Friend”

Cam’ron

Judging by his raps, Cam’ron has never felt insecure a day in his life. His lyrics are all extreme gusto and charisma. The Harlem heavyweight is the type of rapper who makes complete bullshit sound like it should be scripture, often causing you to spit out your water in the process. He’s so casual about his unruly tongue twisters and depraved words of wisdom that you’re unsure if he’s even aware how wild they are. “I advise you to step, son/’Fore I fuck your moms, make you my stepson,” is how he kicks off his classic 2002 album Come Home With Me.

Sometimes he gets twisted pleasure out of just clowning others like a schoolyard bully: On his iconic Jay-Z diss “You Gotta Love It,” he gets on Hov for being born in the ’60s, wearing open-toe sandals, and being a fraud. “How’s the King of New York rocking sandals with jeans and he 42 years old?” Cam pontificates, as if he’s going for the jugular in a presidential debate. He’s a natural comedian, funny without trying that hard to be—and if you accuse him of taking things too far, he’ll just go even harder. –AP

Funniest song: “You Gotta Love It”

Cardi B

Like Rosie Perez in White Men Can’t Jump, Cardi B’s unmistakeable New York City accent makes every word she raps sound both furious and hilarious. On “Cheap Ass Weave,” the natural disgust in her voice makes it sound less like she’s making fun of some girl’s crumbling, bargain-bin sew-in and more like she’s truly disturbed by it. She can also come up with extremely visual scenarios that work as unforgettable sight gags. Like on “She Bad,” where her outfit even has the preacher profusely sweating in church; or the description of her hair on “Tomorrow 2”: “Long-ass weave, it be ticklin’ my ass crack.” 

Her voice is probably best suited for disrespect, though. Bars like, “Get it from my mama, and you don’t know where yo’ daddy at” and, “Call your mama phone, let her know that she raised a bitch” wouldn’t sound as good if they were rapped by anyone else but Cardi. I bet she dominated the lunchroom roast sessions back in the day. –AP

Funniest song: “Tomorrow 2”

CupcakKe

“I thought I came but I peed on the dick” is easily one of the wildest opening lines to any song ever. But for CupcakKe, it’s also par for the course. Taking a page from rappers like Lil’ Kim and Nicki Minaj, the Chicago rapper’s bars are more than just provocative, with enough detail, innuendo, and sheer what-the-fuck-ness to make a porn star blush. On “CPR,” she finds dozens of ways to talk dirty over a tropical beat mixed with moans and pops (some favorites: “I got three holes for it like a pretzel,” “Licking on that penis like a letter when I seal it,” “Dick twisting in my stomach like food poisoning”). The confidence with which she delivers her punchlines has made her one of the most fun MCs to hit the scene in the last decade, whether she’s rapping about reading Goodnight Moon while “ridin’ on that dick” or giving someone blue balls like a Smurf. –DG

Funniest song: “Cartoons”

Danny Brown

I can’t think about Danny Brown without first thinking about the smell of Cool Ranch Doritos. That’s how much the last bar of “Monopoly”—where he compares “stank pussy” to the snack food’s signature aroma—has stuck with me since it initially slapped me across the face 12 years ago. Though he’s developed a reputation as a storyteller unafraid to shed light on addiction and depression, Danny is primarily a punchline rapper in the strictest sense. His metaphors are succinct and detail-oriented, pulling from references across the spectrum, from old-school rap classics to Elvis dying on the toilet. And even when he isn’t joking, his squawk of a voice is enough to give any threat, thought, or feeling an extra giggle-inducing layer. –DG

Funniest song: “Monopoly”

Fabo

Snap music trailblazer Fabo’s combustible, chaotic, and often improvisatory rapping style was born out of growing up on soulful legends like James Brown, Michael Jackson, and Curtis Mayfield. As a member of the Atlanta group D4L, he pushed those influences to the brink with a few of the most batshit musical moments in hip-hop history. Think of his vocal acrobatics on “Scotty,” where he’s panting and hollering and chanting while capturing the feeling of being way too high better than anyone else. His verse on D4L’s landmark hit “Laffy Taffy” is unhinged, of course, but it’s the brief second where he channels New Edition and wails “Candy Girl” for no reason at all that makes it all click into place.

But his funniest moment comes in the final seconds of “Tattoo,” where he sounds possessed, or at least like he’s on his knees in the rain begging for love while he screams the name “Barbaraaaaaa!” He recently told The New York Times that when people would ask, “Who is Barbara!?” he would say, “That’s what I heard in the track, bro.” Forever so random. –AP

Funniest song: “Tattoo”

Ghostface Killah

Standing out in a pack of rappers named after comic book and kung-fu film characters is a tall order, but Ghostface Killah did just that with humor and menace. He once famously boiled his style down to finding “official beats” and saying “some fly shit over them,” and that has translated in ways both direct and abstract. Though he isn’t a punchline rapper per se, his yawp of a New York accent makes every word feel both serious and casual at the same time. The bars get even funnier when they dip into outright surrealism, like when he boasts about eating “seasoned giraffe ribs” on “Nutmeg,” from 2000’s Supreme Clientele, or how, on 2006’s “R.A.G.U.,” he tells a story of a friend who once shot himself in the groin (“‘Shit, I put one in my balls, what the fuck y’all looking at me for?!/Call the police, do something!’”). Ghost’s sincerity makes every situation funnier—he’s like your favorite uncle who’s always got a story, even if your mother is side-eyeing him the whole time. –DG

Funniest song: “Nutmeg”

Kevin Gates

One of the most brutally honest storytellers of his generation, Kevin Gates makes emotional, melodic music in the lineage of other Deep South rappers like Boosie and Lil Phat. He’s also our poet laureate of sucking toes (“I was rubbing on your titty/With your toes in my mouth”), eating pussy (“Eat the pussy from the back and I don’t give a fuck who looking”), and getting head (“I’m in the Vette gettin’ neck from a giraffe, and I pray to God that we don’t crash”). He has never heard of a filter.

There’s no sign he’s joking, either. Many of these lyrics are said in the same I’m-going-through-some-shit cadence that he uses to sing-rap about pain and struggling. On the opening line of “Wild Ride” he sings, “Would I be wrong, wanna fuck you with one of my niggas?” like he’s baring his soul. Or on the hook of “Luv Bug,” when he sweetly croons, “I’m stickin’ my tongue all in her ass, don’t budge” as if he’s talking about bringing his girl flowers for her birthday. –AP

Funniest song: “Wild Ride”

Kool Keith

“Stream-of-consciousness” doesn’t do Kool Keith’s style justice—he raps like a walking tab of acid. As a member of the foundational golden era group Ultramagnetic MC’s, the Bronx-born rapper always played fast and loose with rhythm. But he really began to embrace the weird and hilarious after going solo, adopting a series of alter egos, each one stranger than the last. On projects like 1996’s Dr. Octagonecologyst or 1999’s Black Elvis/Lost In Space, he spun sci-fi and horrorcore tales into bouts of surrealist camp. He can take a completely nonsensical line like, “Checking out doo-doo on flame pits” and make it sound like a cogent metaphor, or make something direct like, “Y’all front on BET with slum gold, drivin’ rentals” and make it sound alien. Beyond the scatalogical punchlines, what makes Keith funny is his unpredictable approach. You never know what version of him you’ll get, and that misdirection is the setup for one of the oddest and most amusing runs in rap history. –DG

Funniest song: “I’m Destructive”

Lil B

No rapper will ever troll like Lil B trolls. Like a rap-world Eric Andre, he knows how to push even his most based followers to their limits with bits that seemingly have no end. In his 2010s prime, he would dive into unplaceable accent work, or just shout the name of random celebrities for no real reason, or cruise through with directionless freestyle raps that led to chants of “Based God fucked my bitches.” For all of his one-of-one eccentricities, Lil B is a real student of the game—taking notes on everyone from Soulja Boy to Gucci Mane to Wayne to Bay Area legends like E-40 and Keak Da Sneak—making him able to deconstruct rap songs in a particularly shrewd way. His diss tracks, specifically, fall somewhere between parody and completely deadass, a middle ground that is hard to touch. My favorites include “T Shirts and Buddens,” where he rags on Joe Budden for being old and a pervert, and “Fuck KD,” the Kevin Durant hate track that may have single handedly changed the trajectory of NBA history. –AP

Funniest song: “Ellen Degeneres”

Lil Wayne

It’s scary to think about all the brilliantly random punchlines Lil Wayne rapped into a microphone one time and then never thought about again. (In an interview this year, he even mentioned hardly remembering Tha Carter III, his most popular album.) During his late-2000s mixtape run, he seemed to be having an out-of-body experience on a weekly (daily?!) basis, rattling off sharp observations and croaky one-liners at a relentless rate. Many of the best were spit-take riffs on the idea that he is, simply, the shit (see: “I’m the hardest shit, go in your ass and search” and the classic, “Dear Mr. Toilet, I’m the shit”), or just extremely high; when he rapped, “I’m so motherfuckin’ high, I can eat a star,” you could practically see the celestial chomp marks. The only way to reasonably respond is to hit one of his signature chuckles. –AP

Funniest song: “Gangsta and Pimps”

LL Cool J

LL Cool J’s music-video antics have been well-documented, from emerging out of a body of water in jeans strapped with an enormous belt buckle to slobbering on an ice cream cone with honey as an act of romance. His lick-lipping, often-shirtless thirst trapping makes for some odd moments that happen to be very funny (whether or not that was his intention).

He’s just as strange on the mic: a goofy and criminally horny rapper who can still spit circles around anyone. On 1993’s “Pink Cookies in a Plastic Bag Getting Crushed by Buildings,” he dives into the “act of makin’ love,” which, in true LL fashion, includes scenarios like, “Come to my house/Turn on the lights, and see me on the couch” (which sounds more horrifying than sexy) and, “Rub ya down with warm iced tea” (did he run out of lotion?!). He’s just as foolish in storytelling form. Just listen to 1989’s “Big Ole Butt,” where each verse tells a different tale of him cheating on his girl because he loses all motor skills when faced with large booties. Even on megahits, he’s so dramatic and weird: “Kiss you slow and stare in your eyes,” he raps on “Luv U Better,” as if his idea of love is straight out of a Nicholas Sparks novel. LL is rap’s most irrational lover boy. –AP

Funniest song: “Backseat”

Ludacris

I will always think of Ludacris with either cartoonishly inflated biceps (as seen in the “Get Back” video) or a gargantuan bobble head (like in the “Rollout (My Business)” clip). In the early 2000s, it seemed like a month didn’t go by without a ridiculous Ludacris music video that perfectly matched the madcap energy of his bold-font bars and explosive flow.

Luda has punchlines for days; they can be vivid, offensive, sourced from pop culture, or just flat out loony. The best of them check many of these boxes all at once. On “Hip Hop Quotables,” he’s smoking weed with Bill Clinton, going on blind dates with actual blind people, quoting South Park, and claiming that “They made the mold of the penis enlarger off me.” Then there are all of the spots where he dreams of having sex on “What’s Your Fantasy”: a barn, on the back of a horse, on an Escalade’s roof, on the 50-yard line of the Georgia dome. The comedic creativity is boundless. –AP

Funniest song: “What’s Your Fantasy”

MF DOOM

A cynic by nature, MF DOOM rapped like a worldly smart-alec, capable of being dense and direct at the same time. Bars poking fun at rappers who snitch on themselves sit next to nursery-rhyme interpolations and samples ripped from Fantastic Four cassette tapes. He dedicated entire songs to fake personae based on secondary Godzilla characters and to navigating a date with a woman who has bad breath. The mystery surrounding DOOM as a person always added a layer of intrigue to his artistry, but his ability to find the absurd anywhere he looked is one of the main reasons why his music continues to thrive. –DG

Funniest song: “Figaro”

Missy Elliott

One of my earliest rap memories is watching the video for Missy Elliott’s “The Rain (Supa Dupa Fly)” and wondering why she looked like a burnt marshmallow. But there she was, gyrating in front of a fisheye lens and cooing to a lover in the Hype Williams-directed video, as if she were the star of her own surreal sci-fi romantic comedy.

The Virginia rapper-producer has plenty of chuckle-worthy lines in her songs, but most of what makes her funny is in her delivery, general exuberance, and peerless visual creativity. The way she flows through her first verse on “Work It” and ends most bars with “‘ya” makes plain statements like, “Give me all your numbers so I can phone ya” or babbles like “ra-ta-ta-ta-ta-ta-ta-ta-ta-ta” land with a carefree lightness. And, of course, she says these things in the video while spinning on her head like the Tasmanian Devil with a taste for Adidas tracksuits. Missy is playful, never one to shy away from the absurd, whether that’s flying through space dressed up like a ghetto fabulous Astro Boy or dancing next to a marionette version of herself. She can make the silliest ideas look like the coolest thing you’ve ever seen. –DG

Funniest song: “Work It”

Nicki Minaj

Nicki Minaj was raised on New York hip-hop in the ’90s, when punchline rappers were the gold standard. Though she’s since become one of the most famous pop artists on the planet, she still seems to get a special kind of kick out of crafting shrewd wordplay and using her distinct Queens accent to bend language to her will. On a verse like her breakout moment from Kanye West’s “Monster,” she flips through alter egos while turning lines about eating brains and being the bride of Chucky into gut-busting words to live by. Sometimes, like on 2010’s “Roman’s Revenge,” all she needs is four words to decimate a rival—“hang it up, flatscreen” is a bar I quote regularly to this day. Nicki’s inexhaustible confidence and playfully vicious energy turns tossed-off jokes into iconic moments that lodge themselves in your brain. –DG

Funniest song: “Monster”

Pimp C

Rappers often say they value realness over everything else, but few embodied that idea the way Pimp C did. As one half of the legendary Texas duo UGK, he was a brash MC who never minced words about what he was thinking and feeling, which made every punchline and put-down worth its weight in gold. It was a joy to hear him tear down rappers who thought they were on top of the world because they rocked Geneva watches with Ferrari kits, and his sex talk was so raunchy it would pull laughs out of you in spite of yourself. “I’m so bad, I could suck my own mothafuckin’ dick,” he once rapped, backed by a thick Texas snarl that gave every word a distinctive ring. Pimp C made plenty of jokes, but those are only half the reason his lines and persona resonate so much 16 years after his death; his brash honesty was all he needed to make even his most benign observations funny. –DG

Funniest song: “I’m So Bad”

Redman

There are jesters, jokers, and rascals, but Redman is more of a wise-ass. He raps like the kid who would be cutting up in the back of math class, shooting spitballs and making dirty jokes during algebra when he wasn’t busy writing the hardest shit you’ve ever heard. On “How to Roll a Blunt,” a standout track from the New Jersey rapper’s 1992 record Whut? Thee Album, he not only delivers on the title but also lays into the people in the cyph with bad technique (“If you’re gonna lick it, don’t drown it with your spit, shit!”) and worse breath (“His breath has the dragon in the dungeon”). And he’s no slouch with the punchlines either, using wild boasts (“I scored a 1.1 on my SAT and still push a whip with a right and left AC”) and self-deprecation to put a smile on listeners’ faces. What other rapper could call themselves “the scrub TLC talked about” on a D’Angelo song and walk away unscathed? –DG

Funniest song: “How to Roll a Blunt”

Rio Da Yung OG

From the ’90s gangsta rap crew Dayton Family to Eminem, Michigan’s rap scene has long been home to MCs with a knack for flipping the darkness of growing up in neglected parts of Michigan into fucked-up comedy. Flint’s Rio Da Yung OG just might have perfected what they started. He always comes through with details that spin what should be stories of desperation into hard-won hilarity. There are vignettes about that time he ran into the dude who stole his bike as a kid and shot him in the leg, or when Rio stole and sold a child’s game system because the kid kept interrupting him trying to bang their mom. His raps are so oddly specific, especially the tales that revolve around local drug business: “I got on sandals, cooking dope at my ho’s house/You know this shit finna be good, I got my toes out.” It’s situational comedy fit for a Friday sequel, delivered in a complete deadpan. –AP

Funniest song: “Legendary”

RXK Nephew

Listening to an RXK Nephew song is like doomscrolling through someone’s unfiltered emotions in a blaring nightclub. Each of the Rochester, New York rapper’s wandering verses read like a series of unhinged non-sequiturs, with intense switch-ups happening from bar to bar. Some lines are funny because they’re clearly jokes and others make you laugh, perhaps nervously, because of the pure shock factor. Analytical breakdowns of the Bible quickly melt into conspiracies about dinosaurs discovering lightning before Benjamin Franklin; ruminations on trauma and nights where he thought monsters were hiding in his closet are interrupted by a claim like, “I ain’t cry about the Twin Towers”; he disses A-list rappers like Kanye West and the producers of his own beats with the same raging level of conviction. Neph’s style is scattered and gruff, which makes it hard to tell whether he’s being silly or serious at any given moment—an expert tightrope act that makes everything he says that much more entertaining. –DG

Funniest song: “American tterroristt”

Shock G

Satirical rap only works if the practitioner deeply understands the rhythms and beats of the genre. Shock G of Digital Underground, aka Humpty Hump, was a master of the form, always knowing the right buttons to push. For example, on “Sex Packets,” instead of imagining a magic pill that will turn him into a human sex machine, like so many rappers would, he dreams up something that would give him the same relief as sex: “No more will I ever have to jack it,” he raps. On “Doowutchyalike,” where he goes back and forth between rapping as Shock and his silly alter ego Humpty, he cracks some jokes that most hyper-masculine rappers would avoid like, “See a guy you like, just grab ’em in the biscuits.” And “The Humpty Dance,” one of the funniest and most feel-good rap songs ever, is a wisecracking subversion of gangsta rap. “All right! Stop whatcha doin’, ’cause I’m about to ruin/The image and the style that ya used to,” he raps, alluding to his prosthetic nose, goofy glasses, and fur hat. Only an aficionado could pull it off. –AP

Funniest song: “The Humpty Dance”

Suga Free

The slick, vulgar, coldblooded vignettes of Suga Free need to be splashed with holy water. It’s pimp-rap, a corner of hip-hop that has generally aged poorly because of its extreme misogyny, but Suga Free is such an offbeat stylist that you can’t help but give in. His motor-mouthed smoothness is part of a storytelling technique that grounds you into the lifestyle and antics of pimping. To complete the picture, he’s got fresh linens and silky, pressed hair that makes him look straight out of a blaxploitation flick. Even if you don’t care for his lyrics, his acrobatic, twisty delivery turns everything he says into (dark, dark) comedy. His songs are horror stories, whimsically told. –AP

Funniest song: “Kitchen Table Freestyle”

Trina

There’s got to be no worse feeling than being on the other end of Trina’s lyrical shakedowns. Her scorn and ridicule is one of a kind, and you can’t help but laugh when she’s in that mode. “Lil dick nigga” is what she calls the man she’s using for her own pleasure on “Look Back at Me,” before ordering him to “get your face down here and eat this pussy” and then scolding him for “fuckin’ all offbeat.” Her delivery is forceful but casual, like she’s barking at you while being fed grapes on her throne. “While his children ain’t home, I make him eat it while my period on/A little nasty ho, red-bone, but a classy ho,” she raps on “Da Baddest Bitch.” It’s a playful reversal of the power dynamics that have dominated hip-hop since its inception, where men talk about women’s bodies like they control them. Don’t try that shit with Trina, she will humiliate you while getting everyone in earshot to point and laugh. –AP

Funniest song: “Look Back at Me”

Trugoy the Dove

As a member of De La Soul, Trugoy had a knack for finding the middle ground between the esoteric and the everyday, cutting through to every kind of listener. His verses are rarely “ha-ha” funny, but there’s a subtle charm to the way he rhymed and observed the world—this is a guy whose rap name is “yogurt” spelled backward, after all. He could find the laughs in the mechanics of romance, navigating the music industry, or calling out posers: “Colombians ain’t never ran with your crew/Why you actin’ all spicy and shiesty?/The only Italians you ever knew was Icees,” he rapped on “Itzsoweezee (Hot),” a goofy line delivered with ease. That wit only sharpened with age and still comes to mind months after his passing in February. Lines like, “Using these minutes like I value the call” from “Much More” can’t help but take on a slightly sadder meaning, even if they still warrant a good laugh. –DG

Funniest song: “Oodles of O’s”