50. Wanda Sykes
The title of Wanda Sykes best special to date – 2009’s I’ma Be Me – gives a sense of exactly what people can expect from her. A veteran of The Chris Rock Show‘s writing room (the comedian had given her an early break by asking Sykes to open for him on tour), she’s managed to project both street smarts and confessional intimacy while onstage, which give an audience the sense that they’re getting the real deal. While talking about getting waxed, she might liken her tender parts to a hunted animal crossing the Serengeti (“Come on, asshole, run!”) or confess how much harder it is to be gay than African-American: “I didn’t have to come out as black. I didn’t have to sit my parents down and tell them about my blackness.”
49. Aziz Ansari
Forget the “Raaaandy!” character – even without his fictional fratboy persona from Funny People, there’s few working stand-ups today that are as infectiously enthusiastic onstage as Aziz Ansari. The Indian-American comedian’s early routines focused on the simple pleasures of pop culture, hanging with celebrities and enraging his cousin Harris online, all infused with a sense of endearing manicness. Once he’d moved on to playing arenas and tackling more mature themes – relationships, the dehumanizing effects of technology, the experience of his parents moving to America – Ansari has also begin to find depth as well as volume in his comic sensibility. And as his killer recent SNL monologue about the casual racism of the new “lower-case kkk” alt-right proves, he knows exactly how to integrate socially aware comedy into his hyped-up “can you believe this?” sensibility.
48. Margaret Cho
Think back to Margaret Cho’s first HBO Comedy Half-Hour, and the young comedian whose material ranged from how she might get laid after two years of celibacy (answer: cover her vagina with leaves and hope somebody falls in) to life growing up with a loud, Korean mother running a bookstore that sold gay porn (“What is ass master?!”). Since then, Cho has grown even more comfortable in her skin, and even more candid about her preoccupations. Recent tours (with names like “PsyCHO,” “Cho Dependent” and “Mother!”) prove the San Francisco native hasn’t become shy or squeamish with age. Her willingness to talk periods, colonics and her life as a “dick widow” – a woman whose friends are primarily gay men – make her the sort of funny, sex-positive feminist and LGBT activist younger comics continue to look up to.
47. Elayne Boosler
Imagine the prototypical female comic of the 1980s: Big hair, suit jacket with shoulder pads and the sleeves rolled up, the ubiquitous brick wall behind her. You’re imagining Elayne Boosler – but before that image became a cliché, it was just part of the stand-up act she had been honing for years. At a time in which women comedians were not talking about sex, Boosler addressed it head-on (“Men want you to scream ‘You’re the best!’ while swearing you’ve never done this with anyone before,” was an early, signature line). She was also key in convincing the industry to pay attention to women: In 1985, without a network to support a comedy special, Boosler financed the production of one on her own, titled “Party of One” – and when that became a hit, Showtime signed her for several more. She was the best at what she did, so much so that everyone kept copying her until the Eighties comedy boom went bust. Accept no substitutes.
46. Reggie Watts
He’s cited Monty Python and Bugs Bunny as seminal influences – which should surprise no one who’s seen Reggie Watts’ combination of lighthearted, unpredictable lunacy. He riffs about space, time and why no one needs to eat a whole croissant; he creates hip-hop jams about boning and soul ballads about big-ass purses; he gets caught in fast-forward motion, holds forth in jibberish French and foppishly fumbles with his mic stand for minutes at a time. An impressive vocalist and musician, Watts has a knack for pushing past staid jokes to playing with the rhythm and sound of words; it makes his act both thrilling and impossible to categorize. And his special A Live at Central Park will help viewers imagine a freaky future in which stand-up, improv and music can all coexist under one anything-goes Absurdist sensibility and one angelic halo of an Afro.
45. Freddie Prinze
A few years after dropping out of high school to work New York clubs, a cherubic 19-year-old Puerto Rican named Freddie Prinze exhibited his preternatural command of stand-up on The Tonight Show, and the rest was history. Though the charming, mustachioed kid had nothing but potential, he got caught up in the Seventies drug culture and had problems dealing with a dizzying rise to fame after Chico and the Mantook off; he would commit suicide at age 22. But though he had only one album (“Looking Good”) and one early HBO special, his legacy looms large. Take his ingratiating presence, casual tone, autobiographical subject matter and the gentle ribbing he gives himself—down to the introductory portmanteau he used to explain his biracial heritage, “Hungarican” – and you’ve got the template for half of the acts coming up in the backrooms of New York bars today.
44. Russell Peters
Arguably the first truly global stand-up superstar, the Canadian-born Russell Peters jabs not only those of Indian descent – he ribs nearly every ethnicity you might rattle off on an intimate, country-by-country basis. His incredible eye for detail and gift for mimicry allow him to shout out to his dynamic, racially-mixed audiences (“Any Filipinos in the house?”); his broad characterizations play fast and loose with stereotypes, though how many other comics have a solid 10 minutes on the differences between Mandarin and Cantonese? He’s virtually unrecognized in American showbiz, but YouTube clips of his act have connected him to an enormous audience around the world, he’s been on the Forbes list of top-grossing comedians for years. More than a few of young comics from outside the U.S. have Peters to thank for their introduction to the art.
43. Amy Schumer
She has trumped the sex talk of swaggering and sad dudes, making it the domain of anyone passionate or foolish enough to face it in all its awkward, sloppy and painful dimensions. But what distinguishes Amy Schumer – what makes her one of the most exciting comics working today – is that her wit is as fearless as it is fierce. She doesn’t mind shocking a crowd to make her points, and couches tough notions in cute packages. (On taking Plan B and going to yoga: “Can these people tell I’m mid-aborsh?”) And while her range (and her politics) come out more in her sketch show Inside Amy Schumer, her stand-up stings the most when she looks at how women are punished for seeking pleasure – in men, in food, in hedonism, in feminism, in liberation, in life.
42. Phyllis Diller
With her garish, glittery outfits (“I used to work as a lampshade in Las Vegas”) and hair standing on end, Phyllis Diller’s freaky fabulousness made her audiences sit up in their chairs. From there, she cracked clever jokes about her looks, her children, her husband “Fang,” her mother-in-law, her domestic duties and eventually, her age. “You know you’re old,” she’d quip, “when they discontinue your blood type.” Many have tried to imitate her gruff guffaw; no one could duplicate her unmistakable look and or her way around a sharp, Vegas-ready one-liner. The first female household name on the list, she convinced legions of early stand-up audiences that women comics were not a novelty but a forced to be reckoned with.
41. Bernie Mac
“I ain’t scared of you motherfuckers” – it was the large-and-in-charge line that launched a career and turned Bernie Mac’s appearance on the original Def Comedy Jam into a flashpoint. His legendary set solidified the Chicago native as a big, braggadocious comic with a peculiarly magnetic delivery and a habit of squeezing every last bit of air from his lungs to make a point … especially if that point was embedded in one of his exasperated stories of child rearing. “See, I’m from the old school. I’ll kick a kid ass,” Mac would explain in Spike Lee’s The Original Kings of Comedy concert movie, before imagining the boxing match he’d have with his sister’s two-year-old. Politically correct he was not. But the late, great Mac’s wide-eyed, foul-mouthed charms spoke directly to black audiences – and anybody savvy enough to catch on – in a way that put him head and broad shoulders above his peers.