Aziz Ansari

Aziz Ansari photographed by Wesley Mann at The Wilbur on April 30, 2014 in Boston. 

Wesley Mann

Aziz Ansari’s comedy career is growing faster than the sinkhole that swallowed him in This Is the End, thanks to a biting and brainy comedy style that is breaking box-office records. Now, with plans to headline New York’s biggest arena, and a $3.5 million deal to write a book on modern romance with an NYU sociology professor, the Parks and Recreation star grouses about his generation: the "rudest," "flakiest," "worst" one ever.

On the evening of May 5, Aziz Ansari sits in a tiny dressing room backstage at Boston’s Wilbur Theatre, about to perform his new stand-up show, Modern Romance, before a sold-out house of 1,200. “This is the 10th show here at the same venue, and it’s cool but it gets a little repetitive,” says the 31-year-old Ansari, who’s wearing a burgundy velvet jacket and black everything else. “It’s kind of nice to travel and do different venues. Each theater has a different vibe, like you wouldn’t think, ‘Oh, Springfield, Mass.!’ But it was a beautiful, really nice 3,000-seat theater. I like new crowds so this has been a little bit weird, because it’s the same thing so many times.”

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Ansari doesn’t mention that by selling out 10 consecutive shows he has broken a record at the 100-year-old Wilbur. His demeanor is so calm it’s disconcerting. Zero trace of the intense, hyper-active, fast-talking character he will become in a half hour. “Yeah, well, that’s the thing: Any high-energy comedian like [Dave] Chappelle or Chris Rock, they’re generally, like, pretty low-key dudes,” he says. “Like, that’s the stage, that’s how you’re performing. But if I was like that in my regular conversation, it would be very annoying.”

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This string of packed houses is the latest validation of Ansari’s meteoric rise to the top of the comedy world. He is an exemplar of the explosion in the business of live comedy, where a growing number of performers — like Ansari, Louis CK and Chelsea Handler — mix theater and arena dates. Sources estimate a comedian of his stature could make $10 million or more a year from live dates. He has done it with biting and brainy analytical humor that comes from serious study of the wired, ADD-plagued world around him. 

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In addition to all his accomplishments — a starring role alongside Amy Poehler on Parks and Recreation, which just has been renewed for its seventh season on NBC; four comedy specials; and countless tours — he also is writing a book for Penguin Press, due in 2015, on modern love, with Eric Klinenberg, a sociology professor at New York University (NYU) and author of Going Solo: The Extraordinary Rise and Surprising Appeal of Living Alone. His reported advance: $3.5 million.

The crowning achievement, though, may be a solo date at New York’s Madison Square Garden that’s being hammered out for the near future. It marks a level of popularity that few comedians have ever attained. Even Ansari, who prefers the intimacy of smaller venues, expresses amazement at the possibility. “There is something very insane and amazing about starting stand-up in New York City at the lowest rung — open-mic spots — and then many years later going to the other utmost, utmost extreme of playing Madison Square Garden,” he says. “I felt a sense of that when I did Carnegie Hall, but Madison Square Garden is another level.”

Before leaving Bennettsville, S.C., to attend NYU in 2001, Ansari thought about double majoring in biology and business. He decided on marketing instead but during his freshman year, he did an open mic at the Comedy Cellar in Greenwich Village, and he had found his calling.

“It has been pretty fast for me, in a sense, because I did one tour where I did, like, 300 rock clubs, then I put out a special, and after that I started doing theaters,” he says. “Now it’s just like bigger theaters and more nights in the theaters. It was a pretty swift change.”

The day after Billboard meets Ansari, he and Klinenberg fly to Paris to talk to French people for their book. “I love talking to people,” he says. “Aziz is a real interviewer, by which I mean he listens to people and takes them seriously,” 

Klinenberg says of his co-author. “He’s probably a better sociologist than I am a comedian.”

Ansari realizes the inherent challenges that come with trying to sell a book today. “I think the problem now is our tolerance for boredom is getting ridiculously low,” he says. “Like, you’re having a conversation at dinner and your instinct is to pick up your phone. We’re just more likely to do that because we’re used to the stimulus.

You know Spotify? Something like 48 percent switch to the next song after five seconds. You don’t have five seconds to give this f—ing song a chance? You’re not going to listen to 'Bohemian Rhapsody’ [for] five seconds?”

The research trip to Paris will take a week, and when he returns, Ansari has nine shows scheduled in the Midwest, then a couple in Montreal. 

The schedule sounds grueling, but he’s not complaining. “As a comedian you don’t have to do a lot,” he says. “You kind of get to hang out most of the day until the show, so I usually explore the town a little bit.”

Like many comedians, Ansari considers live performance to be an essential part of the trade. “There’s a really fulfilling feeling of writing a new hour of material, touring it and having people leave the show at the end and think, ‘Shit, that was even better than last time,’ ” he says. “There are bits that I do in the show that have taken me a long time to really tinker with to get to a certain point where they have a certain finish at the end.”

As soon as Ansari walks onstage at the Wilbur, the response is ferocious, almost terrifying. Early on, there is one instance of inappropriate yelling. 

Ansari tells the girl to clam up and casts a spell for the next hour-plus as he diagnoses modern love and various ills in the modern world: how addicted we are to our gadgets; how, rather than help us communicate better, they often assist us in deceiving others and hurting relationships.

Even his own nine-month relationship is fodder and, he says, shaped the show’s content. “I met her years ago when she was seeing someone,” he says of his girlfriend, whom he declines to name. “I thought she was really cool. Then I ran into her randomly and she was single.” Since that fateful encounter, he says, “I’ve kind of settled down. 

I was the guy eating Skittles and having lots of fun, and then I was like, ‘I need a nice nutritious salad’ — she’s the salad.” It’s an apt description.

Ansari is a famous foodie and a source says his girlfriend works in the food industry. His show at the Wilbur is a perfect marriage of hilarity and wisdom. The eruptions are constant, but periodically everyone simmers down and listens, respectfully. If there’s a larger purpose to Modern Romance, it’s to cast light on the sometimes absurd way that social norms have evolved. Onstage, Ansari refers to his generation as the “rudest, flakiest” and “worst” one ever, and doesn’t let himself off the hook. He’s confessing, making personal experiences funny, even mundane matters like buying a toothbrush: 

"Before leaving my house without even thinking about it, I Google 'best toothbrush.' Forget the mediocre toothbrushes of the past ... I'm reading article after article about, like, the pros and cons of bristle strength.” Finally, he buys a toothbrush. “And you know what? It’s a pretty good toothbrush," he says. "You know what’s a good toothbrush, though? Every toothbrush!" explodes Ansari, provoking gales of laughter. 

"No toothbrush is bad!" 

For an encore Ansari tries out some new bits, takes requests (there are cries for old favorites like “Grapefruit!”), and then makes his exit.

Backstage, he talks about why he likes putting thought-provoking ideas out there. “When you do these talk shows or when you’re performing here for thousands of people — like, people will listen,” he says. “You can kind of talk about anything if you just make it funny."

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