Ansari’s first special, Intimate Moments for a Sensual Evening, came only five years ago, and by that point, his act was already filled with anecdotes about hanging out with famous rappers. Both that and his second event, Dangerously Delicious, were fairly disjointed hours with no real organizing principle to them, mostly skating by on Ansari’s infectious enthusiasm for every story he told. 2013's Buried Alive was a big leap forward—a more introspective look at his life as a single guy surrounded by friends who were pairing off and having babies. But even as he complained about the pressure of getting older, it still felt like Ansari wasn’t really letting his guard down.
On Live at Madison Square Garden Ansari maintains his goofy, kid-like energy (and at one point does an extended impression of Ja Rule), but he also tells much longer stories, and seems much more comfortable slowing down the pace. His first chunk of material is about his awe at the decision his parents made to emigrate from India to South Carolina, and their early struggles in the States—it’s heartfelt without ever getting too saccharine, but even better, he lets it breathe onstage without delivering a ton of rapid-fire punchlines. It’s always impressive when a stand-up can command a crowd with quieter material, but it’s particularly impressive when it’s happening in a colossal, sold-out venue.
Live at Madison Square Garden isn’t as organized around a central theme as Buried Alive was, but each chunk is long and carefully considered, and at no point is Ansari yakking about his life hanging out with famous people, which used to be the backbone (and the most tiresome aspect) of his stand-up. A section on the harassment women face on a daily basis both online and in-person doesn’t feel didactic or egotistical, but rather a worthy use of the huge platform Ansari has; a later segment on the flakiness of the smartphone-owning generation rings true with personal detail, rather than sounding like an Andy Rooney rant.
A huge arena like Madison Square Garden is almost impossible to work to a comic’s advantage—the energy has to be dialed so high to get the crowd going that it makes sense Rock, Cook, and Hart have all succeeded in the space. Ansari doesn’t even try to emulate them, though some of his weaker moments come as he conducts “clap if you agree” insta-polls with his audience, which is tough to justify unless it supports some grand point or punchline. A moment where he reads a random audience member’s text messages is astonishing simply because it works at all—no great endorsement, but getting anything from a bit that risky, with a crowd that large, is impressive.
But what’s next for Ansari? The legacy of stand-ups who've made it to this level is pretty daunting, and there’s no higher rung on the ladder to reach. But he’s also clearly committed to improving his craft, and openly talks about his growth since his first special. That progress is apparent: Ansari might not ever be able to transcend the hype he’s contended with from the beginning of his career, but at least he’s not content to coast on it.