Nick Kroll’s Premature Exasperation

Timing, they say, is everything. Nick Kroll learned this the hard way at 13. “I was very small in seventh grade, and a very late bloomer,” he recalls. “I just felt like, ‘Why haven’t I hit puberty yet?’” His tween angst reached its nadir during one especially untimely incident: “Some girl pulled my pants down and my underwear came off as well, right in front of my crush. That was, uh, slightly upsetting.”

Whatever his shortcomings back then, Kroll, 40, has since fully developed into one of Hollywood’s most creatively endowed comedians. His timing’s pretty on point, too — this fall, after starring as a smacktalking baller in summer comedy Uncle Drew, he’ll revisit his awkward adolescence in the second season of Big Mouth, the Netflix animated series he co-created with his real-life BFF Andrew Goldberg. But before that, he takes a serious turn hunting Nazis (alongside this month’s Sharp cover star Oscar Isaac) in historical drama Operation Finale — which, sure, for a dude best known for playing schmucks (from a shock jock on Parks and Recreation to a literal douchebag in Sausage Party) may seem a bit of a stretch.

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However, Kroll’s got more period piece experience than you’d think. He remembers a sketch comedy tape he made in high school with Goldberg. “One of the first characters I did, weirdly, was a parody of [McCarthy lawyer and eventual Trump mentor] Roy Cohn,” he says. “I’ve strangely always enjoyed historical stuff.” Kroll’s knack for fleshing out ridiculous characters — particularly the blustery, self-absorbed ones we’d later see him play on Comedy Central’s Kroll Show — would become his own personal life hack. “For a little guy, comedy was a way to get bigger, have an attitude, and find a way to make girls like you. It’s also a weapon — if you’re funny, you can use it to scare off bullies.”

And while cracking wise has taken Kroll pretty far, he’s not quite ready to ditch his hormonal baggage yet. Rather, he now mines it for Big Mouth, in which he plays a preteen version of himself grappling with puberty. He calls it the most vulnerable thing he’s ever done, and for good reason: this season, he recreates his aforementioned wardrobe malfunction. “If I don’t win an Oscar for my work in Big Mouth,” he muses, “then I don’t know what is happening in this industry.”

Kroll kids, but it wouldn’t be preposterous to imagine him one day snagging Hollywood hardware in a sad-clown phase of his career. Not that he’s in any rush — his next role is the voice of Uncle Fester in the animated Addams Family reboot. “I like having the variety of being on and off camera,” he says. “I get sick of my face and I assume other people do, too.” And yet, something tells us we’ll be seeing much more of it — when the time is right.

Funny Guy

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A denim jacket under you suit? Some might call it cheeky. We just call it awesome.

DENIM JACKET ($110) BY LEVI’S, SUIT ($3,195) BY ERMENEGILDO ZEGNA, SHIRT ($565) BY ERMENEGILDO ZEGNA, SUNGLASSES ($700) BY TOD’S.

FIT TO PRINT

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With careful attention to fit, this T-shirt and suit combo is simple and perfectly executed.

SUIT ($1 ,695) BY BOSS, SHIRT ($125) BY BOSS, SHOES ($110) BY ADIDAS.

Peaked Interest

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Widen those lapels if you want to look like you own the place. The all-black monochrome doesn’t hurt, either.

SUIT (PRICE UPON REQUEST) BY DIOR, SHIRT ($740) BY DIOR, SWEATER ($880) BY DIOR.

SHAKEN, NOT STIRRED

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Mix up a classic look with an extra-bright colour or a subtle detail, like pleated pants.

SWEATER ($935), SHIRT ($1 ,090), TIE (PRICE UPON REQUEST), AND PANTS ($995) BY LOUIS VUITTON.
PHOTOGRAPHY: STORM SANTOS
STYLING: JEANNE YANG/THE WALL GROUP
SHOT AT: SOFITEL LOS ANGELES AT BEVERLY HILLS
Grooming: Daniele Piersons/Art Department