Nick Kroll discusses lessons he’s learned in comedy, including how an applicator tampon works.

Nick Kroll is always changing and somehow everywhere. On Kroll Show, his three-season sketch comedy show, Kroll rotated through dozens of characters from Larry Bird the basketball player to Liz the insufferable PR to Bobby Bottleservice the ultimate douchebag. On Big Mouth, his Netflix animated series, Kroll voices at least six characters, human and otherwise. He also spent 15 weeks alongside John Mulaney on Broadway with Oh, Hello, playing Gil Faizon, a septuagenarian with all the worst habits and thoughts you can imagine. And has dabbled in a bit of drama, acting in Loving and Adult Beginners. He’s everywhere, but very rarely is he Nick Kroll.

With his Middle-Aged Boy tour, which includes one night only in Auckland on January 9, Kroll is himself. After two decades of portraying and exposing every type of person under the sun, Kroll is turning his gaze inwards in his stand-up show. “I ended up deciding that I, Nick Kroll at 41, am the target of my jokes,” he says, walking and talking Sorkin-style on the streets of New York. “It’s an examination of who I am, where I am in my life more so than looking outward at culture or other people. It’s really a look at who I am and trying to come to terms with that.”

The tour, Kroll’s first international stand-up tour, follows a sold-out tour of the United States, though he admits to only performing in Commonwealth countries (Canada, England, Australia, New Zealand) “to just stay within Her Majesty’s domain.”

Having never visited, let alone performed in, New Zealand or Australia, Kroll isn’t too worried about his humour not translating. The name Nick Kroll doesn’t hold the instant stand-up recognition of the likes of Hart, Rock, and Seinfeld, but his humour has largely been popular since the world moved online, making it immediately universal. At least, he hopes so. “While we all have these specific experiences and senses of humour, the way the world works and how interconnected it is, we now have a much more shared sense of humour and points of reference in a way that we didn’t five or ten years ago.”

At the same time, the internet allows for past work to be exhumed, no matter how much a comedian has evolved (or not). Just ask the annual Saturday Night Live hire whose social media history reveals all sorts of questionable takes. Having played so many characters on so many platforms, including the ten-year-old Comedy Bang! Bang! podcast, Kroll has certainly pushed the boundaries of decency with some of his characters, never shying away from portraying different genders and ethnicities. I ask about how his characters have aged and if there are some he wouldn’t feel comfortable portraying anymore. He answers quickly, “yes.”

“There are definitely characters, and maybe the context within characters of how they exist, that I am a little less likely to do because I think the media landscape has changed. Sometimes there are characters that I wouldn’t do how I did them but maybe they still would exist in another framework. Certain things I would’ve done ten years ago I wouldn’t do now both because they might not seem entirely appropriate now and also because they’re just not interesting to me anymore.”

For Kroll, the joke is not that he is acting as a woman, it’s that the woman is going through something funny. “I try to follow my own moral compass and try to navigate who is the target and what is funny about it? In the case of Liz [from Kroll Show’s Publizity sketches] getting bangs, it’s a universal question of taking the leap to get bangs. Now, more than in the past, you have to take a look at what is the target of your joke and what are you choosing to talk about.”

In Auckland on the 9th, Kroll has chosen to talk about himself and his experiences of straddling the two worlds of childhood and adulthood, hence Middle-Aged Boy. Kroll is unmarried and has no children, and spends a large portion of his time doing funny voices on an animated show. And when I ask him if he learned anything new in the process of writing Big Mouth, a show about puberty in all its iterations, he responded with something every boy should probably learn before they’re 41.

“Last year in the room we were talking about periods and one of our writers brought out her tampon and I saw how a tampon applicator works for the first time. I’d seen tampons, obviously, but I’d never seen what an applicator looked like. The mechanics of it was very exciting and interesting in a way that I had never quite seen or experienced before. That’s what our room is like every day. Our room is sharing our experiences that boys have heightened emotions and that girls are horny and everything in between. My goal in making the show is that kids can watch it and adults who have gone through it and are looking back on it can watch it and feel like they’re not alone. That they weren’t alone going through it. That we all experience this thing.”

Big Mouth, a show about Kroll’s own experiences of puberty (alongside his best friend and co-creator Andrew Goldberg) is arguably his best work to date. Finding comedy in his own life and feelings has proven to be a universal hit, with thousands of viewers seeing themselves in his stories. Middle-Aged Boy follows that impulse, not acting as an official continuation of Big Mouth but a “further examination of what the human experience is in my particular case and the lessons I learned.”

Buy tickets to Middle-Aged Boy here.