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“You look nervous,” I tell Michael Ian Black, and he readily agrees.

“I went into this conversation, and continue to be in it, with terrible trepidation and angst,” he admits.

Black usually exhibits a preternatural ability to muse on virtually any topic. As a stand-up comedian, his onstage persona can be best described as “smug asshole” (his words). In Wet Hot American Summer, he played a sandpaper-dry camp counselor. On sketch-comedy shows The State and Stella, he cultivated an absurdist meta-comedy that appealed to media-saturated nerds like him. His latest project, a podcast, is a serialized deconstruction of the 19th century Thomas Hardy novel Jude the Obscure, just to get a sense of his esoteric cultural leanings.

But now, he hesitates. He pauses between sentences. He avoids eye contact. He stares at the recesses of the crowded British pub where we’ve met in Redding, Connecticut. He lists his head, a quizzical mien, collecting his thoughts. Every word is measured, every idea thoroughly considered. He barely even touches his fish tacos.

“We suspect there is something inherently wrong with us if we don't conform to some vague idea of manhood. Which is a shame.”

“But I also felt there weren’t many men willing to stick their necks out and talk about this,” Black says after a long pause.

The topic is men—good ones, bad ones, mediocre ones. The well-intentioned, mediocre ones who want to be good, but don't know how. The good ones who aren’t sure how to help them. The defiantly bad ones who won’t even deign the subject at all. And any and all permutations therein.

“And that’s for all the reasons you would think,” he continues. “Guys are in a perpetual competition with each other to figure out where they live in the hierarchy of masculinity. And questioning that is essentially the same as questioning who you are. We suspect there is something inherently wrong with us if we don't conform to some vague idea of manhood. Which is a shame.”

And so Black stands alone as a man willing to acknowledge, challenge, and grapple with the complex, rigid, and deeply ingrained system of unwritten rules governing his own gender. Except he’s not sure what to even say.

“One of the greatest reasons I was reluctant to step into the topic at all was I suspected that to put a toe in it, was to put a foot in it, was to drown in it, and for me that has been born out to be true,” Black says “I’m barely keeping my head above water when talking about this at all.”

Black’s interest in men’s issues began with school shootings. Like many Americans, he was unnerved by the seemingly endless onslaught of mass shootings in our country, but naively believed it’d never happen in his own community. Then Adam Lanza walked into Sandy Hook Elementary School—less than 10 miles from where Black lives in Connecticut with his wife and two kids—on December 14, 2012, and gunned down 26 people, 20 of them elementary school students.

The shooting launched a contentious discussion about why the overwhelming majority of mass shooters are male (and white), and Black shared his own take on the subject in a New York Times op-ed last February, just after the Parkland, Florida, school shooting. “I was just making the obvious point that it’s boys who are doing the killing—and nobody is talking about it,” he says. “And not just in these mass shootings, but in everyday violence. Ninety percent of the time, it’s boys.”

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The column outlined the troublesome state of boys and men in the country, and Black predictably caught all kinds of shit for it from conservatives. Black is now a frequent target of Breitbart’s anti-Hollywood coverage. But it also emboldened him to examine the topic further. “That led to me spending a lot more time thinking about gender, and realizing that issues of gender have been with me since I was a kid.”

Black was raised in what he describes as a “lesbian household” in Hillsborough, New Jersey, with his brother, sister, and stepbrother. His mother and father split when he was five so his mother could be with her female partner, and the result was a bitter divorce. “My mom had a lot of anger towards my dad,” he says, “and I often interpreted that as anger toward men in general.”

Michael with Alyssa Milano in Wet Hot American Summer: Ten Years Later. Saeed Adyani/Netflix/Shutterstock

The term “male chauvinist pig” was common in the house, and his mother and stepmother took the blended family to see Nine to Five, the beloved comedy about a trio of professional women enacting revenge on their sexist boss. “That was the brand of feminism that was in my house,” Black recalls. “It was very present and strident in a way. And as a boy growing up, I remember feeling, Well, wait. My dad’s a boy. And I’m a boy. So…”

What little connection Black had with his father was severed when the man unexpectedly died when Black was 12 years old. Black still doesn’t know the exact circumstances of his death, just that his father was found having suffered some severe head trauma, and later passed away during emergency brain surgery. “I never had an adult man in my life who I was really close to, and I really regret that,” Black remembers. “And my mom, she didn’t understand her boys would need that.”

Instead, Black grew up “suspicious” of men. Most of his friends were girls, probably because he was more inclined to conversation and theater than football and soccer. “I hate this word, because it’s so anti-masculine, but as a kid the thing I was called a lot was ‘sensitive.’ Which I fucking hated. I understood that to mean I was attuned emotionally to what was going on around me. Boys feel like they need to suppress their emotional awareness just to survive, and I definitely felt that.”

One of Black’s most popular bits is about how people often falsely assume he’s gay. “And I’ve had that my whole life. In high school, I had a nickname: faggot.”

It wasn’t just Black’s peers, though. His mother and stepmother also believed Black was gay. They sat Black down when he just 12 and told him it was fine he was gay. “I was infuriated, because it was presumptuous,” he says. “Even at age 12, I knew the way I was expressing myself as a guy was a little outside of the box, and it infuriated me that even in my home it would be misinterpreted.”

“Boys feel like they need to suppress their emotional awareness just to survive, and I definitely felt that.”

He found solace in theater camp—“It was such a relief to me, because it was like, Yes, there are other guys like me, and they’re straight”—but it wasn’t until he enrolled in NYU’s prestigious Tisch School of the Arts and befriended Michael Showalter and David Wain that he felt he finally found his people.

“Neither of us were like ‘Guy’ guys,” David Wain says of his first meeting Black. “We both had a certain revulsion to—What do you call it?—toxic masculinity. And it came out in our work." Showalter describes The State crew as a bunch of “suburban latchkey kids raised on television and renting Blockbuster videos.”

Black quickly proved himself to be one of the strongest writers and performers in the group, according to Wain and Showalter, and Black started cultivating the sardonic humor that would become his m.o. One of Black’s earliest recurring characters was Michael Ian Black, On-Air Personality, a smarmy projection of his real-life self.

“He’s always seen Michael Ian Black as a character he plays,” says Showalter. “But he’s not at all like who is onstage. He’s very introverted, very shy, kind of a loner, likes his solitude. He is not Pollyanna by any stretch. But Mike is extraordinarily decent and kind.”

Black assumed he’d live the starving, New York artist life after graduation, but he never got the chance. He dropped out of school before his junior year to tour the country as a Teenage Mutant Ninja Turtle in promotion for the 1990 movie, and almost immediately after landed his first TV role, starring on the MTV sketch series The State alongside his Tisch improv buddies Wain, Showalter, Ken Marino, Kerri Kenney-Silver, and Joe Lo Truglio, among others. The show ran for four seasons and established the cast as underground comedy stars, a status cemented when more or less the entire cast reunited in 2001 for Wet Hot American Summer. The film was roundly panned (Roger Ebert gave it one star) but generated such a cult following that it was revived for two Netflix limited series.

The cast of The State in 1995. (Black is in back, left of center, in red turtleneck) MTV/Courtesy Everett Collection

It’s provided Black a peculiar kind of fame. He has a small but intensely loyal legion of fans that allow him the luxury of a polymathic career. He’s authored 11 books—two memoirs, eight children’s books, and , a book about America’s political divide he co-wrote with Meghan McCain, daughter of the late Arizona senator—hosted four podcasts, recorded three stand-up specials, and amassed dozens of movie and TV credits. “I have not been doing stand-up comedy for the last year, or year and half because I’ve been so busy with my day job, which is getting television shows canceled,” Black jokes in his most recent special.

To the rest of the populace, Black is probably just the guy who fucked Bradley Cooper in Wet Hot. His Twitter presence (2 million followers) is surprisingly large, however, and affords him an outsize platform for his activism. Yet Black hesitates to call himself a leader. “I don’t feel like I’m qualified,” he says. “I don’t feel like I have the background, I don’t feel like I have the voice, the visibility. But what I feel like what I can do is, in some way, use my small voice to help guys who don’t understand these questions and issues, don’t know how to speak to women and don’t understand their perspective, I hope that I can be a little bit of a go-between.”

Black drives us home from the bar in his silver BMW, looking every bit the suburban, 47-year-old dad he is—plaid, button-down shirt; khakis; mid-life crisis vehicle; jet-black hair combed neatly to the side; and eyes laser-focused on the road as he guides us through the treacherous Connecticut hillside (he doesn't care for Los Angeles) in a late summer rainstorm.

“When you talk about redefining masculinity, you talk about, in some way, rejiggering the entire world,” Black tells me, intently staring ahead. “And that’s not a topic anyone wants to talk about, because it’s like, Well, what the hell do we do? It’s much easier to just surrender to the current structure and say, ‘I’m going to do the best I can within it.’ And I guess, ultimately, that’s what I’m saying, too. I’m not out here trying to save the world and overturn capitalism and stop all war. I’m really just out here trying to get guys to feel better about themselves.”

The discourse around toxic masculinity—a term Black tries to avoid, as it often seems like an all-out indictment and a non-starter for most dudes—is fraught, especially when it plays out on the Internet. It’s no wonder, then, some men would rather not participate in the debate at all. But that presents its own quandary, in that it’s impossible to resolve men’s issues if men choose to ignore them (which, ironically, is the source of these problems to begin with).

David Wain, Michael Ian Black and Michael Showalter on the set of Stella in 2005 Comedy Central/Courtesy Everett Collection

Getting men to feel marginally more comfortable with themselves—with their thoughts, their failures—seems a valiant immediate goal.

But even that’s tough to accomplish in a social climate that rewards knee-jerk reactions and eschews nuance. To participate in the gender dialogue as a man, even as some well-meaning mediator, means to inevitably fuck up, to say the wrong thing and incur the wrath of online commenters. For Black, that eventuality came when he decided to defend Louis C.K.’s recent stand-up comedy comeback.

In late August, disgraced superstar comic Louis C.K. performed his first stand-up set since he was outed a year earlier for masturbating in front of female peers and colleagues throughout his career. The performance was controversial enough itself, but Black stoked the debate when he defended C.K. and other men’s right to “move on with their lives.”

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Wow you’re so brave to be willing to take the heat! Here’s some: literally no one was waiting for you to weigh in on this, homes. Stop being a messy bitch and get your life together. — Alice "Defund the Police" Wetterlund (@alicewetterlund) August 28, 2018

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Wow, very disappointing to hear from you. How did he "serve time"? By laying low for 9 months? God forbid we hold powerful men accountable for the women they've abused and silenced. No, no, let this man get back on stage for 15 minutes to tell jokes! — Anna Akana (@AnnaAkana) August 29, 2018

Black later clarified his tweet was born out of a sense of mercy, and intended to start a discussion about when, if ever, these men can be forgiven for their sins. But the backlash against Black was swift and fierce; he had already been pilloried by hordes of disappointed feminists.

“I immediately regretted it,” Black tells me as we approach his woodland manse. “What I didn’t recognize is that so many women still don’t feel seen or heard with this issue. And I was already pivoting to, ‘How do we help the men here?’ That was totally the wrong question to ask, because the women need to come first.”

Black pulls into the driveway. The house is unassuming from the street, obscured by a thicket of wilderness that opens up at the driveway to reveal the stately, contemporary forest home Black and his wife had built from the ground up.

He parks the car in the garage, but doesn’t turn it off. Doesn’t even take off his seatbelt. Rain pours on the cement driveway behind us as Black sits and ponders.

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Thing is, Black does believe the redemption conversation should happen at some point. “To me, having empathy for somebody like Louis does not negate the empathy I have for somebody who’s a victim of somebody like Louis,” he says. “Those things are not mutually exclusive.” And his experience voicing that sentiment speaks to a larger concern not in just the gender wars, but in our general public discourse: How do you get people to engage each other in good faith when the threat of condemnation is so high?

“I have a lot of sympathy for the defensive crouch a lot of men feel like they’re in right now. A lot of guys want to be as supportive as they can, but really worry about saying the wrong thing,” Black says. “But if you’re not fucking up sometimes, you’re not asking hard enough questions.”

For a template, he points to his friendship with McCain. “One of the things I’ve always admired about her is she was always more receptive to hearing other points of view than I was… The left that is falling into the same trap the right has, which is the ideological purity tests. We’re all too happy to cannibalize ourselves. And I don’t want to play that game.” (McCain did not respond to an interview request.)

Black and Meghan McCain promoting their book America, You Sexy Bitch on June 20, 2012 in NYC. Cindy Ord/Getty Images

Inside, Black fixes himself a cup of English breakfast tea in his modern, minimalist kitchen and retreats to a brown sofa in the family room—a vaulted ceiling, a 360-degree fireplace and, like every room in the house, it’s exquisitely decorated by Black’s wife, an interior decorator.

At home, Black’s anxieties are shockingly relatable. He worries about money: “This fucking house is expensive.” His career: “The TV shows aren’t coming in the way I want.” And he wonders if pursuing his various interests is what’s prevented him from achieving sustained, mainstream fame.

“Mike is so talented, and has so many different interests, and is skilled in so many areas that he hasn’t been the guy who is just one thing,” Wain will later tell me. “He hasn’t had that one thing that catapults him into that next level. But who knows what the alchemy is that makes that happen."

Recently, Black mostly wrestles with how to make all this gender stuff funny. Contemporary comedy audiences expect material not only to be funny, but also socially conscious. (The runaway success of Nanette, Hannah Gadsby’s 2018 Netflix special about her struggles as a queer woman, being the foremost example.) Laughs are no longer a goal unto themselves; they must be achieved authentically and without offending marginalized groups.

“I love silliness and absurdity, and I love surreal shit. I don’t always want to be earnest and sanctimonious.”

“I’m always conflicted about this, because I love silliness and absurdity, and I love surreal shit,” Black says, speaking softly yet quickly. His labrador retriever Ole (pronounced Ollie) sits at Black’s feet, Black petting and scratching him as he considers the patriarchy. “I don’t always want to be earnest and sanctimonious.”

Learning how to approach social topics in ways both incisive and funny has always been the comedian’s task, and Black thinks the jokes will come in time. He’d like to create a stage piece centered around gender issues, and he is already working on a book about the subject.

The bigger challenge for him is the authenticity bit. Growing up, Black was enamored with John Belushi and the mythos that surrounded him, how it was never quite clear where Belushi the man ended and Belushi the character began. Black sought to create a similar tension between his on- and offstage personas. “This totally self-confident, kind of smarmy, self-absorbed, narcissistic dude was a projection of who I wanted to be in a way. But for the past several years, this idea of trying to be a more authentic version of myself onstage has consumed me.”

Black has been doing more confessional stand-up in recent years, cracking jokes about the trials of marriage and fatherhood. By comedy standards, it’s a backwards career. He started a successful TV actor and has ended up a stand-up, struggling to find his voice.

“I worry the more authentic version of myself isn’t that funny,” he admits.

Michael Ian Black is nervous (again).



Two days after our interview, he’s scheduled to appear in Brooklyn at a women’s empowerment conference hosted by the New York Times. He eats a conference-provided, family-style lunch with several other women attending the festival as spectators, none of whom recognize him.

“At first I was reluctant to do this because I didn’t want to pretend to be an expert on something I’m not an expert on. But I eventually realized that if I’m going to do this, I better embrace it and do it,” Black concedes. “But it terrifies me.” A startling admission from someone who’s spent his entire adult life performing.

Black performing at the Shoreline Amphitheater on June 24, 2017 in Mountain View, California. Miikka Skaffari/Getty IMages

Black’s session is with former NFL player Wade Davis, the only gay player in the history of the league, and is titled “How to be a Male Ally”—a term Black struggles with.

“I’m conflicted by that word, ‘ally,’” Black says. “Being an ally, to me, means being a perfect ally. It implies a passivity and an unquestioning allegiance. It doesn’t allow you to have independent thinking. And I don’t believe in unquestioning support.”

Black gives a more palatable version of that spiel onstage. “I don’t think there’s a good answer [for how to be a male ally] yet. Alliance to me is more about supporting values than it is to support a specific person. I don’t know as a male ally, for instance, I support Sarah Palin. She has values that I reject.”

For all his activism, Black is pessimistic about the immediate future for men. It took feminists more than 150 years—starting with the first Women’s Right Convention in 1848 in Seneca Falls, New York—to go from advocating for the essential rights of human beings to being able to oust serial predators from the workplace, he says. If a similar change is to occur with men, it, too, could take generations.

“This topic is such a vast and profound one, and the conversation, in any meaningful way, hasn’t even really begun, especially if you compare it to feminism,” Black says. “That being said, it does have to start. And I feel like if I can do anything, I can nudge the conversation just slightly to the mainstream.”

Black leaves shortly after his panel ends. By this time, it’s late afternoon, and the vast majority of conference attendees have left the conference room to gather in the lobby. And as Black walks outside to his car, he passes a large and swelling group of women huddled around a TV, literally eating popcorn as they watch Brett Kavanaugh, red-faced and yelling, angrily deny the accusations made against him by Christine Blasey-Ford.

Occasionally, the women gasp in unison, such as when Kavanaugh screams at the Committee members. But more often than that, they laugh at him.