On a Monday night in October, Judah Friedlander and I witnessed history. We were meeting at New York’s Comedy Cellar to talk about his new book, If the Raindrops United, when Tracy Morgan showed up unannounced to do his first stand-up set since his near-fatal accident 16 months ago. After Morgan’s brief but powerful show, he and Friedlander hugged, rejoicing in the former SNL star's return to live performance. “You picked a good night to come,” Friedlander told me.
But really, any night Friedlander is at the Cellar is a good night to come. He’s been performing there for more than 20 years. He knows the wait staff at the upstairs restaurant, Olive Tree Cafe, by name. He doesn’t need to look at the menu to order. The Cellar is his playground.
Friedlander, 46, is recognizable from years of stand-up, his supporting parts in more than 20 movies, and perhaps most notably, his role as a schlubby staff writer who constantly exasperates Tina Fey on 30 Rock. His signature trucker hat and T-shirt reading “World Champion” are his trademark uniform. For those who are less familiar with his work or don't follow his Twitter account, it might come as a surprise to learn that underneath his slacker duds is a comedian with a strong activist bent. His sets regularly touch on hard-hitting topics like gun control and racism in America.
“Sometimes I think when you’re doing something that’s funny but it’s about serious topics, people don’t realize that what you’re doing is also serious,” he told me over dinner. It's true that even the most profound discussion of, say, the wage gap in America can get diluted in the laughs Friedlander elicits. But he's committed to speaking up: “Most progress doesn’t happen if you don’t fucking talk about it."
Or, in this case, draw about it.
If the Raindrops United, which goes on sale October 20, is a book of satirical drawings that comment on the everyday inequality and absurdity we witness in our country, tackling everything from gentrification to the dynamics of power between the sexes. Though it's a collection of illustrations, it captures the clever way that Friedlander has successfully addressed these topics in his stand-up — visual jokes that make you think. (It's a touch more serious than his first book, a satirical guide to martial arts.) The title of the new volume comes from Friedlander's rather utopian idea that just because something is small doesn't mean it can't also have an impact. “If people came together, they could have a lot of fucking power, more than they realize,” he said. “A lot of people feel powerless, and as an individual, a lot of people are powerless. But, if people unite, accept each other, come together, and work for a common cause, nothing can stop them,” he said. This idea is cleverly illustrated on the cover, which features a Godzilla-sized raindrop falling on Manhattan. It’s right below these words from his former boss, Tina Fey: "Judah has drawn a weird and funny book in the grand '70s tradition of B. Kliban! I think this book will probably fix the world." Raindrops offers a clear sense of what's important to Friedlander. After spending time with him, I realized it's the smaller details that reveal the most. Take, for example, the small bottle of hand sanitizer he keeps in the side pocket of his jeans. “Oh yeah,” he said, chuckling, when I asked him about it. “I forgot that was in there. I can be kind of a germaphobe.” He also keeps small notes in his front pants pockets, folded up haphazardly. When he pulled them out to show me how "unorganized" he is, it was like looking at the innards of a distracted middle schooler’s backpack. They were mainly set lists, notes jotted down but not yet fleshed out. “See, this one fell apart,” he said, pointing to one segment of paper with a few words scrawled on it. “I’m already worried that I lost the other half of this.” (Turns out he didn’t.) “I definitely have OCD paranoia problems. That can inhibit you from doing stuff sometimes. I have trust issues with people as well. “It’s extremely stressful," he continued. "Imagine if you thought every time you tie your shoe, you fear that not only you’re going to get cancer, but your actions are giving you cancer. That’s a lot of stress and shame combined. That’s the kind of OCD I’ve had for years." That anxiety informs If the Raindrops United. Friedlander always enjoyed doodling as a kid, but he got more serious about it when touring as a comedian started to wear him down. “Instead of just sitting there and working on my act, because I needed a break, I just started drawing,” he said. A couple of years ago, when he had to turn down work because of debilitating vocal pain, he got nervous he’d have to stop performing altogether. “So I said, ‘Fuck it. I’m gonna start drawing cartoons. I gotta do something.’” After a while, he realized he had about 50 drawings and thought he could put them together in a single volume. His vocal problems subsided, but the drawings remained, and a book was born.
If the Raindrops United, which goes on sale October 20, is a book of satirical drawings that comment on the everyday inequality and absurdity we witness in our country, tackling everything from gentrification to the dynamics of power between the sexes. Though it's a collection of illustrations, it captures the clever way that Friedlander has successfully addressed these topics in his stand-up — visual jokes that make you think. (It's a touch more serious than his first book, a satirical guide to martial arts.) The title of the new volume comes from Friedlander's rather utopian idea that just because something is small doesn't mean it can't also have an impact. “If people came together, they could have a lot of fucking power, more than they realize,” he said. “A lot of people feel powerless, and as an individual, a lot of people are powerless. But, if people unite, accept each other, come together, and work for a common cause, nothing can stop them,” he said. This idea is cleverly illustrated on the cover, which features a Godzilla-sized raindrop falling on Manhattan. It’s right below these words from his former boss, Tina Fey: "Judah has drawn a weird and funny book in the grand '70s tradition of B. Kliban! I think this book will probably fix the world." Raindrops offers a clear sense of what's important to Friedlander. After spending time with him, I realized it's the smaller details that reveal the most. Take, for example, the small bottle of hand sanitizer he keeps in the side pocket of his jeans. “Oh yeah,” he said, chuckling, when I asked him about it. “I forgot that was in there. I can be kind of a germaphobe.” He also keeps small notes in his front pants pockets, folded up haphazardly. When he pulled them out to show me how "unorganized" he is, it was like looking at the innards of a distracted middle schooler’s backpack. They were mainly set lists, notes jotted down but not yet fleshed out. “See, this one fell apart,” he said, pointing to one segment of paper with a few words scrawled on it. “I’m already worried that I lost the other half of this.” (Turns out he didn’t.) “I definitely have OCD paranoia problems. That can inhibit you from doing stuff sometimes. I have trust issues with people as well. “It’s extremely stressful," he continued. "Imagine if you thought every time you tie your shoe, you fear that not only you’re going to get cancer, but your actions are giving you cancer. That’s a lot of stress and shame combined. That’s the kind of OCD I’ve had for years." That anxiety informs If the Raindrops United. Friedlander always enjoyed doodling as a kid, but he got more serious about it when touring as a comedian started to wear him down. “Instead of just sitting there and working on my act, because I needed a break, I just started drawing,” he said. A couple of years ago, when he had to turn down work because of debilitating vocal pain, he got nervous he’d have to stop performing altogether. “So I said, ‘Fuck it. I’m gonna start drawing cartoons. I gotta do something.’” After a while, he realized he had about 50 drawings and thought he could put them together in a single volume. His vocal problems subsided, but the drawings remained, and a book was born.
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We got to talking about a drawing of pubic hair that suggests women have the most power. Friedlander said it’s both a commentary on how we as a country tend to be afraid of hair as well as an analysis of how we view power itself. “I think in general, people might look at this one and think the world actually works the opposite way, [that] women don’t have any power,” he told me. “I think in many ways, in relationships and certain areas, without even knowing it, women might really have all the power.”
At least, that how he feels sometimes. His particular brand of feminism extends from the dating world to bringing people into the world. He offered, as an example, the way people tell him to ask out a woman. “Why? Why should I ask out a girl who I like? If she’s not making some kind of signals or moves to let me know she’s interested, that means she’s not fucking interested.”
And then there's procreation. “I wish I could be a woman and know what it feels like to create life. I would love to experience that. Have someone growing inside you? I can’t imagine what that would be like. I’ve had kidney stones seven times, so I’ve given birth to a few rocks.” He wasn't equating the two, he assured me. He’s just forever in awe. It's the kind of statement that probably hasn't been uttered since the '70s, but we'll take it.
He has another drawing of two scalene triangles. One is a natural scalene triangle. The other, which is more symmetric, is a “scalene triangle after corrective surgery at the Isosceles Beautification Institute.” This, Friedlander said, is a comment on body image. “You don’t have to get plastic surgery to like yourself or for other people to like you. You’re fine the way you are.”
I asked Friedlander if there were any women’s issues in particular right now that are bugging him. “The whole Planned Parenthood attack is big right now,” he said. “Certainly, in show business, if you look at directors in Hollywood, it’s still way fewer women than it should be.” He encourages putting up a fight about it. “To get any kind of change going, people have to realize that it’s never given to you. You always have to fight for it. There were never law changes for equality that politicians just offered up. Never, never. It’s always a struggle with protests and blood and tears. That’s just the way the world works, unfortunately.”
It’s not lost on Friedlander that he says all these things from the privileged standing of a white male. But, he doesn’t think it should matter all that much. “That is definitely on my mind. Like, ‘Who is he to talk about our stuff?’” he said. “I respect everyone’s opinion, whether I agree with them or not. Things are never going to get better unless everybody is helping out everybody. If the people in power aren’t doing anything, it’s just going to be a lot fucking harder. I want diversity.”
To him, the argument that being a successful comedian who's made a good living somehow disqualifies him from weighing in on big social issues is a non-starter. “And I’m like, ‘Yeah, but I can still fucking fight for what I think is right.’ That doesn’t negate you from trying to help with inequality.” Where his stand-up sets jab at things like gentrification, sexism, and gun control, If the Raindrops United punches those same issues right in the gut.
As determined as he is, he is a bit worried that some of his illustrations may upset people. A Jim Crow drawing, for one. Or another about vampires that could be misinterpreted as a stab at women. But this is what comics do: tackle the taboo. “I don’t like finding comedy in easy places,” he said. “I think laughter about serious issues, when done right, can free you up a bit to start talking about shit instead of having the elephant in the room and not fucking saying anything."
If The Raindrops United is available tomorrow. You can see Friedlander at The Comedy Cellar on Tuesday, October 20 and at the Powerhouse Arena on Wednesday, October 21.