You see Kevin Pollak pop up in the most unexpected of places. First, he’s a hilarious stand-up, then he’s on the couch with Johnny Carson and Jay Leno doing spot-on impressions of Peter Falk and Christopher Walken, then he’s standing next to Tom Cruise in A Few Good Men. Pollak definitely hasn’t had a standard career trajectory, but it seems that suits him just fine. Recently, he ended a recurring role on the Chuck Lorre sitcom Mom. For the last six years, he’s hosted the popular video podcast Kevin Pollak’s Chat Show, where he has had in-depth conversations with just about everyone he’s worked with, and he leans on that Rolodex and those interview skills to direct a documentary called Misery Loves Comedy, which is already available on iTunes and Video On Demand and will be released in theaters on April 24. In the movie, he talks to everyone from Freddie Prinze, Jr. to Jimmy Fallon to Opie and Anthony about what led them into comedy, and the miseries they suffered along the way.

You know how sometimes people say when you talk about comedy it takes all the fun out of it? When you decided to make the movie how did you decide to do it so it didn’t sound like people just prattling on about the minutiae of comedy?
I wanted them to talk about the minutiae of themselves. I’ve known funny people my whole life and I chose this cast very carefully in the sense that I knew even when they were talking about the most unfunny thing they couldn’t help but be funny. So while the subject matter is not necessarily misery, throughout the film they’re talking about the journey that led them to find a way to overcome misery — like the case of Maria Bamford; her honesty of sharing time of being in a psych ward, and then finding a hilarious way to talk about it on stage. So my hope was answered. You’re right in the sense there’s nothing more boring than talking about why something is funny, but I knew we were not going to do that. I knew we were going to get unfairly funny people talk about their struggles, and their lives, and they couldn’t help but be funny doing it.

Did you get the idea because you were doing a podcast for so long and doing all these long form interviews?
[The film] was not my original concept. There’s no question The Chat Show was one of the key reasons I was asked to direct it and there’s no reason to argue against the notion that my experience of five years of interviewing people and getting them to be comfortable helped. If you’re going to do a late-night talk show you just have to be entertaining for six minutes or 12, if you get two segments. But The Chat Show taught me how to have long-form actual conversations. So I spent about an hour with each of the people in the film on average, which is enough time to really break their spirit and get them to speak honestly and openly about anything.

How long did it take to sift through 50 or 60 hours of interviews to get it down to an hour and a half movie?
That really was the Herculean task, no question. As we were shooting people would then continue to say yes [to new interview subjects], and as they said yes we just kept slotting them in, and by the end of it we had 60-plus that we got on camera. Now I’ve got 60 to 70 hours of interviews and no script, no story, no narrative, and a similarity in question lines. [After] six to eight months of editing, maybe as long as ten months when all was told…every time I looked at a cut I would get bored with it within two viewings. And because there was no script to follow I could change the order of anything and everything, and unfortunately that means I could edit until the end of time. Thankfully, that end of time came with the deadline to submit to Sundance.

What got left on the cutting room floor that you really, really wish made it into the movie?
Oh, all kinds of stuff to be honest with you. I mean it’s literally endless what was left behind, and it’s difficult for me to even conjure memories of it because it just kept happening. So maybe it’s still too painful; it’s been a year. It’s been long enough now that you would think I’d be over it, but I’m not.

Who surprised you with their blunt honesty?
Well Maria Bamford talking about being in a psych ward and how standup comedy became this incredible tool of recovery. Freddie Prinze Jr. talking about his dad [who committed suicide] for the very first time on camera. There’s at least a half hour more of him that I wish was in the film. Jim Jefferies being incredibly funny and insightful, and then also he has one of my favorite moments when he talks about that ridiculous family who spins basketballs on unicycles and says, “That had to have been one person’s passion.” That kills me more than anything, but then he talks about himself being clinically depressed and suicidal at times. I don’t think we saw that coming. Or a moment where Bobby Cannavale, who knows what it means to feel naked and vulnerable, and I also knew that he was a hysterical character who doesn’t mind sharing his own misery. Judd Apatow talking not only about his childhood trauma over never getting picked, but also as an adult having success as a director and still not finding happiness. How he now realizes he got into doing of it, in the shooting and the editing, and is now desperate to find happiness in doing nothing. And he shares that he’s failed miserably at that.

Instead of it just being wall-to-wall standup comedians, what made you decide to reach out to the Bobby Cannavales of the world, the William H. Macys?
The premise that you have to be miserable to be funny is the hook, and I really wanted to find out who these people are. So when I started to think in terms of the journey that I’m fascinated by I started thinking in terms of, and I say this in the film to some degree, the children suffer from “hey look at me” disease because they’re children they want attention. Adults clearly still suffer from “hey look at me” disease. otherwise Facebook is not a multibillion dollar company. So we’re all craving and dying for attention, but who then chooses that as a profession? Who then devotes their life to the endless pursuit of vulnerable pursuit of laughter from total strangers? I mean that’s a sickness in itself. That’s a form of insanity if you really stop for a moment and analyze it, and so I knew it was beyond just standup comedians. I knew that in the case of Sam Rockwell, and William H. Macy, and Bobby Cannavale they had been on stage and had been naked as actors on stage. I saw Sam Rockwell do a monologue standing alone on stage in a Martin McDonagh play, A Behanding in Spokane, with my hero Christopher Walken, but I knew Sam stood there alone and had to elicit laughter.

How do you push past the common thought that all standup comedians are miserable?
Well Marc Maron even comments on that exact point, which is once comedians got on stage and started talking honestly about who they were and what they felt, the general conception was these guys are miserable because they were simply speaking the truth. Even when Seinfeld talked about the missing sock from the dryer he’s talking about a moment of misery that the whole audience goes, “Oh fuck, where is that sock?” Right? So it isn’t so much that they’re all miserable people, but they found out a way to articulate a common universal life misery that everyone suffers. I think that’s the masterful art form: How to craft stories, be it personal or universal, that are entertaining. That was one of the goals of the film. I tried to make that universal in the film by showing where these people came from. I wanted to get a sense of who the hell these people were and what supporter didn’t they have along the way so that by the time they answer the question “Do you have to be miserable to be funny?” we already kind of know the answer. And the very end of the film when I ask Marc Maron, “Do you have to be miserable to be funny?” he says, “I don’t think so. I don’t think you do.” And it’s clear he’s been miserable for 90 minutes prior.

You dedicated the film to Robin Williams. What stage of making this movie were you in when you heard about his death?
I was in the editing process. We were a good four or five months after shooting, and during shooting I booked everyone so whoever I could get is who we got. During those four weeks I was on the phone on two different occasions with Robin for about an hour each time and we had known each other since the late ‘70s having started out in San Francisco; he a few years ahead of me, but had been a friend, and a supporter, and mentor at various times. And on the phone when we spoke it was him kind of realizing he wasn’t going to get a chance to be in the film because he was shooting his television show annoyingly, ironically titled The Crazy Ones and he was doing 12-, 14-hour days, five days a week, and there was just no time. Literally, no time.

How did that impact how you saw the footage from there on out?
Well it specifically impacted it in only one beat. Every cut of the film there was an early moment when Jim Gaffigan said off the cuff, “All you’d really need is for one of these comedians to die and you’ve got a marketing tool.” I had to remove that beat because it was just too close to home.

How did it affect you personally?
It affected the conversation for sure. I mean those people who knew Robin well knew he had suffered from a version of clinical depression his whole life. So it affected the conversation because it became public knowledge in a much deeper and more profound way, in a shocking way because he had created nothing but happiness for everyone throughout his career, and the majority of his fans and public were 100 percent in the dark about him suffering from any unhappiness, let alone actual depression. So yeah it affected the conversation extremely.

What’s the favorite mistake that you’ve ever made? When I was asked to do The Tonight Show as a standup the very first time. Jim McCawley, the gate keeper on The Tonight Show all through the '70s, '80s, and '90s, asked me to do it and after waiting my whole life for the question I had the gall and ridiculousness in my mid-20s to say to him that I knew I would have a greater impact by sitting on the couch [next to Carson]. I knew there was a protocol: He couldn’t bring me to the couch unless I had a TV show or a movie. He was just offering me a standup spot, but I said, “I’m willing to wait until I have a TV show or a movie where you can justify bringing me out because I know when I sit next to Carson and do Peter Falk for the first time he will lose his shit.“ And Jim McCawley said, “Well no one’s ever said that to me before, so sure let’s see how long you can wait. It’s not bad for us, you’re just going to get better at this. Do you have a TV show or a movie coming out soon?” And I said no, and the truth was I didn’t even have any auditions for a TV show or a movie. I just had a childhood fantasy in that flash moment become an adult reality. It took about 14 months. I had done a Ron Howard film, Carson introduced me, I came out from the curtain, sat right next to him, and I did my Falk. He pushed himself away from the desk, clutching his chest from laughing so hard. He had me back on the show two, three times a year until he retired — it was the greatest outcome of a ridiculous, ridiculous choice I had made.

Joel Keller is one of the cofounders of the site Antenna Free TV and cohosts the weekly AFT Podcast. He was editor-in-chief of the now-defunct TV Squad, and since those heady days, he’s written about TV and other topics for The New York Times, The A.V. Club,, Fast Company’s Co.Create, Vulture, Parade, Indiewire and elsewhere.