Kevin Pollack is a man of many talents. He is a gifted actor, comedian and impressionist and most recently, he has added “documentary filmmaker” to that list of professions. His new film Misery Loves Comedy is an intriguing examination of comedians and the darkness that often accompanies the job. In the film, Pollack serves as an interviewer, asking probing questions with some of the entertainment industry’s leading jokesters. I recently caught up with Mr. Pollack and sat down with the talented funny man to find out more about the film and what it means to comedians this day an age. Here’s how the interview went:

Let me get this out of the way before the questions start because it’s really cool. Yesterday, when I was, and you’ll appreciate this as you are a man of chance I know from having seen you at the World Series of Poker. Yesterday when I was informed that the interview would be in room 208, I happened to be on the lotto line, playing my numbers.

Kevin Pollack: Sure, sure.

So I said, “Give me a dollar on 208.” So last night, 208 came out, so I won five hundred dollars.

Kevin Pollack: No, you didn’t.

Yes, I did! So if you’re still a cigar smoker, thank you very much.

KP: (Laughs) Listen, you had the thought and the fortitude to make the wager based on such a ridiculous thing, so the fact that I would benefit-

It’s good luck to share the wealth.

KP: You’re not wrong.

It makes you hit, so tonight, if anyone’s listening, you have to play 500 because I won five hundred dollars. That’s the logic.

KP: Not a gambler. I thank you for that. I’m very sorry that you didn’t win more.

Well, had I, if I had more singles on me, I may have put two, three dollars on that. I only had one single left. I’d already put four dollars worth, I had a five dollar bill, and I looked at this email, it said room 208, and so you know what? Give me a dollar on 208.

KP: No brainer!

Which also happens to be James Dean’s birthday, February 8.

KP: Okay, now you’re drifting. (laughs)

Yeah, I’m a little too obsessed.

KP: You did great and I thank you. The rest of you have nothing to offer? (laughs) Any gifts?

Because I know we want to talk about Misery Loves Comedy, but-

KP: Not necessarily!

I’m old enough to have remembered you from Comedy Break where the funniest sketch in the world was-

KP: How old could you possibly be?

47.

KP: Well, that makes sense.

So I was in Love Track. Was that your first Shatner, was that your first-

KP: No, I had done Shatner before.

That was really funny.

KP: It was a strip five-night-a-week show, they called them strip shows and they ran five nights a week. Sketch shows.

Yeah, sketch comedy.

KP: Mac and Jamie, yeah.

Are they still around, those guys?

KP: Technically.

Speaking of sketch shows and comedy, I’m gonna go, not further than that, but 1993.

KP: Sure.

Wayne’s World 2.

KP: Alright.

Great cameo.

KP: Thank you.

Loved it, that was so good.

KP: Appreciate that. Your turn. (Laughs) No, we can jump into questions about the film, or whatever you want to talk about.

Well, I’ll start. (laughs) Considering your-

KP: Wait a second, ladies first.

Okay, I guess I’ll start with, I guess the first obvious question is what attracted you to make a documentary about comedy and comedians overall?

KP: The concept of the film, the concept of misery and comedians was someone else, Becky Newhall is her name. She’s one of the financiers and producers on the film. She was developing the idea of doing a documentary about stand-up comedians who specifically suffer from clinical depression. She then talked to a guy who was my producing partner at the time Burton Richie, and still is. He and I had been developing a script of mine for me to direct, but when those two spoke and Becky shared the idea along with the title, which was hers, Misery Loves Comedy. He, because of his knowledge that I wanted to direct but also because he knew I had been booking the talent for and honing interview skills for five years from my internet talk show, along with my desires to direct a film, but also that I had been in stand-up for my entire life. It all sort of made sense that I might be the one to sort of guide this into the next phase. It made sense to them, and it made sense to me. It was their idea and then quite easy for me to run with it at that point, but the genesis was there.

What was it like putting together such an impressive roster of comedians?

KP: Yes, booking the talent, for any filmmakers out there who are wondering how to get famous people to be in their movie, I would simply suggest that you don’t pay them. That is the best way to get them because then you don’t have to deal with agents or managers or lawyers. You just get them to sign a release, and if they like you and they like the subject, then they will show up. It could be reduced to being that easy, or it could be that I went out to everyone I had spoken to while doing the Chat Show for five years and beyond, not just stand-up for people connected to choosing a life of creating funny and living and dying by the audience’s reaction, be they filmmakers or actors, not just stand-ups. And then we had to treat it like a film shoot at some point, so we had four consecutive five-days. Whoever was available was who we got, and they had to fit into those four consecutive five-day weeks or they didn’t. So we had 25 lined up before we started shooting, which I thought would be perfect and enough, and we needed an hour and a half, 25 people talking for an hour, I should be okay. Then as we were shooting, people kept saying yes, and by the end, we had over 60 people and almost 70 hours, and then it became a Herculean task to edit 70 hours into 94 minutes, which I mostly did on my own.

So many talented people who have varying levels of experience. I was wondering if there was anybody who maybe surprised you with their level of insight or had something to say that you didn’t expect coming from the source.

KP: Well, yeah. I mean, the reason John Vorhaus is given a writing credit along with me is that he helped put together some questions. That’s all the writing that was done was the questions. I wrote a shit-ton of questions, he wrote some, and we put them together, and then from that 40 or 50 questions, I could sort of create the conversation, but I had no idea what answers were coming. I just knew, again, experience from interviewing people on the Chat Show for five years, that if you do your research in terms of the Chat Show, you know, I have a research producer who treats it like a journalist would and fully researches the subject. And here I had people who had been living the subject, so I had to ask questions that would potentially elicit a conversation in areas that ultimately I want to be in the film, but whatever they chose to share, whatever level of honesty they chose to go to, to get to, was in their control, so I was constantly surprised, which would be the long answer. Constantly amazed and thrilled with the places people were able to go to and discuss.

(Two interviewers interrupt each other in asking the next question)

I hate it when you two fight. (laughs)

You know, it’s a very funny movie, but there’s like the edge of tragedy there, like when you dedicated it to Robin Williams. Did you interview him for the film or-?

KP: If I had interviewed him for the film, he would have been in the film. No, there was a case where, like many people, like I said, we had four consecutive five-day weeks to shoot, and he wasn’t available. He was shooting his TV show where he does that exact same five-day, 12, 14 hours a day on a single-camera show for those four weeks, and he just wasn’t available. We spoke on the phone twice during those four weeks, almost an hour each time, because he didn’t want to get off the phone. He wanted to keep talking about the subject matter and what it meant to him, what it meant to me, what he thought this film could be. You know, he had been a mentor of mine since I was twenty and a friend, and so when I was editing the film, he passed away, and my producers asked, “Do you want to get a little crew together and go out and interview some more comedians that maybe are already in the film and just ask them how they feel about this passing? And include it in the film because it seems germane to the subject matter and conversation.” And I felt that was too manipulative. That was too, taking advantage of a horrific situation. So dedicating the film to him just became an obvious choice, not only because of his tragic passing but more because of what he’s meant to me and what he’s meant to comedy and what he’s meant to fans of comedy, which is ultimately at the center of what the film is and hopes to be.

It’s also interesting, Mitch Hedberg had died, and you talked to his widow.

KP: Right.

And it’s just like, the film sort of is not, I’m just surprised it doesn’t deal with the real darkness of it.

KP: Real darkness of his passing?

No, no, just how dark some of the comedians can get –

KP: So the question is why did it not deal more with the death?

I mean, it’s a funny film, it’s just, I was just curious, to me, the passing of Hedberg is so tragic and then Robin Williams and stuff.

KP: Well, I had to make sure it wasn’t a biopic. I had to make sure it wasn’t about any one individual’s tragedy. I had to make sure it wasn’t about the journey into darkness for any one famous performer or a small group of famous performers but rather make it about the pursuit of comedy and the articulating of misery, which to me is a more interesting story than what caused someone to become addicted to drugs and die. I would rather speak to and listen to incredibly funny people talk about their experiences of misery and their path to finding a way to articulate it and entertain people with it so that, while I wanted to include Richard Jeni, but his family or the family member who controls his story wouldn’t allow me to. While I wanted to include, you know, Mitch Hedberg, people who had passed based on, in Richard Jeni’s case, you know, depression. Mitch Hedberg’s case was addiction, which could be linked to depression. That to me is a part of the film. That to me wasn’t what the film should just focus on. So I felt like there was more interest and entertaining, and even my ability to articulate the truth of all performers by not spending too much time on any one performer or any one cause of death. So if you have Jeffries talking and being ridiculously funny, his talking about the family of basketball-spinning unicyclists, is my favorite, well, it’s not my favorite, but it’s the funniest moment in the film, when he says, “That’s gotta be one person’s passion. There’s no way the rest of the family went, ‘Yeah, me too!’” You know, that’s, and I asked him, “Is that a bit from your act?” And he said, “No.” And then afterwards when I was editing, I said, “This moment is still in the film. You sure that wasn’t a bit from your act?” And he said, “No,” and I said, “Well, it should be! You should put that in your act because it’s crazy funny.” And he said, “No, I said it just there in the moment, and it’s in the movie, and that’s fine.” But it was him being honest about the weirdness of family that created this incredibly funny moment, and then later in the film, in the third act when we really deal with do you have to be miserable to be funny, he talks about being on anti-depressants for ten years on and off and being suicidal. So now we’ve experienced the journey with him. We’ve seen him being funny, we’ve seen him talk about influences, we have an emotional connection to him now, and when he says, to me, it’s so much more powerful when he talks about being clinically depressed, when he talks about having suicidal feelings because now we have a connection to him as a person as opposed to just focusing on that. So to me, that bigger picture to me was always a bit more fascinating.

I apologize now if I speak really quickly, but in regard to your editorial debut, did you also have some restrictions on what scenes or films you could include and what you couldn’t?

KP: What scenes and films-

I was assuming it was like 70 hours plus film that you could have used.

KP: Yeah.

So how did you choose what to use?

KP: It was an impossible Herculean task, and I don’t wish it on anybody. To have 70 hours, honestly, was ridiculous. I had an epiphany, what ended up being an epiphany. At the time, I just thought it was a good idea. Right before we started shooting the first round of footage of Freddie Prinze Jr. talking about his dad on camera for the very first time, my better half, who is the head writer for the Chat Show, has a genius level for attention to detail, so I said, “Let’s put you in front of your laptop, headphones on, and timecode synced to the sound, and while I’m doing the interviews, you take notes but take notes, specifically buzz words, key words, critic phrases, and then put the time code right next to it.” So then later, when I’m going through 70 hours of material, I have time codes and key words and phrases to refer to, which then allowed me to sort of hone in on similar key words from different people, though they’re all talking about their parents who did or didn’t support them, and then that would create a, ultimately would create a chapter, “Who’s Your Daddy And/Or Mom?” But before those chapters were created, it was just this non-linear ebb and flow with no story, no narrative, and as it grew, I realized that without a narrative of some kind or some kind of three-act structure, it would not have as much of an impact. It would not resonate. So along the way, there’s a shit ton of moments, be it depressing, insightful, hilarious, the full gambit, that no longer kept the story moving along, no longer fit into the narrative that ultimately had to be created. So are the best moments in the film, both comedically and tragically? In my opinion, yes. Anything that was anywhere near the apex of insightfulness or humor, it had to be in the film. I didn’t want to leave what I thought was the best parts of the movie out, but there are hours of what I would still consider to be provocative or hilarious that I just couldn’t fit in.

DVD extras? On the DVD, deleted scenes?

KP: We’re actually thinking more in terms of a series of pieces, be they five minute, ten minute, twenty minute, what have you so that there would be ten episodes, twenty episodes, whatever, depending on the size and length that we would then offer up as just a continuance of the conversation, so that made more sense than just including random bits. And also, who buys DVDs anymore? I have friends that still collect them, for sure, and I get it. They’re amazing, but I feel like there is new ways to entertain with this additional content than just special features. I feel like that now, it doesn’t sort of, the need of the audience or the filmmaker in terms of how much more there is to offer.

Do you prefer being behind the camera or in front of the camera?

KP: I would liken that to the question I’ve been asked over the years, do I prefer as an actor comedy or drama? I prefer to do both. I prefer that I get an opportunity to do them both. Please don’t ask me to choose because it suggests I won’t be able to do the other. What came from my directorial debut was something that people are enjoying, that’s amazing. Something that the Sundance film festival deemed worthy. Was it ridiculous, the fact that Tribeca Films bought the film before it even debuted? Also ridiculous. And now, I’ve been asked to direct a comedy script that people have been developing for a couple of years. That came from the documentary’s value and/or mine as a filmmaker, so this is all such a new territory to me that I couldn’t even begin to answer, but I think my answer would be…don’t ask me to choose, I don’t want to do it!

Fair enough.

KP: They are wildly different obviously, and I do have the taste and now pretty serious appetite for. I mean, I’ve been asked to direct over the years on a couple of occasions. After The Usual Suspects came out, we all had insane street cred in the indie world and whether it was acting or writing or directing, there were a lot of opportunities suddenly. First of all, I had tremendous respect for the ridiculous task of doing everything or working with department heads, just seemed like way too much work. The actors are afforded a life whereas the filmmaker didn’t seem like they had a life at all, and it was a year of your life to a film, and that just seemed daunting. I’ve been asked to do Broadway a couple of times, and they wanted a nine month run. I can’t say the same words in the same order eight shows a week for nine months! The first three months would be the greatest experience of my life, I can’t believe it, I’m on Broadway, people give a shit, this is amazing! The next three months would be, yeah, this is pretty good, and then the third three months would be gun in my mouth every night before I went out on stage. So the notion of living with material and a project and a thing for a year, you know, I didn’t have the need and desire to be, I’m not a control freak. That seemed like a big part of the job also. But after spending nine months in the vacuum of an editing bay that I created in my dining room on my own and pushing the buttons and creating little tiny pieces and connecting moments.

So that was all you then?

KP: Well, I had a two-time Academy Award winner for visual effects, Robert Legato of Titanic and Hugo. He’s been working with Scorsese since The Aviator, doing visual effects on all his movies. He’s a genius and a pal who just happened to be on the phone when I told him I was about to do this. He said, “Let me know how I can help,” and I said, “You’ve been editing, so please edit,” and he said yes. So that allowed me to then create a ten minute sort of teaser which acted as a template. We finished, we shot September and October, and the upcoming Sundance film festival of 2014, the financers asked me for this ten minute teaser to show to other potential investors. So that was a gift because it forced us to make something and take 70 hours and somehow create 10 minutes of something. And what that was, was really fast and very rapid-fire and no real story, just one person finishing another person’s sentence, and it added up to funny and entertaining. And then he was about to direct a movie, and I had to let him go, so he showed me the basic steps on Adobe Premiere, how to use two screens and sit and create bits and bins and moments and things. And then I went off on my own and expanded the ten-minute treatment teaser originally and then eventually it got so big that I had to create chapters and again find a story and a narrative all on my own in a vacuum. And once I had cut the film in its completion half a dozen times and showed it to people and made some adjustments, I then brought in another editor Bill [inaudible] who has been editing for 20 years to help with the transitions and that aspect of it, but I really felt as though I had cut the film and learned more about that part of storytelling. Every director I ever worked with and talked to would always insist that editing was the final re-write, but as a writer, member of the Writer’s Guild since 1997, as a storyteller, be it stand-up or screenplays or whatever, I always knew it was about the editing. The editing, the editing, the rewriting, the rewriting, the rewriting, fine tuning, the honing, and that’s really what the editing process became. It was just cobble, cobble, cobble, cobble down to something palatable.

You know, your film sets out to answer the question, do you have to be miserable to be funny? But you know, since a lot of the people you interviewed are rich and famous, do you by osmosis also answer the question of does money buy happiness? I guess it doesn’t if these people, you know, have obtained a certain amount of fame, a certain amount of wealth and yet they still have these issues and maybe Robin Williams being one of them, that money obviously doesn’t buy happiness, so was that a question that-?

KP: Money buys expensive misery.

Oh! That’s a good one. I like that.

KP: The truth is the benefit of the film is that it forced me to realize and focus on the fact that misery is a human condition. It’s unavoidable, it’s the only guarantee, it should be next to taxes and death as an unavoidable thing. Every human being will suffer, so then the artist, be it a painter or a singer, songwriter, sculptor, comedian, filmmaker, we have to figure out a way to articulate either our own personal misery or, as Jim Jeffries points-oh no, not Jeffries, Steve Coogan points out in the film, tell a story that allows the audience to feel like you just shined a light on what it looks like, which means you’ve made it universal. So when Jerry Seinfeld says, “Where is the missing sock? Why can’t we find the sock?” That might be minutiae, but it is misery that he is articulating. So the comedian has to find a way to articulate either their own misery or life’s, and then that becomes the fascination to the audience that the comedian has shared their own misery or our misery through their own point of view. And so that the film tries to step back and find out who is this person that has chosen to do this and what is their misery and what is their path and what is their conclusion, more so than what is mine. When people ask, when the producers asked me to be on camera, I have great respect for Michael Moore and Morgan Spurlock, but it seems a little self-serving, quite frankly. Because the editing is my opinion. The film is my opinion. That’s how I feel about it. “You Have to be Miserable to Be Funny: The Movie.” So you hear me ask some of the questions, so you get a sense of me in the room because I didn’t want to also try to be tricky about who is asking these questions, even though it would be obvious at some point, but the idea that my opinion needed to be put forth. So there’s little tiny pieces where I say we’re not like in a shared fox hole, you know, soldiers. We’re more like snipers, going from bell tower to bell tower. You see Greg Proops’ face when you hear me say it, go from someone who is listening to someone who (snaps fingers).

Right, right, right.

KP: Snap! Has that just giant grin on his face, like he can’t believe how funny and insightful that was, so that’s as close as I get to infusing my insights into any of this.

Well, that’s enough, you know.

KP: But the purpose for that moment being in the film was his revelation of, “Holy shit!” Right? Which is ultimately only wanting the audience to feel from what any of these people are saying. So that might be the only – and then one other time, I’m talking to Lisa Kudrow, and I say how it annoys me that anyone, ours is the one profession where anyone can kind of do, should they choose, whereas you don’t see anyone at a party dabbling in dentistry, but they can kind of tell a joke. They want to. It’s the one thing that I feel diminishes the difficult nature of being good at this, is that everyone can kind of do it.

People can tell jokes, but I don’t think they can be a comedian, what it takes to do what you do.

KP: Well, that’s clearly my position as well. Yeah, but I mean, I don’t know if it is common knowledge, and even if it is, it still bothers me that ours is the one profession that people can dabble in. And I think that’s the term that I have to continue using. So anyways, those are the few moments that I felt like I needed my voice sort of heard, but for the most part, I wanted to get as many creative, hilarious, miserable people as I could, get to know them in the first two acts, and put the question to them in the third act. And the reason for getting to know them again was to have an emotional connection. I think what makes the Iron Man movie so wonderful, the first one, and creates a multi-million dollar franchise with all Marvel comic book movies, is the humor and humanity of Robert’s character, and Jon Favreau’s choice to focus on the humor and humanity. That’s what makes him charming. Otherwise, he’s a rich guy with toys. Who gives a fuck? But with the humor and humanity, you have a story that I care about, and so I just kept coming back to the humor and humanity throughout the end process and trying to create both.

You know, considering your background in comedy, which is the best, I find it very ironic that your most famous film role was in a drama, and by that, I mean A Few Good Men. So-

KP: You find it.

Well-

KP: I find it ridonkulously ironic and unfortunate. Yeah, it’s a left-hand turn that I was not planning on making. Avalon was the first noticeable film, but it was also the first dramatic work I’d ever done. I was not trained to be an actor. I’m not proud of that, just happens to be a fact. I just went on auditions. That’s what you do. If you want to be an actor, you learn how to audition.

You learn your lines.

KP: And then somebody decides you can act. So then, but after A Few Good Men and Casino and The Usual Suspects, it was over. I was a dramatic actor. And even in the case of the Grumpy Old Men movies, I’m playing straight men. It is the irony of my film career considering I came from stand-up comedy and my most honed chops would be in comedy, so that’s not lost on me in any way, shape, or form.

Well, you know, Jackie Gleason once said after doing The Hustler, he’s seen a lot of great comedians do good dramatic film work, but he’s never seen a dramatic actor do stand-up comedy. So I think that says a lot for comedic actors, so the fact that you were able to be so convincing in A Few Good Men where you are constantly angry in that movie, are you channeling your inner misery or are you just a great actor?

KP: Neither.

No, I would say great actor.

KP: No, it’s Aaron Sorkin, so you know, it’s nearly impossible to mess it up, and you’ve got Rob Reiner in his first seven-movie stretch, which is arguably one of the most impressive bodies of work by any director in terms of, seriously in terms of diversity. Each one of the seven first films were wildly different than the next or the one prior. So it’s very, very difficult, not again to be self-deprecating or take anything away from what I was able to achieve, the truth of the matter is you’d be hard-pressed to fuck that part up. My task was to hold my own against great actors, so I got to be the one that people didn’t know in that film, and that contributed. However people discover you is how they know you, so that contributed greatly to my alleged abilities and foothold. But in terms of dramatic actors being stand-up comedians, well, America’s number one fear above death is public speaking. It’s not something people are wired to do, so whether you’re a dramatic actor or a plumber, the idea of wanting to stand in front of strangers and make them laugh. It’s one of the reasons that I was so interested in doing the film and to open the story up beyond “have to be miserable” to “who are these people.” Honestly, what the fuck is the matter with them? That became much more interesting to me than just the third act.

Can you tell by looking at, you personally, watching a stand-up whether they have the ability to be a serious actor or do a comedy?

KP: Yeah, I saw Chris Rock and thought it was going to take him a long time to be believable as a dramatic actor because he spoke such great truths on-stage singularly in his own voice, that I thought it would take him some time to be able to articulate other people’s words in a dramatic way that would be believable, and I think it did take a very long time for him.

And you know with most stand-ups, say Robin Williams? He can do all kinds of things just from watching his comedy?

KP: Not always, not always, but Jim Brooks in the movie talks about Richie Prior, he still calls him Richie, being much, being a true actor and great character work as a stand-up. Yeah, I think if you’re looking for that, you could probably watch most known comedians with that question in mind and you could break it down, in a moment, right there, that’s where they show they can be an actor, or you could watch someone’s whole set. Because as a solo art form, you’re the writer, the director, the editor, the producer, the performer. You’re not taught to listen, which is all acting ultimately is, listening and reacting, so you have to listen to the audience, but you’ve created the tempo and you know where the laughs are going to be, so only you ultimately hears whether you are right, which takes it right back to being a solo endeavor. So we’re not trained as comedians to listen and to interact and to react to what everyone is saying and give an honest face, so it isn’t any comedian’s fault they are not naturally a good actor or show any potential. In my case, it was literally a fluke gift. In baseball, you would say a phenom or a natural. There was no training, as I said, so I either had the ability to be as loose and fun in front of a camera as I felt on stage in front of an audience or I didn’t. And when I finally got to work with J.T. Walsh on A Few Good Men, who was one of the great actors, and confessed to him that I don’t know what I was doing, honestly, you guys are amazing and I’m up against brilliant actors, which was certainly the case in Avalon as well a few years before, and he said, “You’re already doing a technique that people study for decades to learn which is less is more. You’re already doing less is more,” because all I wanted was to not be caught acting, and he said, “You’re already doing less is more without knowing what the hell you’re doing. All you need to learn is there is a second half to that. Less is more, and nothing is best. If you can actually do nothing in the scene and still fuck us, you win.” Which if you look at some of his work, he is the best at it. So I was just a natural.

Are there any other subjects you’d like to tackle on film documentary-style?

KP: You know, I don’t know about the documentary style. It was so hard and so much more than I bit off, and given the very, very recent opportunity to direct a comedy film is enthralling and my own sort of suspense-thriller that I wrote, that’s been developing for a while, are the next two projects that I’ll direct. Yeah, I feel like I did myself a solid by doing a documentary first for the editing experience more so than anything because that’s where the story was created, that’s where the narrative was created, and I did myself a solid by going through that horrible fire. But it is way too daunting to return to anytime soon. I feel like I may have fooled enough people this time to try to tempt fates again.

Well, job well done.

Thank you.