Michael Ian Black is a founding member of two -- TWO! -- cult comedy troupes, The State and Stella. He is also an author of books for both children and adults, and most recently, in commercials, "the Expedia Guy." Last year, he completed a national stand-up comedy tour. He is a true show biz dilettante, and he's really good at all of it.
His latest book, You're Not Doing It Right: Tales of Marriage, Sex, Death, and Other Humiliations, takes on darker, more real material. Michael writes candidly about his childhood: being raised by his gay mom and her partner, sharing a room with his ill sister, and a very touching retelling of his father's death and funeral. He has the unmitigated gall to assert that, often, marriage sucks and kids are assholes. He's also not afraid to expose, hilariously, that there are no career guarantees in show biz. You're Not Doing It Right makes you nauseated from both sadness and laughter. It's an honest book, the kind that feels like a gift.
Sarah: In You're Not Doing It Right you talk about your childhood -- particularly your mother's attempts to turn you into a sensitive male like Alan Alda. My mom was also obsessed with Alan Alda, and I never could get into him -- he just seemed so... greasy. That our moms were able to see beyond the grease is probably just a measure of what tools the men of that era must have been. One Christmas, your mom actually gives you an Easy-Bake Oven. You were devastated at the time, but did this spark a lifelong interest in the culinary arts?
Michael: No, I can't say it did. That Easy-Bake Oven was my most despised Christmas present ever because, as I say in the book, I understood that it was more than a present. It was a political cudgel. It represented something an entirely new worldview informed by her lesbianism and her discovery that all men -- with the exception of the greasy Alan Alda -- were male chauvinist pigs. Yes, I understood all of this at the age of five because that it was when my powers of perception peaked. Since then, I have understood nothing at all about women.
Sarah: After your parents' divorce, you grew up in a two-mother household -- did things ever get crafty? Did they have you doing macramé or making potholders, and if so -- did you enjoy it?
Michael: Ours was the least crafty household in the history of gayness. We made cupcakes with the Easy-Bake Oven one time, and she crocheted my brother and me each an afghan. Other than that, I can't remember her or her partner ever making anything more complicated than microwave popcorn.
Sarah: Did you have any geeky obsessions as a kid -- either for gadgets or TV shows or books -- that made you feel outside the mainstream?
Michael: Not really. I don't think I was awake for much of my childhood. I did a lot of napping. This might have been a defensive measure against encroaching depression. Until about the age of eleven or twelve, I had zero interests other than trying to steal gumballs from supermarket gumball machines. I remember spending a lot of time jamming my fingers into those suckers to try to extract free gum. I don't remember ever succeeding.
Sarah: Did you ever play Dungeons & Dragons or other role-playing games? Are there any things you liked as a kid that are now hugely popular, things maybe you were ashamed to like then, that people now enjoy shamelessly out in the open?
Michael: I did. I loved Dungeons & Dragons. Actually, not so much the actual playing as the creation of characters and the opportunity to roll twenty-sided dice. I loved those pouches of dice Dungeon Masters would trundle around, loved choosing what I was going to be: warrior, wizard, dwarf, thief. I loved the possibilities that D&D created, all of which seemed far more interesting than any possibilities I envisioned for myself. I was also aware that none of the cool kids were playing these games, although my own hopes of ever attaining coolness had been long dashed by the time I got into fantasy role playing games. Thinking about it now, I wonder whether the joy I felt in creating characters ended up informing my career choice. (I am now a professional wizard.)
Sarah: I think your mom succeeded in turning you into a sensitive 70s male, though - even in the book when you write about being a young single guy on the prowl for chicks, you still care about their feelings and worry about being a jerk. Now that you're 40 -- FORTY! -- do you love and accept your Alda-ness?
Michael: I am so much like Alan Alda it's disgusting. Worse, I admire the guy as much as -- or even more than -- my mother ever did. He's kind of an idol of mine because he managed to create this extraordinary career as a performer and writer without even being a jerk. He's been married to the same woman forever, never makes a spectacle out of himself and only killed one guy.
Sarah: What cartoons did you watch as a little kid or grown kid or now?
Michael: My absolute favorite growing up was Super Friends. The assemblage of so many mighty heroes in one place was, to me, mind-blowing. It was Superman, Batman, Wonder Woman, the Flash, Aquaman, and then sometimes Hawkman and some other, lesser heroes. Plus they had the Wonder Twins in there. I always kind of envisioned myself as a Wonder Twin. My superpower: extra mustard.
Sarah: Did you read comic books or collect anything?
Michael: When I was around ten or eleven, I started collecting old Superman comics. There was a flea market near my house that I used to go to on the weekends. You could pick up old comics there for practically nothing, because they were worth practically nothing. They were all dog-eared and stained with whatever liquids the various young people who read them before had spilled on them. I loved them.
Sarah: Are there any piece-of-crap shows, movies, bands that you like that no one else does?
Michael: My tastes in all things lean towards the arty and boring. I like sports documentaries about Scrabble players, bands that play quiet, unassuming music, and TV shows that win awards. In that way, I am an elitist snob. And proud of it. Right now I'm watching Netflix's new series Lilyhammer and trying to decide if I just mildly dislike it or actually kind of hate it.
Sarah: Any obsessive pop culture stuff you decidedly haven't connected with?
Michael: The biggest disappointment for me in nerd culture over the last decade was Battlestar Galactica. I wanted to love it, tried desperately to love it, watched many episodes in order to love it, and ended up bored and annoyed. I didn't love it.
Sarah: Do you have any geeky obsessions you're trying to get your kids into? (It is sort of fun when they like what you like, but sometimes I hate when parents do that: "My kid will listen ONLY to The Ramones," etc.)
Michael: Probably the opposite. I'm so conscious of not pushing my own agenda onto my kids that I let them walk around flaunting their terrible taste. As a result, I have become well-versed in the art of Miley Cyrus.
Sarah: As a star of two comedy troupes and their attendant TV shows -- The State and Stella -- you're a cult celebrity with a devoted cult following. What is your favorite way to be recognized in public? What is the nerdiest encounter you've ever had with a fan?
Michael: I'm trying to get better at this, but I'm so awkward when people approach me, so shy, that people often mistake it for jerkiness. It's just so embarrassing to me when people approach, particularly if I haven't shaved that day or have a huge forehead zit or something, that it's all I can do not to just flee when they say hello. I'm very introverted, so it requires a huge effort for me to put on a smile and extend a hand and accept compliments. I would much rather be insulted than complimented any day.
Sarah: As an actor, do you prefer to play a heightened version of yourself, or a completely made-up bizarro character with a wig and tics and prostheses?
Michael: It's changed over the years. I used to need the character but as I've gotten older I need it less and less. Now I prefer to play some version of myself. To approach any acting job as me just being me.
Sarah: You joke a lot on Twitter about not having a job and needing money and not being successful enough. You're Not Doing It Right is probably one of the top 5 self-deprecating book titles. On some level, though, do you ever feel pretty good about what you've accomplished? Do you think insecurity is a necessary companion to ambition? The older I get, the more I sort of admire ambitious untalented a-holes.
Michael: This is another thing I'm working on, trying not to be too self-deprecating because I think I sometimes come off as just being unappreciative. I'm not. If anything, I grow more and more appreciative of what I have and who I am. Professionally speaking, I never take for granted that I've been able to make a living doing something I thought unimaginable when I was younger. I always said I was going to be an actor, but part of me never believed it was possible. Part of me never thought I'd be able to write a book. Or be a stand-up comedian. And I certainly wasn't sure I could be a good husband and father. If I put myself down a lot, it's reflexive. It's both because I'm afraid of what I might lose and because I'm afraid that other people will be like, "That guy's so full of himself" when, truthfully, I'm not sure what I've done that merits bragging about. I'm grateful to have been involved in things that a small number of people feel passionately about, but the truth is, it hasn't meant that much in the wider world.
Sarah: What would it take for you to feel like "OK, I've made it in show biz?"
Michael: I don't know that I'll ever feel that way, and I don't know that I ever want to. Part of what's exciting to me about my career is the constant looking forward. Whenever I finish one project, I am looking to what's next. I'm not sure what it would mean to have "made it." Made what? Yes, right now I can make a decent living in show business, so if that's the criteria, then I've made it. But that doesn't feel that important to me. The stuff that matters to me are the new challenges. I know that sounds hokey, but it's true. Which is why I am thrilled to announce that I will be on next season's Celebrity Apprentice.
Follow Michael on twitter at @michaelianblack and buy You're Not Doing It Right at michaelianblack.net
Sarah Thyre is an actress (Strangers with Candy) and the author of the memoir Dark at the Roots. Follow her on twitter at @SarahThyre.
HuffPost Entertainment is your one-stop shop for celebrity news, hilarious late-night bits, industry and awards coverage and more — sent right to your inbox six days a week. Learn more