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50,000 Monkeys at 50,000 Typewriters Can't Be Wrong

In Which I Interview Patton Oswalt for Playboy

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This is a big deal for me. A few months ago, my friend introduced me to Marc Bernardin, who is a new editor for Playboy. My friend told me that Marc is helping bring back the kind of writing that Playboy had in the 70s and 80s, when it was held up next to Esquire, Vanity Fair, and Rolling Stone. They both thought that I should become a contributor, and be part of that effort.

It was an incredible honor when Marc asked me to interview Patton Oswalt for The Playboy Conversation, and I’m really happy with how this turned out. Here’s an excerpt.

Geographically, Los Angeles isn’t that big. In fact, we say that pretty much everything, from The Valley to the South Bay is about a 20-minute drive, until you account for the traffic. It’s just past eleven in the morning, and I’m stuck on Highland, just six miles (but almost 22 minutes) away from my destination, because I didn’t account for the traffic.

I call my assistant and ask her to “let them know that I’m stuck in traffic, and I’ll be there as soon as I can.” She calls me back a few minutes later and tells me that everything’s okay. “Patton’s already there, so just drive safely and get there when you can.”

I try and fail to be patient. I can’t make the traffic move faster any more than I can go back in time to take a different route to Hollywood from The Valley, but I’m late, and the only thing I hate more than waiting for someone is making someone wait for me.

Twenty-five minutes later (parking is a bitch in Hollywood) I walk into BLD restaurant on Beverly. I look around and find Patton, sitting at a small table, facing the door, sipping from a mug while he looks at his phone.

“I’m so sorry to keep you waiting,” I say.

He looks up, cradling his mug in one hand. “It’s okay. Is everything alright?”

“Yeah,” I say, sitting down. “There was construction on Barham and an accident on the 101 and–”

“And you’re fucked,” he says.

“Pretty much,” I say. The waitress comes by and I order some coffee. I pull out my recorder, and set it on the table between us.

Where do I start? I’ve known Patton Oswalt for almost 15 years, though we’ve never been particularly close. When our orbits intersect — most frequently at Comic-Con or in the lobby of a theatre in Los Angeles — we talk for a few moments before going on our respective ways, until we meet again. I like Patton, and we’re friendly, but we’re not friends. This isn’t the first time I’ve interviewed someone, but the uncertain intimacy between us, combined with my general anxiousness about being late, has made me a little off balance. Whether he senses this or not, I don’t know, but Patton takes the pressure off.
PATTON OSWALT: So you’re interviewing me for Playboy?
WIL WHEATON: Yeah. And I’m not going to lie; I think it’s pretty cool. It’s such an interesting part of our culture. Magazines like Playboy are so different to the current generation than they were to ours. Like, if you want to look at boobs today, you just go to the internet, but when we were younger, we had to, like, actually find a magazine, find that one kid who for whatever reason, had an older brother or something who got it.
PATTON: I think I actually wrote a thing for Playboy about telling the new generation buy Playboys and go leave them in the woods, just so those kids can still, it gets them out of the house. I think I actually wrote that down for them. Gets them out of the house. Because the sense of that quest, it doesn’t really exist anymore. Not only the quest, but the currency. Now you’re the kid that has a Playboy: What can you trade for it? What can you get for it, you know?

(My friends and I hid  a Playboy in a tree, covered up with some rocks, in the wash behind our house. I remember that the playmate of the month was Hope Marie Carlton, and the Internet tells me that that means we had the July 1985 issue.) The waitress comes back, and sets a small press pot down in front of it. It probably has three cups in it. “Would you like to order some breakfast?”

I look at Patton. “Yes, I’ll have the huevos,” he says.

I order the first thing that I see on the menu. “Blueberry pancakes, with a side of bacon or sausage.”

She writes on her notepad, stops, and looks at me. “Did you want bacon or sausage?”

I notice that she has blue eyes, and is pretty. She has a cool tattoo on her left forearm. “I don’t care. You choose.” I hope I’m not being flirty. That happens sometimes when I’m nervous.


You can read the rest, where we talk about Twitter, fatherhood, stand-up comedy, The Interview, and his new book, Silver Screen Fiend, at Playboy.com (the site is probably NSFW, but the page where our conversation lives is SFW)

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6 January, 2015 Wil

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35 thoughts on “In Which I Interview Patton Oswalt for Playboy”

  1. Craig says:
    6 January, 2015 at 9:00 am

    Really enjoyed it, especially the Twitter discussion. Nice work.

  2. Charlotte A. Cavatica says:
    6 January, 2015 at 9:04 am

    “Wil Wheaton is the creator and host of Tabletop, the author of several books, and an occasional actor.”

    Something about the order of operations here really pleased me—I think because acting is usually held up as the first plaudit for a lot of your contemporaries, when it’s only one part of who they are and what they do. I tend to think of you as a writer and creator first, and I’m happy to see you billed that way more often. You definitely earned it. Nice piece.

  3. Rachael Berkey (@bookoisseur) says:
    6 January, 2015 at 9:06 am

    I also write for Marc at Playboy! He told me that the site – in front of the paywalls at least – IS SFW which I think is pretty awesome. 🙂

    1. Wil says:
      6 January, 2015 at 7:37 pm

      Cow Orker HIGH FIVE!!

    2. I8brains says:
      8 January, 2015 at 4:29 pm

      That would be a good topic: Top Playboy Interviews of All Time. On second thought, I’m certain it already exists. Everything already exists on the Interwebs.

  4. Uv says:
    6 January, 2015 at 9:17 am

    This time I can claim very truthfully: I read playboy for the articles…

  5. Ria says:
    6 January, 2015 at 9:33 am

    Very good article. Could feel you both enjoyed the talk.
    So… will we see him on TableTop next season?
    😉

  6. Jamison says:
    6 January, 2015 at 9:38 am

    Great interview. Interesting you mention PlayBoy getting back to being a source of good writing. I remember in college reading Martin Luther King Jr.’s PlayBoy interview and it was pretty phenomenal.

  7. Todd says:
    6 January, 2015 at 10:11 am

    This was a fun read. I’d love to just have a conversation with either of you guys. Talk about gaming, movies, Commodore computers… Hit me up! 😉

  8. lis says:
    6 January, 2015 at 10:27 am

    I wanted to read the thing Patton wrote about leaving Playboy for others to find, but was swarmed by popups that I couldn’t eliminate on mobile.

  9. Brian Greenberg says:
    6 January, 2015 at 10:31 am

    WWdN is one of the ways I pass the lunch hour at work, and now, in the space of two days, you’ve given us a podcast (can’t listen at work) and an interesting writing piece hosted on playboy.com (the corporate filter does not distinguish between playboy.com and ionlyreaditforthearticles.playboy.com)

    Gotta start reading this site at home too, I guess… 😉

  10. jeezusgut says:
    6 January, 2015 at 10:37 am

    I actually had a subscription to Playboy for about a year and a half wen I lived alone and it was actually for the articles and stories. I can go online and see graphic depictions of sex if I wanted to, so the sight of well lit and proportioned boobs on paper was not something I was willing to shell out money for. The high level of writing on the other hand was.

    Out of curiosity, how often are you going to be writing for Playboy?

    1. Wil says:
      6 January, 2015 at 7:36 pm

      Out of curiosity, how often are you going to be writing for Playboy?

      I’m not sure. Frequently, I hope.

      1. ICanThinkAndDoThink says:
        7 January, 2015 at 9:57 am

        Then I might start reading playboy online. I like good writing & good conversation.
        See I might get quoted out of context.
        My family comes up with this crazy~~> they know I said [this].… I really stretch my mind to track down what was said where & when (it is so twisted from what I said) or did they just pull it out of the air or maybe dream it. The Internet & other technology amplifies human failings as well as letting me read your article when I probably would not otherwise find it or go out & buy the mag. The fact is most persons are not really thinking most of the time. Following or kneejerk reacting or crafting words to get a click is not thinking. Some persons do not reveal an ability to think ever. Usually if they are not family one can avoid them face to face, sadly not always.

  11. Melissa Joulwan says:
    6 January, 2015 at 10:43 am

    Two of my favorite intelligent entertainers in one place? I’m in! Congratulations! Going to read now.

  12. Josh Neff says:
    6 January, 2015 at 11:04 am

    This is less an interview to me and more a conversation between two of my favorite people. So very, very fantastic!

  13. Jared says:
    6 January, 2015 at 12:09 pm

    I am always so impressed by your writing style and cadence. It matches my reading cadence perfectly, but there is more to my enjoyment of your writing than that. You are descriptive and eloquent without coming across as pretentious, and reading your articles and postings feels like having a conversation with an old friend that I don’t get to see very often, but whose company I enjoy immensely. Well done.

  14. J.R. says:
    6 January, 2015 at 12:23 pm

    Great job! Really enjoyed it.

  15. Chris says:
    6 January, 2015 at 12:52 pm

    Love this interview. I love interviews that are true conversations.

  16. Leslie Stockton says:
    6 January, 2015 at 2:17 pm

    You are an interesting man Mr. Wheaton. lol thank u 🙂

  17. Mike says:
    6 January, 2015 at 7:13 pm

    Please get him on tabletop! That would be amazing!

  18. Disappointed says:
    6 January, 2015 at 8:37 pm

    Great writing, but how on earth can you reconcile your stand on things like gamer’s gate and treating cosplayers with respect, and support a pornographic publication?

    1. MrGenre (@MrGenre) says:
      8 January, 2015 at 1:37 am

      Agreed. Love you, Wil, and I totally respect and understand the want to resurrect a lost literary tradition, but this is not worth it in my opinion. At the end of the day, they asked you to do this to cater to a shared audience of readers, not further some public good. There are a lot of wonderful childhood traditions that should be resurrected, but finding your Dad’s stash of dirty magazines isn’t one of them. My son will find a bunch of copies of Wired and a clean browser history. Pornography hurts both the men who read it and the women it objectifies.

      That said, I loved the first part of the interview. Too bad I won’t read the rest on its current site. Why not just host a series of interviews on your own site? Your readers have to be more worthy of this than Playboy’s.

  19. A says:
    6 January, 2015 at 9:45 pm

    At first I saw “When our bits intersect.” Stupid brain! Funny, but stupid.

  20. Danielle Courtney says:
    7 January, 2015 at 6:37 am

    Awesome interview. Patton Oswalt is one of my very favorite people. Well done, Wil!

  21. J says:
    7 January, 2015 at 7:17 am

    Seriously, Patton Oswalt needs to be on Tabletop or the RPG show. He is a big D&D nerd.

  22. jannasilverstein says:
    7 January, 2015 at 7:30 am

    Nice work, Wil. Really enjoyed reading the piece.

  23. Justin says:
    7 January, 2015 at 9:35 am

    The reason I want to pick up the Playboy issue is for the article written by Wil Wheaton. Hmm… I don’t think the wife is going to buy that line (even if it’s true).

  24. See email address says:
    7 January, 2015 at 11:18 am

    Censoring comments critical of the double standard is interesting. Original comment was how can you reconcile a pro equality stand on things like cosplay and gamers gate, yet support objectification and pornography?

  25. Dad says:
    8 January, 2015 at 7:23 am

    Great interview. I, too, would like to see him on Tabletop. But, it seems he is a very busy man.

    In reference to the Gamer’s Gate and cosplay issues and Wil writing for Playboy. The majority of the women in this publication are involved by choice. If a women poses for Playboy she knows she will likely be objectified and that it is primarily the intent of those women and the magazine. I don’t think these women are unaware of what comes with posing nude in the magazine.The mistreated females in Gamer’s Gate and at cons are not asking to be treated differently, they just want to be treated like real people with real worth. Because they are real people with real worth, you know.

    My apologies if anything I said gets misinterpreted. I am not the best at conveying what I mean. But, I feel very strongly about this equal treatment issue. As a dad trying to teach my son that it’s okay to like My Little Pony and dance. And teach my daughter that she could be the one to beat Bowser and save Mario from the castle because girls can be brave too.

  26. Wil Knoble says:
    8 January, 2015 at 3:34 pm

    I just came in from snowplowing my long driveway and while the wind threw dusted cold into the recesses of my hood, I suddenly felt like Private Nobody on Hoth, clearing the hangar for incoming snowspeeders. After pealing off my jacket and shaking what looked like powdered sugar out of my coat pockets, I jumped in the bathroom for a quick but hot shower. Afterwards I sat down at the computer with a cup of coffee (gotta get it in me before 6 or I’m up all night) I needed something to help me relax. Wil, reading this article was my chocolate chip cookie I was missing to go with the coffee. I want to say how much I like your writing, but I don’t know how to express appreciation “online” and not sound like an ass-kisser…I don’t care for ass-kissers…and if I hear and ass-kisser, it makes me frown and want to sit in a recliner so I can throw the foot-rest up with a hard jerk, like Archie Bunker would do to show is distaste with a non-vocal but quiet purpose. Your blog is one of less than a dozen sites I check daily and the amount of goodness I’ve read spurned me to finally say “I’d buy that for a dollar!” Best wishes and continued success.

    Wil from Wisconsin.

    1. Wil Knoble says:
      8 January, 2015 at 8:16 pm

      *Edit – Not spurned…spurred…hiya!

  27. Karen Ellison says:
    11 January, 2015 at 6:20 am

    My husband and I subscribe to Playboy. I’m excited about reading your article!

    What’s funny is that whenever a new issue arrives, I totally hog it until I’m done reading the articles and then I’m like, “Here ya go, there’s boobs in this, lol.”

    We actually both do read it, and we think the funniest
    part is Playboy Advisor. People write in about the weirdest things!

  28. Josh says:
    15 January, 2015 at 4:53 pm

    Really dug the interview — great job. Is there a secret to knowing what are the “right” questions to ask?

    1. Wil says:
      15 January, 2015 at 5:27 pm

      Is there a secret to knowing what are the “right” questions to ask?

      Sort of, I think? Because I’ve been on both sides of the table, I know certain things that work and don’t. When I’m giving an interview, it’s always to support something, and I want to talk about that thing. I don’t want to talk about something like TNG, usually, because there just isn’t anything new to say after 28 years.

      I think about the stuff that I want to know, and the things that the interview subject is interested in, then I take my experiences as an interviewee, and put all that stuff together into building a short list of “do not forget to ask” questions.

      I also think it’s really important to listen, let the subject talk and express themselves, and ask follow up questions.

      I think a lot of it is just feel and experience, with a few rules that help make it work more often than not.

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