Points in Case recently turned ten, a momentous occasion that may or may not have caused revolutions in Tunisia, Egypt and Algeria. As the site's longest running columnist (I did a 5K last year) I took it upon myself to interview Fearless Editor Court "That Bitch Better Not Be Ovulating" Sullivan and give you, the dear PIC readers, a glimpse into the man behind the magic behind the screen that dares to drip dreams. It's been a long ride for Old Sully and I continue to be very jealous of his sleep schedule, means of support, and the fact that he does not, for you or anyone else, ever have to put on pants.

Anyway, the interview took a while because we have lives, people (beer), and Court Sullivan is a very reflective (beer) human being, and we have a hard time getting our schedules to mesh (he starts drinking when I go to bed).

But we got it done.

As the man says, ten years is a long time, and it really would be a shame to finish this party off without letting the birthday boy get a slice of cake.

Writing an advice column as Court the Deer was probably when I committed to comedy as a career. It's hard telling potential employers that your last gig was impersonating a deer online.I'd apologize for the length of this column, but years of writing for this site have made me essentially immune to your fucking problems, cry-babies.

Nathan DeGraaf: Well, it's almost noon. Time to email Sully and see if he's up. I think that the best way to begin any interview is to ask the following question: Dude, you awake yet?

Court Sullivan: He is risen! Oh, is it too early for a Jesus joke? No, I'd say it's very timely. I actually thought I wasn't going to get the first email from you until around 5:30 or 6pm, but I should've known that the workday pretty much grinds to a halt for you right before lunch, when you initiate more aggressive flirtation with your secretary. But hey, you'll be pleased to know that I've dressed in my finest vintage, polyester thrift store pajamas for the interview. Or maybe you won't, you'd have to take my word for it anyway. I've also showered, but that's less important.

Nathan: So dude, when exactly was PIC born? And how did it start? Was it an email list? Take us back. Tell us the origin story.

Court: PIC was born in October 1999, two months after I started college at Emory. The original concept was inspired by another college life email column I had been forwarded a couple of times called "Ruminations" by Aaron Karo. His stuff was funny, but I felt like I had at least as many college observations after just a couple of months, and I wanted to make them quirkier and more creative comedically. So like any great new invention, I ripped off the format completely and tried to make it my own somehow. Initially, I typed up new issues, printed them out, and taped them to the inside of bathroom stalls in my dorm. Then I started taping them to shitter doors all over campus. Then I realized some people actually read when they're NOT shitting, so I started an email list after a few months, and it grew to 15,000 subscribers or so over the next 4 years of college. Oh, and I started this little website called Pointsincase.com in December 2000. NBD

Nathan: Now I've heard rumors that shortly after you graduated college, you started this business from your parents' house. Were you literally blogging from your parents' basement? What was it like back at home and explaining to your rather academically adept parents that you were starting a comedy site on the interwebs?

Court Sullivan in Halloween costumeCourt: I believe the initial reaction from my parents was concern that I was actually a drug dealer. And of course, I always played up the porn rumor whenever people heard "yeah, he runs a website." But no, it wasn't a literal basement; the house I grew up in was a sustainable-living-conscious one story. It was nice to be free from having to worry about typical initial "real world" bills like rent, utilities, and occasionally food. I would hole up in my room for days at a time, just letting creative business ideas take hold and acting on them immediately. That's the beauty of the web, too: I never have to run things by the quality assurance department, it's just a big comedy experiment. My parents were very supportive, but I don't think they realized how serious things were until they saw me broadcasting live from my bedroom on the Yahoo homepage in 2004. And by serious, I mean stuffing 34 cookies in my mouth and throwing pies in my face.

Nathan: That sounds serious. It really takes dedication to abuse desserts like that.

When you launched the site, did it start out as just you or did you have a group of writers in mind? How did you find the people who helped you make that first year happen? How long was the site around before you realized, wait a minute, I can make a living off this?

Court: I'm a pretty slow, perfectionist style writer, so when a fraternity brother of mine asked if I wanted to publish his comedy article on PIC in 2001 or so, it kind of dawned on me that I should probably start getting some help if I didn't want the site to end up collecting dust for weeks at a time. For the first few years, in addition to writing articles and other stuff like AIM Convos, I would also feature articles by random fans-turned-contributors. I really appreciated being able to diversify the voices on PIC while keeping the "comedy is king" mentality. In 2004, I had gotten to know a group of five awesome writers (AIM played a big part) who wanted to kick off the "regularly scheduled programming" phase of the site. I even wrote a column as Court the Deer, a big buck whitetail who gives overly-optimistic advice to college kids. That's still the most absurd thing I've ever taken seriously in my life, but it's probably when I decided I was committed to comedy as a career. It's hard telling potential employers that your last gig was impersonating a deer online.

Nathan: Okay, so it's pretty clear now what you've done and how you did it, but as you once wrote, on the internet, evolution happens at a thousand-times faster than in real life. Where do you see the future of internet comedy going, and as a result, where do you see the future of PIC going?

Court: "We headed into SPACE, nigga!" Sorry, that was my best Dave Chappelle impression. Clearly it would've worked better in a video interview.

I think the buzz right now is that the future of internet comedy is video. But does that always make it internet comedy? If I watch a comedian do a set on YouTube, is that internet comedy? Or does he have to be performing to a lone camera in an empty room, with intent to distribute online only? There will always be new comedy mashup formulas (think Zach Galifinakis' Between Two Ferns: celebrity + amateur video = comedy, Texts from Last Night: cell phone + text = comedy, or I Can Haz Cheezburger: picture + catption = comedy), but you have to know your strength and make that the core of your delivery. In PIC's case (wow, that's almost like saying PIN number), the delivery is text, and the medium has been anything from AIM (fake bot chats) to Twitter (140-character jokes).

I don't think I'm as worried as you are about doing the same jokes again. Maybe it's because I have a bad memory, maybe it's because I find the same shit funny over and over.Unlike "the future of" other things, comedy isn't something that gets better or more efficient over time; it constantly reinvents itself to stay relevant. The trick for PIC is to remain accessible (technically) yet flexible (creatively). I'm not social media gonzo, but I think services like Facebook will not only continue to bring PIC to its niche audience, but perhaps even draw that audience into the script itself. For instance, what if you could drop a layer on top of an article showing reader annotations, remixed jokes, or exactly which lines got a laugh? I still love the "old school" concept of hypertext in which the reader is free to jump around non-linearly in a network based on nothing more than impulse, so the future still holds 3-6 links per PIC article to other PIC articles.

Nathan: Yeah, I think it would be cooler if you went into space.

As per the re-making yourself to stay relevant thing, I think that's the hardest thing to do with comedy. When I first started writing for this site, I just dumped every narcissistic, get-me-laid-now feeling into each column and joke, but as I aged, I changed and I realized that I had to find a way to a) avoid repeating myself and b) work those changes into a different kind of humor. Hence the "I am really boring" style columns that have been popping up.

I guess what I'm asking here is: how do you see comedy itself changing to become more relevant as the world consistently gets smaller and more information becomes readily available. I mean, one of the things about comedy is that all the jokes have already been done. How do you avoid doing them again?

Court Sullivan and Bobcat Goldthwait
Court and Bobcat Goldthwait at Laughing Skull Lounge.
Court: You write them differently, put them in a new context, structure them in a creative way, etc. When I say that comedy constantly reinvents itself to stay relevant, I don't mean that the fundamental reasons we laugh changes, just that the jokes and concepts must stay fresh in order not to bring our gut laughter down to chuckles and grins. I don't think I'm as worried as you are about doing the same jokes again. Maybe it's because I have a bad memory, maybe it's because I find the same shit funny over and over. There have been plenty of articles on PIC for instance that make fun of the same thing, yet read nothing alike. Jim Carrey's recent "Black Swan" sketch on SNL incorporated all his familiar wackiness from SNLs past, but in an updated reference, and with new style (how the sketch opens and closes with him posing his face like the movie poster). Similarly (and I don't mean to compare you directly to Jim Carrey), I'm sure there are plenty of people who wouldn't mind if you continued writing narcissistic, get-me-laid-now style columns that a) didn't (quite) repeat themselves and b) incorporated new styles of humor. But on an individual writer level, that kind of evolution is going to vary greatly. Some people are going to have to move away from the same subjects or format to stay funny, or at least keep from going insane.

Also, the world is getting smaller? I've been misinformed.

Nathan: Oh yeah, the world is shrinking something fierce. Al Gore says it has something to do with the environment and him not getting elected.

Okay, now that we've got the past, present and future of PIC out of the way, it's time to tell stories. You've been running this show since before there even was a show and yet you did not write your own "What PIC means to me" piece. And that simply will not stand. So before we wrap up this here interview, I just have to know the following pieces of fluff

(Mmmmm… Delicious fluff)

Rank your five favorite PIC related moments and tell me a little about them.

Do the same with your five least favorite moments (I imagine technical issues will be the highlight here).

And Court, we need to know, what does PIC mean to you?

Court: Oh man, you're really testing me here. You know my memory is underserved, but I'll do my best to conjure up something.

Least favorite moments, yes, technical crap mostly.

Redesigning and switching the site to a sustainable platform in 2008 was a huge challenge. Up to then, PIC was kind of like a DVD rental store that just found out the ending to every movie was changing, and the store was responsible for editing them—and that nobody had DVD players anymore, just Blu-Ray. Not long before the transition, there was a ridiculous moment where my web host actually told me on the phone that I might have to abandon all the content up to that point. Tons of credit goes to the late, great Dan Zembrosky, a fan and contributor to the site, who not only motivated me to take on the project, but single-handedly led the entire makeover.

I think you're very familiar with another of my least favorite moments: when my AIM screenname was mysteriously hacked and stolen in 2005. I still have a copy of the "gentlemanly" email you sent to the perpetrator, containing the lines, "I don't think I will be retaliating via computers," "you strike me as a very God fearing and respectable person," and "I hope we never have to meet."

Hmm, favorite PIC-related moments…

Court Sullivan and Nick Gaudio
Court and Gaudio in a cab in Atlanta.
Hanging out with you and other writers (Nick Gaudio, Mike Faerber, E. Mike, Mike Curtiss) and finding out that people are exactly like their writing in person has been superbly entertaining. Watching you captivate an entire touristy bar/restaurant at 1pm by reciting a really, really long poem was like finding out that Stephen King hosts local episodes of Ghost Hunters.

Taking on Chuck Norris and his blindly devoted following in the "Anti-Chuck Norris Facts" was probably my favorite long-running stunt (besides AIM Convos).

I think one of the proudest moments was when the BBC's The Graham Norton Show contacted me requesting permission to show a screenshot of one of Scott Goodyer's blog posts for their upcoming guest, Alec Baldwin. Having the site on national TV for a celeb is sorta cool (I GUESST), but here's the kicker: the punchline of the post was a nude portrait of a very hairy Mr. Baldwin sporting a chubby front and center. I'm still trying to track down video of that episode.

But my favorite moment is a recurring one, where I read a new column or article submission and think, "Wow, this is one of the funniest things I've ever read." And it happens all the time, no jizz-oke. It's really amazing to work with such hilarious writers every day.

And that's what PIC means to me: a place where all kinds of comedy writers can come together to inspire each other, showcase different styles, collaborate, and experiment with what's funny, regardless of how weird, vulgar, sappy, dorky, or whatever else "out of the mainstream" it may be. Of course, getting support and feedback from readers who put up with our shit week after week makes it all worthwhile! Just kidding, every post is comedy gold—start laughing motherfuckers.

Nathan: Because I'm a bit of a last word freak, I just want to quote myself from a post that Sully and I wrote together one drunken Tampa evening. These words are as true now as they were five years ago: "Finding out Court Sullivan is in charge of this site is like walking onto a cruise ship and learning that your captain's name is Jack Daniels."

To ten more years, Sully. Fuck, might as well make it twenty…

More PIC 10th Anniversary articles »

We're now accepting list submissions! Although we're contractually prohibited from telling you whether Santa had anything to do with that decision. Join the PIC newsletter for weekly comedy headlines. Save 10% on comedy classes at The Second City using code PIC.