David Wain has been making people laugh for close to two decades (and most likely longer, if we count his formative years). A founding member of The State and Stella, the funnyman is also responsible for the popular web series Wainy Days on My Damn Channel. The show returns for it’s fourth online season tomorrow, and to celebrate, Wain is bringing it live to the stage at 92YTribeca in NYC, with help from friends including Paul Rudd and longtime cohorts Michael Showalter and Michael Ian Black. We caught up with the man behind modern comedy classics Wet Hot American Summer, The Ten, and Role Models to find out what he has in store, as well as his thoughts on his original troupe’s MTV series getting the DVD release fans have been clamoring for since last century.

Flavorpill: How does it feel to finally see The State released on DVD? Were you involved in how it would be presented?

David Wain: Yes, the whole group was majorly involved in every aspect of it — making sure the picture and sound were right, all the commentary and extras, the packaging, publicity — all of it.

FP: Wainy Days has been really successful. What are the best and worst things about making a series specifically for the web? What can people expect from the new episodes?

DW: Web is great. At least in my situation, it’s all the fun part and very little of the pain-in-the-ass part.  The stakes are low, and it’s a unique opportunity to work with many great actors and other collaborators — a chance to try ideas and keep creating in between bigger projects. And My Damn Channel gives me zero notes and zero creative parameters.

FP: You’re bringing the series to the stage at the 92nd St Y in New York this week. How do you think it will translate live? Will it be similar to the live vs. video components of the Stella material?

DW: Parts of it will also be a sort of “live” version of the web show, but it’ll mostly just be a fun night of different comedy and music related to Wainy Days.  Expect a lot of surprise guests!

FP: You really seem to keep your fingers in a lot of pies — writing, directing, acting, producing, performing standup; what do you enjoy the most?

DW: I really enjoy the very idea of doing different jobs.  They’re all parts of the same whole for me.  I like being able to work on something from beginning to end.

FP: What project are you most proud of from your career so far? Which one do you wish people would forget?

DW: I’m incredibly fortunate (or delusional or narcissistic) to be able to say that I’d proudly, without qualification, present any of the major projects I’ve done (The State, Stella, Wet Hot, The Ten, Role Models, Wainy Days).  Some of the minor efforts are perhaps a little more embarrassing, most of which didn’t see the light of day.

FP: You and the Michaels (Ian Black and Showalter) have really stuck together since the State days, especially through Stella. Is it strange to see them working on a project without you (their new Comedy Central show)?

DW: Ever since The State stopped working together as a group in ‘97, various smaller groupings have been doing projects together (some are listed at the-state.com). I’ve made two movies with Ken Marino, one with Showalter, wrote a pilot with Joe LoTruglio, had everyone act in my stuff, and of course all the Stella projects with Showalter and Black.  Their new series, I think, came together during the period when they were touring together doing stand-up while I was doing Role Models.  So it was just an organic development for it to be them without me.  Maybe I’ll have a guest role or something!

FP: The recent State reunion seemed like a pretty big deal for everyone. Had there been any animosity between groups up to that point, or had you all stayed close? Speaking of which, it was great to see all the cameos in The Ten.

DW: We’re in every way a family.  We’ve had our disagreements and issues since the day we met, but we also spent nine years together 24/7 teaching each other comedy. We’ve never lost touch, and have seen each other socially and done a million projects in different configurations (see previous answer). Getting together this year and performing brand new material as the full group was great.

FP: What’s next for Stella? I saw there’s a live DVD on the way. Anything else planned? Are there any State events planned in relation to that DVD release?

DW: TBD right now, but it would be great to have some events.  Stella and The State have always been limited by everyone’s schedules.  Michael and Michael will be focused on their show this summer, but as we get into the fall/winter, hopefully we can do some touring.  We had a great tour over the holiday season this past December/January (which is when we shot the live DVD). We’re also developing an idea for a Stella movie. As for The State, maybe some more live shows like we did in San Francisco in January.

FP: Do you have any other projects in the works? Other films on the way?

DW: I’m writing the next movie right now. That’s all I can say! Plus, the new season of Wainy Days starts May 7th.

FP: You seem to enjoy working with Paul Rudd a lot. You guys have done numerous projects together. Is he just the ideal comic actor?

DW: That sounds like a silly thing to say, but, yeah, pretty much for me. We do see eye to eye on so many things, and he’s just got this ability to be funny and appealing while also being completely real. Very rare. And he’s just fun to work with!

FP: What’s the funniest thing you’ve seen lately that you haven’t been involved in?

DW: Stephen Colbert’s ad about the gay storm coming.