Dane Cook
Credit: Nick Spanos/Showtime

The mid-2000s were some pretty damn good years for Dane Cook. In ’06, the Comedy Central alum’s Retaliation became the bestselling comedy album in 28 years, going platinum; Rolling Stone named him Hot Comic of the Year. Cook was the comic messiah of frat boys.

Then in late ’07—the same year Cook became the second comedian ever to sell out at Madison Square Garden—the tides began to turn against him, as they often do. Of course, Cook always had detractors—but at some point, the loathing reached critical mass, tipping the scales of public consensus. Dane Cook-fatigue set in. Accusations of stealing jokes from the likes of Joe Rogan and Louis C.K. were hurled, and an ugly blitz of online haters ensued.

Then Cook, 42, hit a rough patch personally, too. “I lost both my mom and dad to cancer within nine months and it was brutal. I was close with them—my mom was my best friend. I took a year off in 2010, and my goal was [to] work as hard on myself as I ever have on my standup. And I’m glad I did that, because I can honestly say that I feel now very similar to how I felt before the first CD broke, which was all love.”

Troublemaker, premiering tonight on Showtime, is Cook’s first original special in five years, and the first one he produced himself. In it, he ridicules the everyday, like the role of technology in modern-day dating, using familiar tools: Full-bodied storytelling, over-the-top impersonations and exploiting the guys vs. girls mentality to great effect. Love him or hate him, there is no doubt that Troublemaker, is authentically, earnestly, lewdly Cook. “I see the sparkle in my eye again, that maybe for a minute may have been diminished by some tough days. And I think it reflects in [the special].”

We talked to Cook about the happy disaster that saved the show, his new indie psychological thriller (yes, really), hanging out with Louis C.K. and navigating the perils of the “haternet.”

ENTERTAINMENT WEEKLY: You produced and wrote Troublemaker from start to finish. What’s it been like doing it all yourself?

DANE COOK: Well first of all, I never want to work with Dane Cook again. Directing him was atrocious. He is a chore, that kid!

The production on Troublemaker is pretty pared down compared to your earlier standup shows—you shot it in the round. What inspired that?

My goal was to try to do a special that would be very true to me, true to my material, but also stylistically very different from most of what you see on television. I was watching the way people these days watch comedy, which is sometimes bootlegged through YouTube and online—comedy that isn’t particularly shot well. And yet there’s hundreds of thousands of hits on some of those pieces. I was watching a lot of old comedy specials, like early ’70s, even some early ’80s stuff. What I really liked about the style was how under-produced they were because it really feels particular to the room and the tone.

Is the ’70s inspiration why you chose Marty Callner to direct, who did two of your specials before, Vicious Circle and Isolated Incident?

I wanted Marty to direct mine in the round because he had directed [George] Carlin in the round in ’76. I thought it would be kind of a cool way to take those elements of what he did back in the day in front of a couple thousand people, and see if we could accomplish something.

You have a great rapport with the audience in the show. How much of the material on Troublemaker was planned, and how much of it was working off the crowd?

There was one show Friday and one show Saturday, and when the Friday night show started, it was kind of a disaster. For the most part you go into a show, especially when you’re recording something, feeling like, “Okay, I’m going to get 100 percent of the material out.” [But] there were technical issues, there was a timing issue. When I hit the stage, I was in my head going, “All right, this is not going to work, this is scrapped right now. I’m not going to be able to use this.” But I did the whole show, and I was a lot looser and I went off-book and had a lot of crowd interaction.

Did you go back and watch it?

When I got into the edit bay [on Saturday], my editor Matt Somerville was like, “You should really look at Friday night’s show.” I was like “No, I don’t even want to see it! Delete it, I hate it, I stunk.” And he’s like, “I don’t know man, there’s a really interesting vibe, it might be kind of what you’re looking for.” So I end up watching it.

Then I did Saturday night’s show, and that turned out to be one of the best shows that I’d done in a couple years. I would say 60% of what ended up in the special is probably taken from Friday night. It captured something that I think a lot of comedians really want to capture, which is a really present nature. So it was a happy accident, it turned out to be pretty much why the special is called Troublemaker and has the vibe that it does.

How would you describe where your brand of humor is at these days?

Well I am funnier than ever! I am the funniest I’ve ever been—that definitely helps. The special really talks a lot about the modern relationship, and tech, and some of the things that are what we use today to communicate. But my new ideas for the new special are really all about love, and really what it means to be in love… That’s definitely something tonally that I’d like to create for the next incarnation.

Dane Cook’s Romance Special?

Yeah! Dane Cook in Love or something.

Been hanging out with Louis C.K. lately?

I just saw Louis last night! We were just at the Comedy Cellar together. We’ve actually performed the last couple of weeks together on eight shows, back to back.

You played yourself on his FX show Louie last season, after the public allegations about stealing his material. How was it guest starring on his show?

That was a lot of fun. It was perfect timing after a few very bizarre years with allegations and things like that being slung left and right. For him to call and say, “Let’s put this thing to rest,” I was like, “Yeah, amen. Please.” It just was great television and I hope I get a chance to do that with him again. If not, then tonally I like that kind of stuff.

Let’s talk about that haternet—people can be pretty brutal, as you know well. How are you dealing with online haters these days?

You know it’s such a culture now! You used to get roasted sometimes at events, and now it’s like a constant kind of roasting. And yet it is a weird, twisted version of love and appreciation. It’s like SNL doing a send-up of you: It might sting at the time, but it really means that everybody’s getting you and tuning in to you. I’d rather have detractors and people spewing something from the other side than having everybody shrug and go, “Oh, you know, him. He’s all right.”

You recently executive-produced and starred in the movie 400 Days, directed by Matt Osterman, and co-starring Caity Lotz (Arrow), Ben Feldman (Mad Men) and Brandon Routh (Superman). What’s the film about?

It’s a psychological thriller—it’s gritty, it’s dark. It’s about four astronauts that go into a simulator for 400 days. There’s an event that takes place while the four of us are in there, which makes you start to question how much of a simulation this really is. This is actually based on what they’re really doing right now, preparing astronauts for long-term space-travel by putting them in these underground simulators where they live for three, four, five hundred days to just get them used to being together for what could be years of travel through space to Mars.

Who do you play?

I put about 25 lbs. of muscle to play a very intimidating astronaut who is a bit of a Jekyll and Hyde, you don’t know if I’m for the good of the mission or if I’m trying to do something dastardly. I’ve done a couple of films like this over the years, like a Mr. Brooks or even like a Dan in Real Life, where I got to show some different colors from the standup.

Last couple questions: In your special, you talk about online dating, and you mention that you have an account on Christian Mingle. True?

I deleted the account!

You also said you have a separate username for tackling online haters. Is your username still “Soul-Crusher11?”

I think they must have heard my routine, because I lost my “soul-crusher” card. I think somebody figured out it was me. I knew once I said that name on that tour, I was doomed. So I had to come up with a new hater-name.