I’m one of those annoying, stubborn pricks who is incapable of liking somebody or something that is hugely popular. David Cross is one of few exceptions, along with Wu-Tang Clan, pizza, and little else. His original run of the HBO sketch gem Mr. Show with Bob [Odenkirk] and David taught me to embrace and seek out unconventional humor, and it has been exciting watching him rise from his start as just another gifted writer and comedian, to getting regularly recognized by average normies who can’t name or place him, to in the past few years becoming something larger than the former category but still not so famous that he can’t throw on a hat and blend into a crowd.

Though I admire Cross’s work in almost everything he’s done beyond that Alvin and the Chipmunks movie, I didn’t nerd out too hard or dwell on such obviously major turns like his role as Tobias Fünke in the iconic twisted tube smash Arrested Development. I managed to pitch one question about Hits, the underrated yet outstanding 2014 film he both wrote and directed, but otherwise I mostly used our limited allotted time to rap about his latest stand-up outing and to play the pandering pathetic fanboy that I am.

I have interviewed Cross several times before, and he never gets less awkward in the company of compliments. Thinking back on our most recent chat ahead of this week’s Wilbur show, I think the true humility beneath his hipster dick facade and Hollywood credentials may be part of what compels so many of his longtime diehards to stick with him through such significant stardom.

This tour looks pretty brutal. Not exactly a short jaunt between acting gigs. What kind of preparation goes into this? And how much is the show the same from night to night and city to city?

This is the quickest I have turned around and done another tour. I didn’t have a ton of material, so what I did differently is booked a shit-ton of shows starting at the end of January to get ready and work on material. As opposed to every other time [when] I’ve had five years between tours and I would over those five years accrue all of this various material I could pull from … this time I had to actually go and write it. In the beginning it was all over the place, but it really started to shape up about a month ago.

To answer the second part, it will definitely vary from night to night, just because of my approach to stand-up, it’s very loose. I know what I’m doing, but I have a tendency to riff and go down these kind of little paths that I wasn’t planning on. Which is why I have a setlist on stage with me. …  

I assume that as you have gained fans as an actor, your comedy fanbase has grown, you’ve done larger venues, etc. Do you basically have one fanbase at this point? Or are your Mr. Show and stand-up followers still a different breed at this point?

It’s a mix of people, but I certainly have my hardcore stand-up fans who come to multiple shows. Just as I was doing all these shows in New York, I noticed people coming to five different shows. There will always be a mix, and it was certainly evidenced by the last tour I did, where there were people who aren’t all that familiar with my stand-up stuff. Half of the cities are smaller towns. Boston’s going to have a more kind of sophisticated fanbase, and for some other places it’s an opportunity to go see a stand-up you’re familiar with and you liked their stuff in the movies. You may not know the stand-up, but it’s cool and it’s coming to your town and they don’t get a whole lot of people coming through there. Let’s make it a date night.

Am I right to assume that when you made Hits, you were hardly able to imagine how much more social media could drive us insane? Would you have made any part of that film differently knowing what you know today?

I just wouldn’t even … it would be a different movie. It’s amazing how much things are completely different. The turn in Hits at the end, when Dave is revealed to be this Alex Jones-loving guy, that was before the Bundy ranch thing happened. I think it might have been within two weeks of our premiering at Sundance that Sean Hannity was interviewing [gadfly rancher Cliven Bundy] and he was like, [“The negro … are they better off as slaves, picking cotton and having a family life and doing things, or are they better off under government subsidy?”] And it was like, Whoa, back it up. And this guy who was their hero that they were all behind turned out to be this racist guy. That was a little vindicating but yeah, it’s almost cute now. It’s this antiquated thing that shows you how much innocence we’ve lost in just a number of years.

What are you reading these days? What’s your diet?

I’ll tell you what’s on my little [browser] here. … You’ve got Daily Kos, the Guardian, New York Times, Splinter, Raw Story, Talking Points Memo. Those are more of the news ones, then I got a bunch of sports shit.

Are you mostly in New York these days?

Yeah. I try not to be anywhere else. Work takes me to a lot of places, but I’m in New York if I can be.

How much does New York these days look like the New York that you spoke so much about in your comedy immediately after 9/11?

I’m much, much, much different than I was when I first moved to New York. I have a different life. I was really not in a good way, kind of excessively partying and doing all that kind of stuff. I was having fun, but it wasn’t good or healthy, physically or mentally. I have a wife and a kid now and am living in Brooklyn. As for that New York—of course a lot of it has been displaced—there are fond memories, but I’m not part of that scene anymore. I love Brooklyn, I truly love where I live, and I’m thrilled that I can bring up a human being in Brooklyn. She won’t have to have my childhood.

I have managed to get some good Boston stories out of you in past interviews. Anything else you have to share?

Boston was hugely important in my development—as important as any other aspect of it. I was there for a long time. I grew up in Atlanta, but I became an adult in Boston. I have very fond memories. It was a very creative time. We didn’t have any money—we didn’t know where our next meal was coming from.

Where were you living?

Everywhere, everywhere. Cambridge, Somerville, Back Bay, Beacon Hill, Allston.

You’re going to be here two weeks before cannabis dispensaries open. How much do you consume these days? Any general thoughts on commercial marijuana? Are you excited?

Just that it’s about time. It’s way overdue. I don’t really smoke a lot anymore. I don’t handle it as well and I have way more responsibilities than I used to plus things that I want to get done in my life. I will say that on my last tour, going through somewhere in Colorado, and I was so excited for legalized weed. We went to one of these dispensaries, and you have to go through this security thing, then down an elevator. … It’s the future, but as imagined in the 1980s. It’s all white and there are all these security guards, and they’re in these vaguely Logan’s Run-ish outfits. I bought some stuff and was so excited by the idea that it didn’t occur to me for about 30 minutes that I just paid taxes on weed that was more expensive than in New York, where I just call a guy and he brings it to me. What am I so fucking thrilled about? That thrill quickly went away, but it’s about time that people don’t have their lives ruined for smoking weed.

OH COME ON. SUN 6.17. WILBUR THEATRE, 246 TREMONT ST., BOSTON. THEWILBUR.COM