(More Than) 3 Questions with Stand-up Comic Chris Estrada

Once upon a time, television shows had more than a few episodes to prove their worth. Take Cheers, for example, which bombed upon its arrival in 1982 before growing to become one of the most beloved programs in history. In the case of Hulu’s This Fool, which was recently canceled after its second season, co-creator Chris Estrada was not afforded such a luxury. And that’s a real shame.

The tale of two Mexican-American cousins reconnecting while trying to operate an evolving nonprofit dedicated to helping former criminals rehabilitate, This Fool in all of its satire-meshed-with-Chicano-culture wit is still watchable on Hulu (and well worth it, as it’s brilliant). Still, it’s hard not to miss its characters, especially Estrada’s acerbic Julio, stand-up Frankie Quiñones’ earnest and out-of-touch Luis and Michael Imperioli’s tortured yet humanistic Minister Payne.

What we can do by way of mourning is to check out Estrada’s upcoming headline performance at the CloudTop Comedy Festival (various times and locations Thursday May 9 through Sunday, May 12. $15-$150. cloudtopcomedy.com). We spoke with Estrada about the show, his comedy and his love of punk rock in the lead-up to the fest. This interview has been edited for clarity and concision.

Let’s get a This Fool question out of the way immediately: Is there any chance we might get a third season on some other platform?

I don’t know. I truly wish I knew, dude. I feel more pessimistic about it every day. You know, if somebody showed interest—Netflix, Amazon, HBO—in the way it happened with [the show] The Other Two, which was canceled on Comedy Central then later showed up on HBO MAX; or Girls 5Eva, which was on Peacock, then Netflix…well, I hope there’s a chance that maybe somebody out there at those streamers loved the show and wants to have it there.

It would be nice to get some closure for the characters. Did you see the show going for a long time anyway? Maybe even with one more season, you could wrap it up, right?

The way we told our stories with every show, every season, there was a kind of finality, so I truly think that the kind of show I made with This Fool is not a show that goes 10 seasons. Maybe it’s four or five seasons.

I still don’t get it. I mean, y’all had The Sopranos’ Michael Imperioli. And it turns out he’s so funny!

Michael Imperioli was truly amazing. Getting to work with that guy as a fan of his, and that he was excited by the show? I mean, we sent him the script and he said ‘this is really funny and smart!’ He wanted to be a part of it, and he really gave it his all. Some of my favorite episodes are the ones that kind of center his character.

Your chemistry with Frankie Quiñones, who played your cousin, was really palpable on the show. Did you guys have a pre-existing relationship?

I used to go on the road with Frankie Quiñones. I’ve known him for 10 years now, and he was a really good friend before the show. Like, when he’d go out and headline on the road, he’d bring me out to open up for him. He’s a guy with whom I’ve always had a good rapport. We are like cousins in a sense—we know how to push each other’s buttons and we know how to laugh together.

How about some of the other side characters? It really seems like they’re people you truly know.

We found some of them from this amazing casting company called From the Streets 2 the Set; they specialize in people who fit a certain look, like former gang members who are interested in extra work, being actors, playing roles. That’s where an actor like Chris Calderon, who played the character Jorge, came from. He’s this amazing performer, and he was just in that Nathan Fielder show The Curse. That’s where we got Carlos Ayala, and he was this character who’d get nervous whenever we’d ask him a question; and he was so good, too.

Some of it was also people who come from standup comedy, like the guy who played Chef Percy. He’s a comedian we all know from LA named Jamar [Malachi] Neighbors. We always wanted to cast comedians from the LA scene, y’know, and he really made that character.

Esquire called you ‘the hardest working man in comedy’ last year What do you think that’s about? Is it hunger? Joy? Both? Neither?

I think a lot of it is that I come from a working class background. I was working at a warehouse. I mean, I was doing comedy, but working full-time while doing comedy on the weekends. When I sold and created This Fool with my friends Matt Ingebretson, Jake Weisman and Pat Bishop, I was working at a warehouse and I was literally driving a forklift and unloading trucks. I think a lot of that ‘hardest working’ stuff comes from my work ethic in comedy, too, because I treated standup like a real job, even though it was sometimes just open mics and the local scene. I was getting up every night, like three times a night, and just trying to work as much as possible. I feel like I’m still working hard, I’m still constantly trying to write new jokes, rewrite my current jokes, and I still get up at shows in LA to work on new material. If I can get up in LA seven or eight times a week, I consider that a win. I feel like I’m always kind of working hard towards that.

Can we talk about punk rock for a second? On This Fool, your character was constantly wearing shirts from punk bands. Are you drawn to comedy because its ethos is similar to punk’s—sticking it to the man and such?

I wore those shirts because I wanted to wear stuff I wear in real life. Julio is a version of me—he’s not completely who I am, but a version. I think it was natural and it didn’t feel try-hardy to wear those shirts.

As for if they’re alike…kind of. I think the only difference is that punk can take itself seriously, which is not a bad thing, because I’m not really into humorous punk bands. My favorites are bands like Fugazi, The Clash…I wouldn’t say Rage Against the Machine is punk, but they come from punk. And a lot of these bands take themselves a little more seriously, but I think the difference is that comedy is a little more irreverent, because it has to be by nature. What they do share is that you have to motivate yourself to do it. You have to do it for yourself. You have to make sure you get up every day and night and hustle and bustle. Comedy has that grind of punk. It has that work ethic.