Chris Estrada loves wandering around San Francisco.

Standing on the corner of Columbus and Vallejo with a slicked-back gentlemen’s cut and a crisp, black T-shirt, the Los Angeles-born stand-up comedian is arguably one of today’s funniest entertainers. [pullquote size="medium" align="right" citation="Comedian Chris Estrada"]‘I truly love walking around San Francisco just because it’s such a beautiful city.’[/pullquote] He’s also the star and co-creator of the widely acclaimed TV series This Fool, now in its second season on Hulu. While actors and writers, including Estrada, continue to strike over labor disputes, the 39-year-old is making audiences laugh in person at some of the best comedy clubs in the country, including a current run at the Punch Line in San Francisco.

“I truly love walking around San Francisco just because it’s such a beautiful city,” said Estrada while visiting Molinari Delicatessen for a quick lunch on Thursday afternoon. “We’re right down the street from City Lights. I love City Lights. It’s one of my favorite bookstores in the country.”

He’s also a fan of Mr. Bings in North Beach and the quieter side of the Sunset because it’s right by the water (he loves the fog). Estrada’s no stranger to the Punch Line, where he’s previously been an opener, and he’s performed at Cobb’s and Comedy Central’s Clusterfest at the Civic Center.

This time, however, Estrada makes his headline debut at the venue where the likes of comedy figures such as the late Robin Williams, Dana Carvey and Dave Chappelle have all stood on stage making audiences laugh through the decades.

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This weekend, Estrada isn’t alone. He’s tapped local comedian Allison Hooker as host, and L.A.-based comic Zack Chapaloni to warm up the crowd.

Estrada’s comedy style is both personal and universal. He can write a joke with details that instantly resonate with Latinos, and still have the entire audience laughing. He wants everyone in on the joke.

He also draws on his own life: the absurdity of missing the thrill of toxic relationships, or how being nice is an “ugly people quality” while calling himself “an ugly fool with a heart of gold.”

Making audiences erupt in laughter at clubs like the Punch Line this past week is something Estrada said he’s been working toward for the last decade — and it feels good.

“That club is really special. It’s just beautiful in there. To me, it’s one of the perfect clubs in the country,” Estrada said. “It’s low ceilings. It’s incredibly intimate. It fits about 180, maybe 200 [people], which is nice. It’s just small, wide and that backdrop is iconic. That painted backdrop of San Francisco — I love it.”

‘I just kept going and going’

Losing a nighttime job as a valet for the Beverly Hilton changed the trajectory of Estrada’s life. Having grown up in working-class neighborhoods like Inglewood and South Central, he often jokes that he always held “three shitty jobs” that would pay him the equivalent of one shitty job.

When he lost the valet gig — parking luxury cars at star-studded events like the Golden Globes — his nights suddenly freed up. Estrada worked up the nerve to finally give his stand-up comedy dreams a chance.

A man in a blue jacket sits inside a bookstore with a full bookshelf behind him. — Comedian Chris Estrada hangs out at City Lights Bookstore in San Francisco’s North Beach neighborhood on Aug. 17, 2023, during a headlining run at the Punchline comedy club. (Beth LeBerge/KQED)

“I went and I had a decent set the first time. And then, I was like, ‘Fuck it. I don’t have anything to do at night anymore so I’m just going to keep doing this,’” he said. “I kept doing it blindly. I just kept going and going.”

He said headlining the Punch Line feels like a real stepping stone, especially when he reflects on the trips he used to make to San Francisco from Los Angeles just to watch performances and get a feel for the local scene.

“The clubs out here, the people out here, they’re pretty savvy, comedically,” he said. “Audiences, they’re just a sharp, city audience.”

Getting inspiration from Bay Area punk

Besides his affinity for stand-up, Estrada is also a huge music enthusiast. He admits to driving out of his way to places like Going Underground Records in downtown Bakersfield just to pick up a rare album. He loves Joe Strummer, and often wears punk and hardcore T-shirts from local and national bands. So it’s no surprise to learn that Estrada is well-versed in Bay Area punk bands and long-lost music venues in San Francisco. [pullquote size="medium" align="right" citation="Comedian Chris Estrada"]‘San Francisco itself has such a history of punk music. I also love Dead Kennedys. I love Spazz, an old powerviolence band. There are so many Bay Area punk bands that I love.’[/pullquote] “I also like to walk around and look for old punk venues that don’t exist anymore. There was this Filipino place out here in the ’70s called Mabuhay Gardens and they used to rent out its place to punk shows,” he said. “There was another place not too far from here called the Deaf Club. It was a club for deaf people and then a lot of punk bands used to perform there. I always look around for these places.”

He’s a fan of Berkeley-formed hardcore punk band Spitboy, and said drummer Michelle Cruz Gonzales attended one of his Punch Line shows this week. He enjoys The Avengers, The Dils and Crime. He also recommends new bands like Oakland punks Deseos Primitivos, who he found on Bandcamp and whose album he immediately bought at a record store in downtown L.A.

“San Francisco itself has such a history of punk music,” he said. “I also love Dead Kennedys. I love Spazz, an old powerviolence band. There are so many Bay Area punk bands that I love.”

Music accompanies Estrada on the road, bringing him comfort on long drives and flights while on tour. It’s also what gets him in the right mindset before he takes the stage. [aside label='More on Bay Area Music' tag='bay-area-punk'] “There’s a song, it’s not like an energetic song, it’s called ‘State of the Art’ by Jesse Malin. Then, there’s another song called ‘Ante Up’ by a hip-hop group called M.O.P. — and that just has such a strong energy,” he said. “‘Ante Up,’ because it’s such an amped-up, hyped song, it’s about robbing rappers, it just gets me in a really good mood when I need it. But when I feel anxiety, the other one calms me down.”

With his last remaining performances at the Punch Line, Estrada hopes to win over people in the crowd who aren’t as familiar with his stand-up career. He recognizes that Hollywood fame only lasts a few seasons for many in the industry. It’s comedy he’s betting on — and he aims to leave audiences across the country wanting an encore.

“Because of This Fool, most people are coming to see me because of that. Some of them don’t know me as a stand-up comedian. I don’t know how long I’ll have the show. Maybe we’ll have a third season, maybe we won’t. Who knows? At some point, it ends,” Estrada said.

“I don’t want [audiences] to keep coming because they know the show,” he added. “I want a large part of them to keep coming because they know me as a comedian.”

Chris Estrada performs at the Punch Line in San Francisco through Aug. 19. Details here.

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