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Comedian Hari Kondabolu will perform Nov. 1-3 at Rooster T. Feathers in Sunnyvale. Courtesy Ali Imam.

From the personal experience of becoming a father during a global health crisis to the extremely problematic politics of the White Replacement Theory, Hari Kondabolu’s latest streaming special “Vacation Baby” covers a broad spectrum. He will bring his signature humor — in a whole new set, no less — to the Sunnyvale stage this weekend.

He will perform at Rooster T. Feathers on Nov. 1-3. 

“If a special has come out, I try not to repeat much of anything from the previous special because I feel like if I’ve already gone on tour and people have already seen that special they should get a new hour,” said the 42-year-old stand-up comic in an interview with this publication.

For Kondabolu, writing fresh material is something that takes place on the fly, because in his line of work, pretty much everything in life is grist for the mill, including everyday interactions, observations, travels and conversations with people. “Everything is there; it’s not like I’m scouring sites looking for things to write,” he said. “Sometimes I do, when I’m on a podcast that’s news-related or when I’m on NPR and I have to write jokes for a show.”

Kondabolu often goes through his old notebooks for material and writes jokes based on observations he made in the past, as far back as his teenage years, even. “I’ve been doing this since I was 17 years old, that’s over 25 years of writing things down alone; I keep all my notebooks, I don’t lose anything, and every now and then I’ll just pull out random books and start flipping through old pages and the old thoughts will spur new thoughts,” he said about his process. Sometimes, thoughts he might have jotted down years, even decades, ago might make sense to him today, now that he’s old enough to grasp their meaning. “Even stuff I wrote when I was 19 or 20 … I wasn’t ready to write the joke then but the observation is still strong and I can look at it and feel I’m old enough to understand what this fully means.”

Speaking of observations he made in the past, around eight years ago Kondabolu created a documentary titled “The Problem with Apu,” which took the example of Apu Nahasapeemapetilon, an Indian character from “The Simpsons,” to challenge the narrow way in which South Asians were represented in popular culture at the time. 

Hari Kondabolu says his comedy style has evolved to be more personal, talking about his family life and relationships, but he still takes on big-picture topics as well. Courtesy Will Devito.

While the film definitely helped increase his popularity, one of the “frustrating” outcomes was that his work was perceived as being centered only on themes the documentary dealt with, like identity and racial representation. “But it was never the bulk of my stand-up material, it was never the bulk of who I was,” he said. Of course, he still draws on issues like race in his comedy, across topics. “Talking about race, though, isn’t the same as talking about racial representation.”

Besides, his brand of comedy has evolved since. “It’s more personal,” he said. The context for a lot of his material is now rooted in personal anecdotes and his worldview is now filtered through different aspects of his own life, before it’s served up to the audience. It’s a kind of vulnerability that he believes leads to better comedy. “I always talked about things I cared about and that were personal to me in terms of my points of view on the world and I think people understood me through my values and what I represented but now I’m talking about my family, I’m talking about my kid, I’m talking about about relationships — it’s just a fuller version of me, which is something I’ve strived to get to. I think it’s best to be the most well-rounded person you can on stage.”

Once the audience gets to know and like a stand-up comic they’re that much more likely to receive the heavier, more political, material that person might bring to the stage, he finds. So his family, his friends and his travel stories come up a lot more in his scripts now.

“It’s like if you’re talking to a friend and you’re challenging them, your friend is more likely to be willing to be challenged because they know you, they connect with you, they have things in common with you, as opposed to a stranger ranting at you,” Kondabolu said, admitting it’s a recent discovery. “I think I’ve done a really good job of mixing some of the more aggressive material with personal stories and things that aren’t overtly ‘political.'”

Of course, when he says “political” he means it more as shorthand for the kind of controversial sociological and history-related subjects he draws on — like colonialism, geo-politics, power dynamics in the nation, consent, race and oppression — than hardcore political satire. One is more likely to come across the prison-industrial complex in his work than a deconstruction of Democrats and Republicans.

“It’s like if you’re talking to a friend and you’re challenging them, your friend is more likely to be willing to be challenged because they know you, they connect with you,” Kondabolu said of his act including more personal material. Courtesy Jennifer Giralo.

For him, the proverbial litmus test for topics he can and cannot play with is fairly simple. “It’s about gauging how comfortable and confident I am saying it on stage,” he said. “Is it worth the impact it has on the crowd?”

At the end of the day, it all comes down to the big questions — “Why are things this way? Why are things unfair? Why are we not viewing each other as full human beings?”

Among comedians who’ve inspired him are Stewart Lee, Margaret Cho, Chris Rock, Marc Maron, George Carlin and Richard Pryor, among others. 

Of late, Kondabolu has been painting to unwind, a hobby he discovered thanks to his little son. “When your career is other people judging you and laughing or not laughing … having something creative that is completely separate from all that is the healthiest thing I could do,” he said.

Hari Kondabolu performs Nov. 1-2, 7 and 9:30 p.m. and Nov. 3, 7 p.m. at Rooster T. Feathers, 157 W. El Camino Real, Sunnyvale. Tickets are $25-$35. roostertfeathers.com.

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