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I did a joke that came across in a way that made it seem like I was not sympathetic to the cause, as if I were almost pro-cop. The line between race and humor is a very tricky one to walk.

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Then, when I saw Dick Gregory, I said, “Oh! All that stuff I’m really riled up about and find interesting that I never talk about on stage? I want to talk about that stuff too.’” It was a constant battle to stay young, and that’s not where my passions live. I was getting into my mid-thirties and a switch flipped. I was forcing myself to watch MTV 2 just to keep up on trends-you’re making a Soulja Boy joke when you’re dealing with a crowd that grew up on Tyler the Creator. Then it was drinking, then it was relationship stuff, sports. And it was hard to tell when you were watching stand-up versus when you were watching a speech versus watching a one-person show. Most of my early stand-up was just college kid gripes. And I got to watch him for 90 minutes meticulously talk about civil rights and then bring humor into it. The first year of the Wild West Comedy Festival in Nashville, I got to open for Dick Gregory at Zanies. You were changed by seeing Dick Gregory in 2015. Comedy changes people and people change the world. So to get up there at the correspondents dinner and think that I'm going to finger wag everybody into finally agreeing to let go of CRT-comedy doesn't change the world. You could, but it goes back to when I was the fourth chair on a morning radio show: What has everybody already said before I open my mouth? I am trying to challenge myself to say anything about George Santos other than, ‘He's a liar.’ You can't shame people into behaving correctly. President Barack Obama, in 2011, ridiculed Donald Trump, who was in the audience, and maybe goaded Trump into running for president.

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Stephen Colbert, in 2006, did a brilliant, controversial Colbert Report style routine where he filleted President George W. Vanity Fair: This event has a daunting history. “Introducing myself to the world while at the same time holding Democrats accountable for what they have and haven’t done, while at the same time getting Republicans to maybe just admit that they don’t believe all the bullshit they spew.” Wood recently spoke with Vanity Fair about how he will try to pull off all that, while at the same time getting laughs, with about 20 minutes of material. “I haven’t been this intimidated by a gig since Showtime at the Apollo in 2001,” he says. On April 29, though, Wood will appear for the first time in front of one of the strangest rooms any comic can be invited to play: The annual White House Correspondents’ Dinner, where the audience of 2,500 is made up of Washington’s media and political elite, with President Joe Biden sitting on the dais a few feet away, as Wood delivers his jokes. One benefit of all that work is that Wood has encountered nearly every possible comedy challenge-from performing in front of hostile club crowds to headlining his own hourlong Comedy Central specials, from being fired from a morning radio gig to a stellar nearly eight-year run as a correspondent on The Daily Show. In the 25 years since, the longest he’s ever gone without performing in public is 11 days. started doing stand-up when he was 19 years old.







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