In the past few years, the comedian Nikki Glaser has breathed new life into the well-worn comedic form of the roast. Last year, she performed a roast of the football legend Tom Brady for a Netflix special, to much acclaim—with Conan O’Brien opining that “no one is going to do a better roast set than that.” Glaser has been on a hot streak since then, hosting the Golden Globes in January and touring the country with a new show. But rising to the top of the comedy world, Glaser tells David Remnick, hasn’t settled her insecurities, or her impostor syndrome. “It just never goes away— that feeling of not being worthy, or being thought of as less than,” Glaser says. It’s why, as Remnick notes, she insists on leading her set with a joke right out of the gate. “Part of it is I just know that people think women aren’t as funny, so I have to prove it right away . . . and then, ‘Can we all just relax and you can trust me?’ ”

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Florida Governor Ron DeSantis has shown himself uniquely skilled at attracting attention beyond the borders of his home state.  Just this month, DeSantis blocked state funds for the Tampa Bay Rays stadium after players voiced support for gun control in the wake of the mass shooting in Uvalde, Texas.  He’s also continuing a fight to punish the Disney Corporation for criticizing Florida’s so-called Don’t Say Gay law.  An Ivy League-educated anti-élitist firebrand, he is willing to pick a fight with anyone—reporters, health officials, teachers, Mickey Mouse—to grab a headline. DeSantis “practically radiates ambition,” the staff writer Dexter Filkins tells David Remnick. “He sounds like Trump, except that he speaks in complete sentences. … He’s very good at staking out a position and pounding the table and saying, I’m not giving in to the liberals in the Northeast.” Yet despite having been anointed by Donald Trump in his primary election, DeSantis has refused to “kiss the ring,” and many see DeSantis as a possible opponent to Trump in a 2024 Republican primary.

Michael R. Jackson’s Tony and Pulitzer Prize-winning musical “A Strange Loop” features a Black queer writer named Usher, who works as an usher, struggling to write a musical about a Black queer writer. Jackson’s work tackles the terror of the blank page alongside the terrors of the dating scene, and it speaks in frank and heartbreaking terms about Usher’s attempt to navigate gay life among Black and white partners. Hilton Als talked with Jackson about how he found inspiration in his own experience seeking identity and community. “I started writing the original monologue—building a sort of life raft for myself—to understand myself,” Jackson said. “It wasn’t until I got to a place of understanding that in my life I was caught up in a loop of self-hatred, that I could see what Usher’s problem was, and therefore what the structure of the piece was that would lead him out of that and into a better place.”

“A Strange Loop” is playing now at the Lyceum Theatre, on Broadway.