News & Politics

That Time Neal Katyal Took an Improv Rap Class So He Could Be Like Lin-Manuel Miranda

“It made Supreme Court arguments look like nothing”

Photograph courtesy of Neal Katyal

“I’ve been friends with Lin for a long time. His lyrics and writing are just, I think, Shakespearean. And this other thing he does—perform freestyle improv rap with the group Freestyle Love Supreme—has blown me away since the moment I saw it. I basically thought: What is the thing I’d be worst at in my life? And it would be that, because I can’t really sing, I’m not particularly funny, and most importantly, all my speaking, like my oral arguments, is so planned. The words are the opposite of spontaneous.

“But when Freestyle Love Supreme launched an academy, I decided to apply. I went up for my first class in New York on a Tuesday in September. I was more nervous for this than virtually anything. It made Supreme Court arguments look like nothing. There were 18 of us. A bunch were real pros. My whole goal was not to be the worst.

“Actually, the first class was not as traumatic as I’d feared, in part because we didn’t have to sing freestyle right away. Instead, they’d throw us a word and we had to tell a story. My word was ‘plant.’ At first, I was like, God, what am I going to say? Then I realized I had this story, which had just happened to me, about my mom. When I was growing up, she’d bought spider plants. When they overgrow, you have to keep cutting them and creating new ones. They were now all over her house, and she’d just decided it was too much, and she gave them all away. I talked about my conflicting emotions about her getting older. I realized, wow, all that came from one word.

“By the third and fourth classes, it was really about rhyme and music, and those were hard for me. I felt quite uncomfortable singing, and the rhyming just did not come naturally. But the thing I took away is that you all have to support each other. Everyone’s going to flub. The whole idea is you riff off each other, and when somebody drops the ball, you cover for them. That was super-interesting to me, just as a life skill.”

—As told to Marisa M. Kashino

Senior Editor

Marisa M. Kashino joined Washingtonian in 2009 and was a senior editor until 2022.