Second City alum, hired by Jimmy Fallon, is working for a different kind of ‘Tonight Show’

New head writer Rebecca Drysdale considers it ‘a fun challenge’ to see what kinds of comedy the team can generate as the star hosts from his home.

SHARE Second City alum, hired by Jimmy Fallon, is working for a different kind of ‘Tonight Show’

Rebecca Drysdale has been working as the “Tonight Show” head writer since April, communicating with her colleagues over email and Zoom.

Sunshine Sachs

Second City alum Rebecca Drysdale now is helping shape “The Tonight Show,” as illustrious a TV franchise as there ever was. And she’s doing it in her jammies.

As the head writer since April, she came aboard just after social distancing rules drove host Jimmy Fallon out of 30 Rock in New York. Now he’s fronting the show from his home, which is by no means a TV studio but does have some phones, his wife and adorable children, and an indoor slide.

Drysdale plunged into the work and, from her home in Los Angeles, is working with “Tonight Show” writers and producers mostly on Zoom. “I’m meeting all these people from the shoulders up,” she said.

For many TV veterans, the transition into quarantine production, with guests patching in from their kitchens and crew members contributing from several miles or several states away, has been wrenching. But Drysdale has found it sort of thrilling.

“I come from Chicago, where I was doing shows with two chairs and one light,” she said. “So I don’t feel limited. I feel like it’s a fun opportunity to figure out, ‘What can we do with these limitations? What can we do that we couldn’t even do live?’ I think that’s a fun challenge.”


Jimmy Fallon has been hosting “The Tonight Show” from his home.


An Ohio native, Drysdale fell into comedy while in college and moved to Chicago with a classmate, Jordan Peele, the future “Get Out” and “Us” writer-director. They put on two acclaimed sketch shows as the duo Two White Guys, and Drysdale co-wrote and performed at Second City e.t.c. in the early 2000s.

She collaborated with her old friend as a “Key & Peele” writer and also worked on “Baskets,” “High Maintenance” and the revival of “All That” before landing at Fallon’s show.

“It’s a huge, huge machine that’s certainly bigger than any machine I’ve ever worked for, and so a lot of it has just been, how do all these parts move and fit together, and what’s the best way for me to do what I do within that machine?”

Every ambitious idea requires plenty of scramble to make it happen, especially as quarantine spreads everyone apart. One heavy lift was a sketch last month imagining how “Tiger King” subject Joe Exotic will be played by Nicolas Cage in an upcoming TV series. In addition to getting costumes and makeup to Fallon, who would play Cage, the scattered team was building graphics, writing a song and emailing about how Fallon would record and lip-sync it.

Once it was complete, “I said to everyone, ‘That’s like a NASA launch.’ With everybody high-fiving and cheering at the end, just cause we pulled it off,” Drysdale said. “I felt like Ed Harris at the end of the many NASA movies he’s in.”

But shooting for the moon isn’t the only approach. One ongoing bit stars Will Ferrell, Kristen Wiig and other funny folks in a Zoom soap opera, “and we just really leaned into how crappy it was,” Drysdale said. “We did one episode where were using Zoom backgrounds to show they were in different parts of the world, and it looks terrible and we know that and we love it.”

Though she’s known many people in late-night TV comedy — notably her brother Eric Drysdale, a former writer for “The Daily Show With Jon Stewart” and “The Colbert Report” — this is her own first stint in that highly visible universe. It started looking to her like an enjoyable and even valuable place to work as the coronavirus turned America upside-down.

“When the quarantine started, Jimmy was right there doing shows from his house, and I felt like what he was doing was really positive and provided some much-needed levity,” Drysdale said. “And in the last couple years that’s something I’ve been really drawn to, more than, like, ‘Let’s take the piss out of everything and give everything an edge and undercut everything.’ ”

Still, she was surprised to be recruited from her “kind of prestige-y, little intimate” cable TV projects into the network juggernaut that is “The Tonight Show.”

“It was something that was not in my world,” she said. “And it still isn’t, because I’m in my pajamas at home.”

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