How Do You Cast a Sketch Show Like ‘I Think You Should Leave’? Look Outside the Comedy World

Casting director Leslie Woo tells IndieWire about the last-minute audition pivot that helped find one of the season's breakout stars.
"I Think You Should Leave with Tim Robinson"

Working on Netflix’s singular sketch show “I Think You Should Leave with Tim Robinson,” casting director Leslie Woo has looked at actors for about 160 different roles. Season 2 of the series largely picks up where the first left off: banal corporate meetings that careen into chaos, off-kilter ads for fictional products and services, friendly misunderstandings that devolve into madness.

But putting this follow-up season together, particularly from the casting side, brought some significant changes. Notably, since the first season had already been released when the Season 2 engine was revving up, anyone reading for a part in these latest episodes had a decent idea of what they would be thrown into. That wasn’t necessarily the case the first time around.

“Season 1, I was probably reading 60 to 70 people a day. It would just be a little bit more time consuming having to explain what it was, what the format was, and the tone of it. It was trying to figure out how far I have to commit myself to this Bozo voice with 50 auditions before it permanently damages my vocal cords. In the best way,” Woo said. “Having to explain sketches like that or the horse sketch in Season 1, now everybody already knows what it is. I think they’re really excited to not only read for it, but to see another season, because I think we all need some laughs right now.”

Even with that knowledge of the show, there’s still the classic paradox of casting, the idea that in some cases what makes the difference is not as much in the performance as it is a characteristic that’s often hard to quantify. It’s not that these roles (or these performers) are generic, but they offer a little more flexibility in what a particular performer might bring to it.

“In Season 1, we had like six roles that were named Dave. In general, Tim and Zach [Kanin] really gravitate towards people who reflect our worlds. I pull a lot of the inspiration from people I’ve worked with in the corporate world before I moved into the entertainment industry. It’s the little nuances of the day that get blown out of proportion that become the comedy. I definitely try to send them a very wide diverse array of actors. Dave could be 500 different types of guys,” Woo said.

Of course, there were absolutely “I Think You Should Leave” Season 2 roles that required a specific look or presence. Maybe chief among them is nesting-doll role of a man playing Santa Claus playing vengeance-hungry law enforcement official Detective Crashmore in an action movie. The process that eventually led to Biff Wiff (who’s gone on to have a standout year with other parts in “Dave” and “Everything Everywhere All at Once”) was one that nearly stopped in March 2020 before it even had the chance to start.

“The first day that I was going to audition the Santa Clause role was the day before everything shut down. Knowing that we had a bunch of older gentlemen coming in the next day, we shut things down a day early,” Woo said. “So I was doing live self-tapes and Skypes with them simultaneously. The experience of that was so wonderful and amazing, just to be able to talk to these guys for a minute and get to know them, but that was definitely one of the roles that presented challenges from a logistical standpoint.”

Some individuals have become some of the memeworthiest additions to the fabric of “I Think You Should Leave,” but just as important are the groups. A collection of folks sitting around a boardroom table, a clique of friends at a house party, the Sloppy Steaks-eating Dangerous Nights crew? Maybe the trickiest part of casting the show is finding people who you know will work as a unit before ever getting them in the same room.

“A lot of times they don’t want to lock in the cast of the full sketch until they know who everyone’s going to be. So I think that they’re ultimately looking out for that at the finish line. For me, it’s just wanting to send them enough options of different people. I think you get a good sense, as you’re watching the tapes, where you feel like there are holes and where you’d like more options in a certain age category. Just having a wider range is helpful,” Woo said. “In terms of auditions, sometimes people don’t even have a reader. You try and cut the sides down until it’s just one or two people in the scene. But in terms of the chemistry, I think that that is something that Tim and Zack absolutely spend a lot of time discussing and reviewing when they have those final choices to see who all mixes us together.”

Even through a revamped casting period for other roles, knowing what the show looked and felt like became a helpful reference point. Even via Zooms and self-taped auditions, there was an understanding on all sides that many of these roles call for a specific energy that’s the polar opposite of the one the guy in the name of the show is bringing.

“I Think You Should Leave with Tim Robinson”Netflix

“All of the acting is quite grounded. It’s a lot of the situational stuff that’s super exaggerated. Everything’s self-tape right now, so we’re not able to give those notes in the room, but we do actually include a note to send in your tapes and play it more grounded,” Woo said. “That was actually one of the big discussions in the very beginning of wanting to look everywhere, not just in the comedy world. Ruben Rabasa himself, he had done primarily character roles in in dramas. It’s being able to see that there is that training and that skill level in an actor to take adjustments on set. Not only this show, but any show, you don’t know how you’re going to be directed on the day.”

Casting children in anything is tricky. The sometimes-indescribable nature of “I Think You Should Leave” could theoretically make that even more complicated. But that’s another example of the show and its potential ensemble being on the same page.

“Every parent of a child actor is aware of the content that’s out there. That’s their own decision, what they’re comfortable with, in language or subject matter. There’s sometimes a handful of kids that are like, ‘This is a little too much.’ But often, it’s the parents who are like, ‘Yes, absolutely. We love the show so much. My kid will definitely be reading for this,'” Woo said.

With dozens of new people to find every season, that volume holds a special kind of promise for anyone auditioning: You may not be right for one particular part, but there are decent odds that there’s another opportunity waiting just a few sketches over.

“The guys will see someone reading a role and they’ll say, ‘Let’s cast them as this person in this other sketch.’ I think that they’re able to see the similar sketches: the office sketches, or the shops, or the commercials. There are so many amazing ones,” Woo said. “It definitely happens more often than not, and that’s just kind of what happens on every project. But on this one, because there are so many roles, there’s more of the freedom to do that.”

“I Think You Should Leave with Tim Robinson” is available to stream on Netflix.

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