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The Secret to ‘I Think You Should Leave’? Old Guys.

From Professor Yurabay to Detective Crashmore to that skunk Doug, the second season uses veteran character actors better than any other show on TV

Dan Evans

Soon after the second season of I Think You Should Leave With Tim Robinson premiered in early July, Bob McDuff Wilson got a phone call from his daughter. She’d just heard from her daughter, who’d caught Wilson’s appearance as a burger-snatching dinner guest on the Netflix sketch show. “She said, ‘Dad, your granddaughter called and said, “You know, granddad used the word ‘shit,’”’” Wilson says.

The family of the retired sixth-grade teacher/longtime actor was shocked. “I had never used profanity around my kids,” says Wilson, who’s 85 years old. “I said, ‘Well you better be glad they took the other stuff out.’ … I probably wouldn’t have been able to come home.”

In the opening sketch of the third episode, Wilson plays Professor Yurabay, a beloved business school mentor his former students have invited to a restaurant. Like most ITYSL sketches, things start remarkably normally before descending into utter chaos—in this case, the descent begins when the food comes and Yurabay eyes what’s on Tim Robinson’s character Dylan’s plate. Within moments, he’s gone from paying attention to the conversation to openly coveting what his protégé ordered. He eventually grabs the burger off the plate, mimes eating it, and puts it back—all while insisting, “I’m joking!” as the rest of the table looks on with increasing horror. And when Dylan finally asks whether he wants a bite, he takes it and never gives it back. “Dylan, I’m gonna eat the whole thing,” Yurabay declares. As his dinner companions watch in befuddled silence, he savors every single bite, looks to his left, looks to his right, then deliberately pops the last morsel into his mouth⁠—a highlight reel–worthy windmill dunk.

“That’s where my grandson said, ‘Well, that’s probably the way he eats, anyway,’” Wilson says.

After housing Dylan’s burger, Professor Yurabay veers into even stranger territory, threatening to blackmail his upset students. (This is the part when he says “shit.”) And in a final flourish, Wilson delivers a punch line that’s too dirty for him to even explain to his grandkids. For Wilson, who’s had dozens of small parts on television dramas and in commercials, it’s the kind of role that he’s been waiting decades to play. “I was born to do that,” says Wilson, whose wife Marion helped him record his audition at home. “I was voted the most comical in my high school yearbook.”

A lesser series might’ve made the octogenarian the butt of the joke, or ignored him altogether. But veteran character actors are I Think You Should Leave’s secret weapon. The show turns the spotlight on those whom Hollywood rarely allows to be under it. And finally served up a chance to wreak comedic havoc, they’ve grabbed hold of it and eaten it up like Dylan’s burger. Think Ruben Rabasa’s heavily memed focus group alpha dog, Biff Wiff’s cartoonishly ultraviolent version of Santa Claus, Richard Wharton’s sexually explicit Claire’s ear-piercing testimonial weirdo, and Wilson’s burger-obsessed mentor. These old guys are responsible for many of I Think You Should Leave’s biggest, most startling laughs. After all, no one suspects the grandpa in the fleece vest.

“You’re pulling actors from all directions of life,” casting director Leslie Woo says. “When the right actors can get that timing right and they understand the tone of it, that’s when the gold comes out.”

Bob McDuff Wilson in ‘I Think You Should Leave’
Screenshots via Netflix

While casting I Think You Should Leave, Woo considered getting the production’s rented Santa Monica office space soundproofed. She wanted the actors, particularly those still unfamiliar with the show’s hard-R-rated absurdism, to feel comfortable working blue without worrying about who might be listening. “For some of these roles,” Woo says, “you have to go all in.”

Take, for example, the lead of the sketch featuring a trailer for a straight-to-video-style fake action movie called Detective Crashmore, in which the title character is a bloodthirsty cop whose dialogue sounds like it was written by a 13-year-old boy weaned on bad ’90s cop flicks. His bon mots include: “Eat fuckin’ bullets you fuckers!” and “Oh, fuck, I like that gun.” And also: Crashmore is played by Santa Claus.

For that reason, Woo and the ITYSL team auditioned a lot of Santa types—and asked them all to curse. A lot. Woo remembers watching one grizzly bearded man who recorded his audition on the shoulder of a highway. “He was doing it on the side of the 5 on his way to Fresno,” Woo says. “Screaming into the tape, ‘F you, F this.’ And I see all these cars flying by behind him. ... I’m thinking, ‘I hope the guy gets to Fresno. I hope he gets there OK.’”

That mystery may never be solved—the role of Santa eventually went to another hirsute, foul-mouthed baby boomer instead: a man named Biff Wiff. If you watch a lot of TV, the 72-year-old actor may look familiar: He’s popped up on everything from 9-1-1 to Westworld to Brooklyn Nine-Nine to NCIS to iCarly to L.A. Law to Night Court to Moonlighting. Thanks to the prodigious beard he began growing 20 years ago, he’s spent the past decade and a half getting work as Santa Claus. “The real-bearded Santa Clauses have a whole fraternity, and they go on junkets together,” Wiff says. “So they’re a real clique. When you walk into a commercial audition there’s 15 guys there. And every single one, you look and say, ‘Yeah, that’s Santa!’”

Wiff admits that he didn’t quite understand the Santa-as-Crashmore joke until later, when he first watched his episode. “There were a lot of things that made me laugh and I didn’t know the laughs were there,” he says. “Because it was so violent!”

Yet Wiff still felt comfortable enough to go all in. Even if he didn’t get the bit at first, or understand why Santa was written as a surly, pretentious actor, he trusted the creators of ITYSL. They thought that he could be funny, and he wanted to reward their confidence. “We tried it several different ways,” Wiff says. “And it was a real lot of loosey-goosey going on. I really enjoyed it.”

Despite not appearing in the Crashmore sketch himself, Robinson took time to offer feedback. “I want to just brag on Tim a little bit,” Wiff says. “For the whole time I shot, he was there. Before I got there, he was there. And he was there after I left.”

Like a top pro wrestler, Robinson is skilled at putting his costars over. Even when he’s playing an off-the-wall character, he manages to boost his less-prominent sketch mates. Broadway veteran and prolific voice actor William Frederick Knight, who’s 87, was one such beneficiary. He’s Doug, the guy whom Robinson’s character Mike repeatedly refers to as “a fucking skunk!”after Doug calls him out for spending his per diem on ridiculously patterned shirts at a men’s store called Dan Flashes.

“I’ve played a lot of authority figures,” says Knight, who recalls improvising several of his lines. “I played General MacArthur and General Patton. So it plays really well as a straight man against Tim’s character.”

Knight started watching I Think You Should Leave only after landing an audition, but it didn’t take him long to figure out Robinson’s shtick. To him, it’s as distinct as Jack Benny’s or Rodney Dangerfield’s. “I kind of got his hook,” Knight says. “Every sketch is built on the fact that wherever he goes, he’s gonna stick out like a sore thumb. He’s gonna say the wrong thing. They always say never talk about ropes in a house where someone just hung themselves. … Tim’s gonna talk about ropes.”

Biff Wiff

Robinson is the star of I Think You Should Leave, but the show wouldn’t be nearly as funny without a supporting cast that’s as committed to every single bit as he is. In ITYSL, there are no throwaway roles. Even the actors with just a line or two⁠—like the waiters who warn Robinson and his boys against making “sloppy steaks”—are hilarious.

Last season, Woo says that there were about 10 roles named “man” or “old man.” But each was unique. One of those went to Rabasa. The now-83-year-old actor’s performance in the “Focus Group” sketch led fans to dress up as his character on Halloween, but he’d initially only read for another, single-line part. “I remember my wife and I just watching him audition over and over,” Woo says. “’cause we could not stop laughing.”

Robinson, ITYSL cocreator Zach Kanin, and the show’s producers loved Rabasa so much that they gave him a bigger role. “That really just felt like a golden egg that we came across,” Woo adds.

But though he’s now the most recognizable, Rabasa is far from the only treasure that ITYSL has unearthed. “There’s just been so many times where it’s hard to keep a straight face, especially when you’re in the room with the people,” Woo says. “It’s just such a pleasure. Especially now. We can take all the laughs we can get.”

Actors like Knight, Wiff, and Wilson have always had comic timing, but both the show’s writing and Robinson’s presence helped bring it out in unexpected ways. On set, Wilson was encouraged to improvise, which is how he arrived at his most memorable line: “Gimme that!”

“Even watching Season 2,” Woo says, “I could’ve never even guessed at how Tim would’ve played [opposite] those roles.”

That element of surprise has elevated I Think You Should Leave above other sketch shows. It turns unlikely troublemakers into chaos agents. And because you can rarely predict where—or who—exactly the laughs are going to come from, you can’t look away.

Now when these veteran character actors go to a shoot, they’re no longer “old man”—they’re “old man from I Think You Should Leave.” “It’s more than what I ever thought it would be,” Wiff says about the response to his performance. People on sets come up to him now and tell him how much they loved Crashmore. “It was really quite an experience.”

As someone who’s still being recognized for his two-episode run on Star Trek in the ’60s, Knight knows what it’s like to be part of a show with a cult following. And the ITYSL fans he’s spoken to are just as dedicated as Trek obsessives: “There are Trekkie types that are following this show. They know all the dialogue.”

Wilson, who retired from teaching in 1994, has heard from friends from as far away as France and Tanzania. “I didn’t know I had so many relatives,” he says. “It’s been exciting.” Strangers are even approaching him in public and saying “Gimme that!”

Like Professor Yurabay, Wilson remains in contact with many of his former students. “They still come by and take me to dinner,” he says. “Matter of fact, I was supposed to be going out to dinner with one tonight.”

It’s unclear whether Wilson was planning on ordering a burger.

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