When we think about Ben Stiller's early career, we tend to think of The Ben Stiller Show and Reality Bites, two acclaimed works that came before he fully broke into the mainstream. The next 25 years of his career — from There’s Something About Mary to the Fockers, the Tenenbaums, and the Night(s) at the Museum — are seared into the collective unconscious of anyone breathing over the same span. But aside from a few cameo appearances, Ben Stiller has laid low since he directed Escape at Dannemora four years ago. That drought ends this week when Severance, a limited series thriller for which Stiller directed six of nine episodes, premieres on Apple TV+. Looking back at his career, few corners of it could qualify as being under-explored… except for one. In celebration of Stiller's return to TV, let's revisit his brief stint as a cast member on Saturday Night Live.
Before Stiller had his own sketch show, he joined the Not Ready for Prime Time Players as a featured player in the back half of the show's 14th season in the spring of 1989. The cast at the time included Dana Carvey, Jon Lovitz, Jan Hooks, and Phil Hartman. Mike Myers was another freshman. Opportunity was there for the taking, and Stiller already had a track record of success getting airtime on the show. Two years earlier, he'd self-produced and starred in a parody of the Tom Cruise/Paul Newman pool-shark movie The Color of Money; Lorne Michaels liked it and put it on the show. Some people grasp for airtime like that their whole careers and never make it. Which made what happened next somewhat surprising.
Stiller was asked to join the cast as a featured player, but only lasted four episodes. His time on Saturday Night Live was so brief it only warranted a throwaway mention in Live From New York, the exhaustive oral history of the show by James Andrew Miller and Tom Shales. Said mention was as part of a longer story about Stiller bailing on a scheduled hosting gig in the wake of the September 11 attacks. (That’s on page 535 of the paperback, if you’re interested in learning more about that.)
Looking back, a number of the things that initially made Stiller famous were present during his short time on the show. Admittedly, most of Stiller’s appearances were small parts, and so the few sketches Stiller appeared in are difficult to find unless you have a subscription to Peacock, where all four episodes from March 25 to April 22 1989 are available for streaming. One sketch, called “Celebrity Restaurant” (below) lives on on Youtube because, for a brief second, you can see Stiller, Conan O’Brien, Dana Carvey, and Bob Odenkirk in the same frame, a kind of tasteful stoner's Mount Rushmore of '90s comedy. Stiller’s character appears to be arrogant and dismissive, a real jackass in a suit — a role he’d reprise five years later, in Reality Bites.
Stiller also briefly shared the screen with another comedy legend, Mary Tyler Moore. In a sketch called “Customs,” she plays an a customs agent whose disarming demeanor makes everyone she meets admit what they’re smuggling into the country. Phil Hartman didn’t want to pay the duty on a bracelet for his wife, Kevin Nealon is a spy, and Dana Carvey admits to smuggling a ton of cocaine. Stiller’s crime is minor by comparison — he cut the line — and doesn’t require any real banter with Moore. They would end up reuniting a seven years later, in David O’Russell’s Flirting With Disaster, in which Moore played Stiller's mom.
Stiller also appeared in the very first Sprockets sketch, which would become a huge recurring hit for Mike Myers. Both men ended up certified movie stars eventually, and were, beyond the show, effectively A-list comedy peers. But only Myers was backed by Broadway Video. He’s still working out the Sprockets formula here — Dieter does not shout anything, in fact it’s all very reserved compared to what the character would become. The same goes for Stiller. He debuted his Eddie Munster impression in this sketch, then took it with him to The Ben Stiller Show, where it became a recurring bit. It’s like a Comedy Extended Universe crossover sketch, but at the time, neither guy nor character were famous. This sketch existed on the internet at one point, but for now we'll have to settle for this 45-minute supercut someone made of Eddie Munster’s appearances on The Ben Stiller Show.
Stiller’s most lasting contribution to SNL was probably what initially got him on the show: his Tom Cruise impression. Once he joined the cast, it only took two episodes before he broke it out again, this time playing Cruise’s character from Rain Man (above). It can be strange to see a younger Stiller playing someone this intense and unlikeable. His Cruise impression is closer to White Goodman, the villain from Dodgeball, than it is to Greg Focker or Ted from There’s Something About Mary. Of course, Stiller would take that impression with him, too — all the way to a famous sketch with Cruise himself for the 2000 MTV Movie Awards.
It was Stiller’s desire to direct that led to his brief SNL gig. When he joined, he wanted to make short films like Albert Brooks did at the very beginning of Saturday Night Live. It’s what got him on the show in the first place, after all. Once he realized he’d just be a sketch performer, he split.
It’s fun to think about what might have been if Stiller stayed — Sandler, Rock, Farley, Meadows, Schneider, and Spade joined the show only a few years later. Would he have thrived and become famous alongside them, or fall into the background? Would we lose his friendship with Owen Wilson? What if Ben Stiller played opposite Farley in Tommy Boy instead of Spade? We’ll never know, but clearly it worked out well for everyone involved.
Connor Simpson writes occasionally, but bartends more often. He knows how curling works and loves a chilled red. You can follow him on Twitter @connorsimpson.