You probably remember Ben Stiller as the guy who played Michael Cohen or the fashion icon Derek Zoolander popping up on Weekend Update. But most people totally forget he was actually a full-blown cast member back in 1989. It didn't last. He lasted exactly four episodes before he basically just walked out. Honestly, it’s one of the weirdest "what ifs" in comedy history. If he had stayed, we might never have gotten The Ben Stiller Show or the "Frat Pack" era of the early 2000s.
The Ben Stiller SNL Skit That Started It All
Before he was even hired, Stiller made a huge splash with a pre-taped film. In 1987, the show aired a short he produced called The Hustler of Money. It was a pitch-perfect parody of the Martin Scorsese film The Color of Money. Stiller played a send-up of Tom Cruise’s character, while John Mahoney took on the Paul Newman role. Instead of pool sharks, they were bowling hustlers.
Lorne Michaels loved it.
The bit worked because Stiller’s Tom Cruise impression was—and still is—uncanny. He doesn't just do the voice; he captures that specific, high-intensity squint and the manic energy. This success is what eventually led to him being offered a spot as a writer and featured performer in Season 14.
Why he quit so fast
He joined the cast on March 25, 1989. By April 22, he was gone. That is a blink-and-you-miss-it tenure. Stiller has been pretty open about why it didn't work. Basically, he wanted to make short films like Albert Brooks had done in the early days of the show. He wasn't interested in the "Live" part of Saturday Night Live.
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The grind of the show is legendary, but Stiller realized early on that his heart was in directing and pre-taped segments. When the producers told him they wanted him to focus on the live sketches instead of his filmed pieces, he just didn't see the point in staying. He followed his gut, which is a pretty ballsy move for a young comedian in 1989. He left for MTV, and the rest is history.
The Most Iconic Ben Stiller SNL Skit Moments
Even though his time as a cast member was short, Stiller returned to host and make cameos multiple times. This is where the real "greatest hits" come from.
1. V-Necks (The Digital Short)
When Stiller returned to host in 2011, he teamed up with Andy Samberg for a Digital Short that felt like a spiritual successor to his early 1980s work. It starts with a simple premise: two guys wearing V-neck shirts. But then, they keep getting deeper. And deeper. By the end, the V-necks are practically down to their ankles.
It was a meta moment. Stiller actually told Samberg that the way The Lonely Island guys were making Digital Shorts was exactly what he wanted to do back in 1989, but the technology and the "vibe" of the show just weren't there yet.
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2. Bruce Springsteen: Just the Stories
Another standout is his Bruce Springsteen impression. On his own show, he did "Counting with Bruce," but on SNL, he took it further with a fake commercial for a 5-disc DVD collection called Just the Stories.
The joke is that Springsteen's fans love his rambling, earnest stage banter more than the actual music. Stiller-as-Bruce sits on a stool, denim shirt unbuttoned, telling endless, meandering stories about his father and the Jersey Shore. No music. Just "The Boss" talking for twelve hours. It’s a surgical strike on Springsteen’s persona.
3. Derek Zoolander on Weekend Update
You can't talk about a Ben Stiller SNL skit without mentioning Zoolander. While the character eventually became a movie franchise, his appearances alongside Bill Hader’s Stefon are comedy gold. Seeing the world’s most famous male model try to interact with a New York City club correspondent is as chaotic as you’d expect.
4. The Michael Cohen Cameos
In more recent years, Stiller became the go-to guy for Michael Cohen during the Trump administration's various legal sagas. He brought a certain "panicked puppy" energy to the role that resonated with audiences during a very weird political era.
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What We Get Wrong About His Tenure
People often think Stiller was fired or that he failed on the show. In reality, it was the opposite. He was "too big" for the format they wanted him to fit into. If you look at the 1989 cast—Dana Carvey, Mike Myers, Phil Hartman—it was a powerhouse of live performers. Stiller was a filmmaker who happened to be funny.
There's a great sketch from his brief stint called "Celebrity Restaurant" where you can see him, Conan O’Brien, Bob Odenkirk, and Dana Carvey all in the same frame. It’s like a time capsule of the people who would define comedy for the next thirty years.
How to Find These Sketches Today
If you’re looking to watch a specific Ben Stiller SNL skit, your best bet is Peacock, which has the full episodes from Season 14. YouTube is great for the "Best of" clips, especially the Bruce Springsteen bits and the V-Necks short.
Next Steps for SNL Fans:
- Watch the 1987 short "The Hustler of Money" to see the exact moment Stiller caught Lorne Michaels' eye.
- Compare his SNL Bruce Springsteen to his Ben Stiller Show version to see how his parody style evolved over 20 years.
- Check out the 2011 "V-Necks" Digital Short to see the bridge between the 80s "short film" era and the modern viral video era.
Most fans only see the movie star, but digging into the specific Ben Stiller SNL skit history shows a guy who knew exactly what he wanted to do, even if it meant walking away from the biggest stage in comedy.