FLASHBACK: 'The Ben Stiller Show' Turns 25! Why the Actor Laughed at Winning an Emmy for the Series

On Sept. 27, 1992, The Ben Stiller Show premiered on FOX, showcasing the titular star’s now well-known talent for emulating celebrities and crafting original characters. The sketch comedy series was abruptly canceled before its first season finished airing, but almost a year after it debuted, the show won an Emmy for Outstanding Writing in a Variety or Music Program. 

“We had no idea,” Stiller told ET backstage at the 45th Primetime Emmy Awards. Apparently, none of the show’s writers had attended the ceremony with the  notion they might beat out comedy institutions such as Saturday Night Live and Late Night with David Letterman. At some point leading up to the night, Stiller thought maybe he should put together a few words, just in case. “And then at the last minute, I thought, You know, I'm not gonna prepare a speech, because I'll feel like such a jerk when I don't win.”

Created by Stiller, Judd Apatow and Jeff Kahn, TBSS is considered by many critics to be a defining influence on modern sketch comedy. With featured players Andy Dick, Janeane Garofalo and 2017 Emmy nominee Bob Odenkirk (for Better Call Saul), the series defied conventional satire by producing sketches that parodied both pop culture and traditional joke structures. Its approach is perhaps best encapsulated in the take-off of 90210, “Melrose Heights: 9121024026,” in which the high school clique ridicules a peer for potentially being a robot.

Standing alongside Stiller in the Emmy press room were several recognizable names in comedy, including Apatow, Odenkirk, David Cross, and Dino Stamatopoulos. After producing the short-lived Freaks and Geeks and Undeclared, Apatow found success on TV a decade later with Girls, soon followed by Crashing and Love, which had TBSS writer Brent Forrester as a producer for its first two seasons. 

“Seriously, I gotta say there were people out there who liked the show. I run into them in the street every once in a while,” Stiller told the press room, adding: “For the people who liked the show, this is nice. It kind of translated.”

Popular sketches from the series included parodies of Die Hard,Cops, TheLast of the Mohicans, and Cape Fear. Having already displayed his Tom Cruise impression in a parody of The Color of Money on SNL, two more sketches on TBSS solidified Stiller’s connection to the star that would culminate with Cruise’s appearance in 2008’s Tropic Thunder

“We all know exactly how great it would have been,” said Cross in the press room postmortem. His HBO sketch series with Odenkirk, Mr. Show with Bob and David, became one of the most significant collaborations of any of the TBSS writers. The pair last appeared together in the 2015 Netflix series With Bob and David, and will share screen time with Tom Hanks next year in The Post, a Steven Spielberg-directed film about the Pentagon Papers

Stiller closed their press room remarks with: “I just want to say, all of these guys work so hard and I'm so proud of everybody here.” Of course, their Emmy win was just the beginning of the writers’ karmic retribution. One of the show’s legacies (aside from our collective desire to murder Doug Szathkey) is the numerous careers in TV and movies from TBSS veterans in the 25 years since. 

As the group exited, Cross grabbed the final word: “Watch for our cable access show on channel three.”

The Ben Stiller Show is now streaming on Amazon.