Smigel discussed the genius of ‘Stand-Up and Win’ during a recent talk with Neal Brennan

What’s the deal with observational humor? I know! It’s not observant, and it’s not humor!

Ever since Seinfeld took over the TV comedy industry in the early 1990s, every second-rate stand-up has kept a bad Jerry-Seinfeld-style set in their back pocket that barely gets a swift exhale when they test it out on an audience. While Seinfeld and Larry David made massive fortunes finding the funny in everyday circumstances, the popularization of Seinfeld’s sense of humor led to an epidemic of tedious, trivial comedy trotted out as if it was somehow hip and idiosyncratic for a comic to base their entire routine around whichever national TV commercials were making the rounds that week.

Legendary TV writer and former Saturday Night Live staffer Robert Smigel took note of this tired trend, and when Seinfeld himself hosted the show on April 18, 1992, Smigel had Seinfeld do a Seinfeld impression that proved to be the highlight of both of their contributions to SNL. Smigel discussed the famous “Stand-Up and Win” sketch during his recent appearance on Neal Brennan’s Blocks podcast, calling it “one of my favorite sketches that I ever did.”

“I loved him so much for having a sense of humor (about it),” Smigel said of Seinfeld’s reaction to his pitch for a scene featuring Seinfeld wannabes competing in a Jeopardy!-style trivia show where all the questions are rhetorical and all the answers are hack observational jokes. “It’s shitting on a certain type of comedy, and it’s not making fun of Jerry; it’s making fun of everything that was spawned from Jerry.”

Smigel noted that this wasn’t the first time he had satirized Seinfeld-style humor on SNL, remembering how, when Tom Hanks hosted the show in 1988, Smigel put him in a sketch called “The Stand-Ups” that had, essentially, the same premise as “Stand-Up and Win,” minus the game-show element. “Then Jerry came on the show, and I just thought, ‘So much of stand-up is just like people being rhetorical.’ And it started with Jerry, with the whole, ‘What’s the deal?’” Smigel recalled. 

Besides introducing “What’s the deal with airplane food?” to the lexicon of every amateur comedy critic in the world, Smigel says that his favorite part of “Stand-Up and Win” was when the contestants in the scene called on the category of “7-11 Employees,” the trivia question was simply an exasperated, “Who are these people?”

For Seinfeld’s part in what was essentially a self-parody, Smigel was extremely complimentary of the SNL host. “He was all over the idea,” Smigel explained. “He completely understood it. I mean, that guy’s brilliant.” 

Smigel even said that Seinfeld was “the only sitcom I ever thought that I could write for” — though, when David offered him a job on the Seinfeld staff, Smigel wasn’t able to accept, as he had to take care of his sick father at the time.

A couple years later, Smigel was the first head writer of Late Night with Conan O’Brien, and the possibility of him ever joining the Seinfeld writers’ room was kaput. But, I mean, what’s the deal with Late Night? Who are the ad wizards who came up with this one?