Dana Carvey in Too Funny To Fail (Photo: Hulu)

How does a sketch show featuring some of comedy’s most brilliant minds become “one of the most spectacular failures in all of television history”? How does a series starring one of the most popular comedians on the planet alienate his fan base so swiftly and decisively that his career never fully recovers? And finally, is there some inversely proportional relationship between complete fiasco and eventual cult worship? These are some of the questions posed by the amusing, appropriately niche Hulu documentary Too Funny To Fail, although the more direct one is this: How did The Dana Carvey Show—arguably the most daring, prescient, talent-stacked sketch comedy to ever hit American network television—become such a massive flop?

If you’re the kind of comedy nerd who’s already skipping to the comments to quibble with that last statement, chances are you’re familiar with The Dana Carvey Show, if only as legend—or cautionary tale. The short-lived 1996 series was conceived as a starring vehicle for Carvey after he finally outgrew Saturday Night Live, a departure that was considered so momentous at the time, it found Carvey pondering his next move on the cover of Rolling Stone. He definitely had options. The manic impressionist fielded movie offers and was even courted for David Letterman’s Late Night desk before he decided he really wanted to bring sketch comedy—and a “counterculture” sensibility—back to the blandly smooth world of network primetime. ABC snapped him up, envisioning a sort of Carol Burnett-esque variety show with Carvey doing Garth and The Church Lady in between topical impressions. Carvey, fatally, had bigger ideas.

Instead, he recruited his old SNL collaborator Robert Smigel and Late Night writer Louis CK to help him create an absurdist, absurdly silly series in the vein of Monty Python’s Flying Circus. They then brought in a podcast-murderers’ row of comedy minds to write it, including then-unknowns like Charlie Kaufman (Being John Malkovich), Jon Glaser (Delocated), Robert Carlock (30 Rock), and Dino Stamatopoulos (Community). Finally, they hired an ensemble of raw improv talent like Heather Morgan and Bill Chott, along with a couple of young Second City guys named Steve Carell and Stephen Colbert. Together, they all set out to make something brilliant and bizarre, the kind of comedy that would offer a defiant up-yours to staid, formulaic sitcoms. ABC scheduled it right after Home Improvement.

“We had hired badass nerd pirates to blow up television,” Carvey says early on in Josh Greenbaum’s film, a knowing smirk permanently affixed to his lips. “This show would represent anarchy. This was blowing up the system.” Of course, The Dana Carvey Show didn’t so much blow things up as implode on impact. Viewers bailed by the millions during its very first sketch, a silly grotesquerie about Bill Clinton, outfitted with prosthetic, milk-spurting breasts that he used to nurse puppies and kittens. Critics savaged it. Sponsors abandoned and publicly denounced it. The staff received stacks of hate mail addressed, “Dear Human Scum.” And after a tumultuous, low-rated run of about a month, The Dana Carvey Show ended after just seven episodes, dealt one final indignity of having its finale yanked in favor of a very special Coach. It would be years—long after its ensemble went on to become some of comedy’s most influential voices—that anyone would give it a second look.

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For those who haven’t seen The Dana Carvey Show—well, first of all, just go watch it. The whole thing’s available on Hulu, or you can just YouTube all-time great sketches like “Skinheads From Maine” and “Waiters Who Are Nauseated By Food.” You’ll even see the very first edition of The Ambiguously Gay Duo, whose origins Too Funny To Fail explores in exhaustive detail. Go on. We can wait.

To those who still obstinately refuse to see it, or who think its reputation has been slightly inflated, there’s superficially little reason to recommend Too Funny To Fail. It’s a film for believers, made with affection and with the assertion that the show was truly underappreciated in its time. That said, even for those skeptics, there are a few pleasures to be found just in seeing all these future superstars in their young, hungry days. For Carell especially, lately tamped down in so many milquetoast dramedy roles, it offers a welcome reminder of just how explosively funny he can be, whether it’s in vintage Second City footage or Dana Carvey Show sketches like “Germans Who Say Nice Things,” where he and Carvey would shout greeting-card platitudes in a scary Teutonic accent.

It’s likewise fascinating to see Colbert, whose persona is entirely steeped in swaggering overconfidence, in a period of such vulnerable desperation that he used his baby daughter to beg for a job in his audition tape, or recalling how he stayed up for hours trying to perfect impressions of George Harrison and Oliver Stone. Greenbaum’s film offers genuine insight into Colbert’s obsessive work ethic, as well as his friendly friction with Carell, and it functions almost as a documentary within a documentary about these seemingly predestined comedic soulmates.

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There’s also some equally heady stuff to consider here about what happens when “rebels in sweaters,” as Smigel lovingly calls them, try to subvert things from the inside—and there’s comfort in Too Funny To Fail’s reassurance that huge, embarrassing commercial failure is so often the price of true creative freedom and, eventually, cult success. The Dana Carvey Show’s legacy as a farm team for all those future superstars definitely gives it that kind of moral certainty, borne out by the fact that several of its subjects—most glaringly CK, Kaufman, and Stamatopoulos—were apparently too busy and famous now to participate. (Although CK does appear in archival interviews.) Greenbaum further backs up his argument for The Dana Carvey Show’s revolutionary bona fides through testimony by mega-fans like Bill Hader, who recalls buying a VCR just to tape it, and Spike Feresten, who says he was so inspired by the show’s bleak, Beckettian “Grandma The Clown” sketch that he briefly left Seinfeld to go write for it.

Of course, it’s not all sunshine and dying old ladies. Everyone here is equally honest about their mistakes and regrets, of which there are many. Smigel discusses how, after finally getting around to watching Home Improvement, he was “horrified” at what they’d forced on its audience. Colbert and Carell uneasily recall starring in “possibly the most racist sketch ever committed to tape,” an Oscars parody that featured Carell, Carvey, and Smigel playing Indian, Asian, and Arabic stereotypes. And Greenbaum brings in both some of the critics who panned the show’s shaky early outings and the exasperated ABC executive who tried keeping it all afloat, even as the writers wrote sketches mocking him and their corporate sponsors—sponsors like Mountain Dew, who, y’know, would have preferred it if the show didn’t imply that their product looked like piss, thanks. These guys have a point, too: Fun and funny as it may be, you can only get away with saying “fuck you” for so long without the popularity to back it up. And really, Dana Carvey got to say fuck you for a lot longer than anyone else would have. In many ways, Too Funny To Fail captures a time when television was actually more willing to take those kinds of risks and abuse.

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And ultimately, of course, its brief lifespan worked in The Dana Carvey Show’s favor. Its punk-rock edge gets to remain forever preserved, never blunted by the kind of middle-age bloat that inevitably settles in on comedy shows. It certainly wouldn’t be the subject of these kinds of glowing documentaries, the length of which is nearly half the actual series’ collective runtime. (Again, you could also just go watch it.)

Besides, as Too Funny To Fail attests, nearly everyone ended up better off when it was dead. Carvey got to return to his family and his Wayne’s World royalties, and he seems totally at peace with both the show’s legacy and the comforts of his ongoing stand-up career. Smigel returned to Conan and SNL with The Ambiguously Gay Duo in tow, and he would go on to create his own cult successes in TV Funhouse and Triumph The Insult Comic Dog. As for Colbert and Carell—who both admit here that they’d have gladly done The Dana Carvey Show forever—it’s crazy to imagine what the past decade-plus of comedy would look like had they gotten their wish, or had the series not similarly loosed CK, Kaufman, Carlock, etc. to follow their own individual muses. “Every show deserves time to find itself,” Smigel says at one point. But what Too Funny To Fail suggests is that, in The Dana Carvey Show’s case, the best time for that was long after it was over.