Either way, you might enjoy a documentary on Hulu about the show, Too Funny to Fail. It's a look back on the series, why a niche audience loves it to this day, how it assembled a ridiculous roster of up-and-coming talent, and just what the hell happened for it to implode so spectacularly.
If you're not in the know, it's worth pausing for a moment to point out just how many now-heavy-hitters were associated with The Dana Carvey Show. The cast included Steve Carell, Stephen Colbert, and Robert Smigel, among others. They all contributed to the writing, along with Charlie Kaufman, Jon Glaser, Dino Stamatopoulos, Spike Feresten (who left Seinfeld for this!), Robert Carlock, and Louis C.K.
You can watch the documentary for a thorough explanation of why a sketch show with all those comedians didn't work, but it boils down to the same recipe that has made many a cult favorite: "no one is gonna tell US what to do... and what we do is only going to appeal (deeply) to a narrow audience." Too Funny to Fail shows a lot of great clips from the show -- some truly hilarious, some that hit you more in a "this is funny, even though I'm not laughing out loud" sort of way.
The documentary itself is also pretty funny, though. This really shouldn't be surprising, given that they're interviewing a lot of very funny people who use the opportunity to do bits for the documentary team. But the movie itself is edited in a wry and clever way, full of snarky on-screen captions and hilarious juxtaposition. (The biggest laugh in the entire documentary comes when they show an actual commercial that aired in 1996, for a "very special" Home Improvement episode, followed by a new Dana Carvey Show. The reactions are priceless.)
I don't know that this film is really going to the heart of what's funny and why -- or even if one documentary should shoulder the burden of asking that. But it's a great examination of creative minds at work (and play). They thought it made sense at the time, they mostly seem to stand by it now, and if you're the sort of person who would make time for this documentary, you'll probably get that.
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