Also, if you're into musical things of the parody variety, check this out, performed and conceived by our dear friend Laura Kleinbaum!
8. Fuzz: The Musical (from Mr. Show)
Mr. Show did a few great musical sketches--in fact, there are a whopping TWO on this list. I think what made them so brilliant was the perfect blend of loving geekiness and mocking derision. These guys have clearly walked the boards a few times before, and you get the sense that they're simultaneously glad to be free from obnoxious musical theater types, but that they still sing songs from Into the Woods in the shower. (BTW, the best part of this clip is far and away David Cross' rendition of "How High the Mountain (Ronnie's Theme)" at about 3:40... if you prefer Patinkin to Cross, check this clip.)
7. Oh, Streetcar! (from The Simpsons)
I mean, come on... "The Kindness of Strangers" re-imagined as a big-budget, kick-line closer. Sign me up, The Simpsons.
6. Lease: The Musical (from Team America: World Police)
Consider yourself skewered, Rent! YOU WERE ASKIN' FOR IT! (Also, I'm sure glad we can all laugh at AIDS now.)
5. Red Ships of Spain (from Saturday Night Live)
Oh my gosh, does anyone remember this? Friggin' Goulet and his two brothers (Parnell and Baldwin)!!! AND I MANAGED TO FIND THE VIDEO!!!
4. Bye, Bye, Greasy (from Home Movies)
I think I have watched this episode of Home Movies more than any other one... thanks, Tom. This Grease/Bye, Bye, Birdie mash-up is a sublime catastrophe. (Coach McGuirk's song, around 4:15 in the video, is probably the highlight.)
3. Springtime for Hitler (from The Producers)
I mean, I can't not mention this. (The original, obviously...)
2. The Joke: The Musical (also from Mr. Show)
This has everything... a salesman selling leather pants in the Ozarks, pre-fame Jack Black as a farmer/devil, some holes in the wall, and best of all, a hated milk machine. This is the perfect end to the best Mr. Show episode EVER. (I CALLED IT JUST NOW.) Also, I love the looks on Bob and David's faces at the end, as the credits roll. They look positively giddy and thrilled... like they can't believe they actually got to pull that shit on National TV.
Part 2 (The Milk Machine Song!):
1. Red, White, and Blaine (from Waiting for Guffman)
Guffman is pretty much a perfect film. There are like, five Oscar-worthy performances in this film. Yes, actually, exactly five. And I think the icing on the cake (or the dressing on the salad?) is the musical itself. It's terrible, to be sure... but impeccably terrible. The songs are more than catchy, they're occasionally beautiful. (For instance, the one in this clip at about 1:00 in.) The whole production--like the town it tributes--is so sad and small, but these performers genuinely care about every note, every line... so even as an outside observer, you care can help but care, too.