Dead Parrot is a classic but so much so I don't think I can laugh at it anymore... or at least not without taking a break. It's brilliant but familiarity with sketches is tricky because for me it's often the smaller details are what make it. When I get some space, I'll forget the details and remember the premise and then it will be alive again.
Awesome list! This was a lot of fun.
Here's my list.
1.
Monster Mash (Mr. Show)
2.
Lie Detector (Mr. Show) - Mr. Show was all about mocking conventional comedy but they could do a classically structured sketch, like this one were a lie detector test inadvertantly reveals someone to be the most interesting person in the world. Also, I'm so used to Paul F. Tompkins being a smooth looking motherfucker, I forgot he used to look like every third character actor.
3.
Pre-Taped Call-In Show (Mr. Show)
4.
Skinner and the Superintendent AKA Steamed Hams (The Simpsons)
5.
Unfrozen Caveman Lawyer (Saturday Night Live) - Phil Hartman killed it but the joke is beyond the premise, it's that the unfrozen caveman lawyer pretends he's a man of the ancient people but he's an 80s Gordon Gecko style sleaze ball. A neanderthal Saul Goodman. But even more than that is my favourite thing; the non-sequitor sponsors. It's a shame I can't find the second one. "Brought to you by a square acre of Earthworms. What you do with them is up to you.
6.
Citizen Kane (Kids in the Hall) - I've been both characters in my life...
7.
Mayostard / Mustardayonnaise / Mustmayostardayonnaise (Mr. Show) - This is a great sketch series with ridiculous commercials... but it's so weird to see Jay Johnston, insurrectionist, as a gun-toting Lincoln in the second of the three. But it's like three great sketches that tell one weird story of food innovation.
8.
Oscar Wilde and Friends (Monty Python’s Flying Circus) I never disliked on it but I've slowly grown to appreciate the game of this one more and more. Seems like it would make for a fun improv game.
9.
Happy Fun Ball (Saturday Night Live) - I love this commercial very quickly swerving into cosmic horror.
10. Better Roots (w/ Bob and David) - I love it the same reason JBear does but my favourite part isn't the political commentary, it's the meta detail of the weird end credits decision which culminates a great bit. But many, it's kind of terrifying that this sketch is kind of ever green. "You know nothing about nothing to talk to nobody no-how, is that it?"
11.
Diner Wink (I Think You Should Leave) Diner Wink is funny but if anything it lives in my head because it is also kind of sad and sweet as a guy hi-jacks a dad's white lie to build a fantasy life for himself. It came at the right time; after Bob Odenkirk had that health scare, everyone latched onto this, demonstrating the actors strength.
12.
Blowing Up the Moon (Mr. Show) - I love this one and while I feel their is social commentary on completely pointless things to get excited about but I just love the goofiness.
13.
Hard Day (Kids in the Hall) - Fuck, David and Kevin are such a perfect comedy team. I love that Kevin likes to be a weirdly over the top straight man while David is a weirdo who has a "normal" cadence. "Look I didn't take this job to win any popularity contests." "OH YOU HAVEN'T!"
14.
Skoora the Gentle Shark (The Kids in the Hall) - The Kids don't often get to use all it's players in one sketch and it's not often to use them to this great effect. "I reached Woodstock on the second day of the Festival. Janice was in all her glory!"
15. Dead Parrot (Monty Python’s Flying Circus)
16.
Spanish Inquisition (Monty Python’s Flying Circus) - If there's something I love, it's villains who are not only ineffectual, they are accidentally helpful.
17. It’s Not Jackie Chan (Tim & Eric Awesome Show Great Job!)
18. The Day That Robert Palins Murdered Me (I Think You Should Leave)
19. Are We the Baddies? (That Mitchel and Webb Look)
20. Gun Genie (Picnicface)
21.
Continental Breakfast (Key and Peele) I also love characters getting way too excited about the banal and I love taking the idea of a fancy sounding continental breakfast and making someone enjoy it as if it was the most sublime treat.0
22.
It’s a Teardown (Comedy Bang Bang) - There's a big punchline it leads too but it's less of a sketch focused on a single premise and felt more like an excuse for 1) weird little jokes and 2) Scott Aukerman's love of terrible jokes, like his character having one joke that he refuses to deviate from. "Do you jack off to this or something?"
23. Space Lords (Human Giant) - Turns out making love on the son has it's disadvantages
24. Gravy Boat Lighthouse (Conan)
25.
Law School (Mr. Show) - Putting aside the fun coincidence to two of Better Call Saul's big lawyers discussing law, but this is all a fun play on lecture cliches in film and TV with a Twilight Zone twist. I don't know if this is a Paul F Tompkins written sketch but it feels like one of his.