I'm gonna cheat a little if you don't mind lmao
Movies:
1. Fantastic Mr. Fox
2. Napoleon Dynamite/Nacho Libre (The latter, I love everything BUT the toilet humor)
3. CB4 (Brilliant Commentary on the Rap Community and has a great soundtrack)
4. Kung Pow (I'm in love with everything but the CGI bits, the aliens, the tongue and the one chested lady. Probably the most creative film on this list)
And then there's other stuff like Tropic Thunder (I still can't believe they got away with what they did... Like Robert Downey Jr. was so committed to his character he did the VOICE DURING COMMENTARY)
TV Shows:
1. The Boondocks (Seasons 1-3)
2. The Simpsons (Seasons 1-16). Newer seasons feel neutered.
3. The Office (US Supremacy, WHOOP WHOOP!)
4. Smiling Friends
5. SpongeBob Seasons 1-3
Honorable mention is the Chappelle Show and Impractical Jokers. The latter is wild af. I use the reactions as resources for whenever I write my stories.
The Police Squad is also a great show. WKUK is another good one.
One show I've been meaning to get into is the Norm MacDonald Show. That dude is my favorite comedian.
Online:
The Onion (Porkin' Across America and Sex House are the most psychological shows I've seen online. They're horrifying. The first being a disturbing take on Kafka, the second being a criticism on shows like Jersey Shore)
OneyPlays
Redlettermedia
@Kuma ALSO HAPPY GILMORE. LOVE THAT MOVIE TO DEATH.