It Came From Hollywood (1982)

A comedy documentary?  It's pretty shlocky, but before video stores, the internet, and Mystery Science Theater 3000, this was where I got my first look at the films of Ed Wood, and a ton of the classic bad movies that would become hipster touchstones in the nineties and beyond.

Directed by Malcolm Leo and Andrew Solt.  Written by Dana Olsen

Starring John Candy, Dan Ackroyd, Gilda Radner, Cheech and Chong.

With scenes from Plan Nine from Outer Space, Glen or Glenda, Blackbelt Jones, Maniac Reefer Madness, The Hideous Sun Demon, The Violent Years, some unbelievably racist piece of shit with Al Jolson, and so much more!  See the wikipedia article linked below for the complete list of films.

 
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Homicide: Life On the Street S1 E2 Ghost of a Chance

Directed by Martin Campbell Written by Paul Attanasio, Story by Tom Fontana.
Starring Kyle Secor, Yaphet Koto, Daniel Baldwin, Ned Beatty, and Richard Belzer
Originally broadcast Feb 3, 1993

 Rookie Homicide Detective Tim Bayliss feels the awesome responsibility of solving his first real case as primary detective: the brutal murder of 14 year old Adina Watson.

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MST3K: The Sinister Urge (1960)

From now on, Saturday is Mystery Science Theater 3000 day, and I'm starting with an Ed Wood masterfece.

Written and Directed by Ed Wood
 with a short, Keeping Clean and Neat (1956)
 Originally broadcast on Comedy Central November 5, 1994


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Frank Zappa's 200 Motels (1971)

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A series of surreal vignettes about how "Touring can make you crazy".

Written and directed by Frank Zappa and Tony Palmer.  Starring The Mothers of Invention, Theodore Bikel, and Ringo Starr.

A generous sampling: