[Charles Henrickson]

1930s:
A Night at the Opera (or Marx Brothers as a group)

1940s:
Arsenic and Old Lace

1950s:
Some Like It Hot

1960s:
Dr. Strangelove
(Runner-up: The Odd Couple)

1970s:
Monty Python and the Holy Grail
(Runner-up: Young Frankenstein)

1980s:
A Christmas Story

1990s:
The Big Lebowski
(Runner-up: What About Bob?)

2000s:
Mr. Bean's Holiday

[3catsanadog]

The Out of Towners - with Jack Lemmon and Sandy Dennis. Not the remake.

Clueless - just something about that movie that cracks me up.

Drop Dead Gorgeous is a hoot too.