Inspired by @bjnovak. Since you already listed some giants, I'm not including: Naked Gun, Wayne's World, and Ferris Buellers Day Off. I'm too skittish to rank or claim this is definitive- these are just some that have had a big impact on me through the years.
  1. Caddyshack
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    Because I saw this when I was young, too young, and with my older cousins who were cool in all things. Also, Rodney Dangerfield.
  2. Airplane!
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    A nod to the classics
  3. Moving
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    Because I grew up in a military family that moved every three years. One of our coping strategies was to pull this out and re-watch each time. We still quote it over 20 years later. And because there has to be a Pryor movie on the list! Great Dana Carvey performance as well, among many others.
  4. Monty Python and...
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    ...any of their movies. The triumvirate in junior high was Holy Grail, Life of Brian, and Meaning of Life.
  5. Trains, Planes and Automobiles
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    Classic road trip gone wrong. Another traveling themed one. Also seen while young and impressionable. Also Steve Martin. Also John Candy.
  6. Clerks
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    Hit me like a ton of bricks and opened my eyes in terms of what movies could be like. Don't always love Kevin Smith, but when he gets it right it's great.
  7. Groundhog Day
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    Profound and profoundly funny. Compelling in so many ways. Also Bill Murray.
  8. Bottle Rocket
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    My first Wes Anderson. Had no idea what to expect. Saw it alone at a campus theater after I found they were showing movies with cheap tickets and even cheaper popcorn. Don't always love Wes Anderson: other faves include Life Aquatic and Darjeeling Limited.
  9. I ❤️ Huckabees
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    I ❤️ this movie. Tried to explain it to a friend recently, very difficult. I love the philosophical elements; Mark Wahlberg in his best role ever; and Dustin Hoffman, of course!
  10. Cedar Rapids
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    Can't go wrong with Ed Helms. Another travel themed one I guess. Hilarious to me, and one that I enjoy re-watching when I can. I just love the journey!
  11. REAL LIFE - Albert Brooks' first feature. Brooks plays a documentarian who gets too involved with the family he's documenting. Satirized reality TV about 20 years ahead of time.
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    Suggested by @roche
  12. I cracked up every time I watched this as a kid. What a team!
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    Suggested by @jest
  13. Coming to America
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    Suggested by @amieshmamie
  14. Fletch
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    Suggested by @HisDudeness
  15. Saw this and Willow on a double feature with my dad.
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    Suggested by @k8zinker