Sideways

Back To The Future

Cinema Paradiso

Spaceballs

Up In Smoke (Cheech & Chong)

The Incredibles

Indiana Jones 1-3

Indiana Jones: Kingdom Of The Crystal Skull (Rifftrax only)

Falling Down

Office Space

Man Bites Dog

Nothing To Lose

Idiocracy

Space Mutiny (MST3k)

Goodfellas

Star Trek IV: The Voyage Home

Groundhog Day

Barbie

Full Metal Jacket

Mallrats

Flight Of The Navigator

The Founder

One Hour Photo

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I'm pretty certain I've rewatched Sideways more than any other film.