Jay and Silent Bob Strike Back (2001)

When Jay (Jason Mewes) and Silent Bob (Kevin Smith) discover that the based-on-their-true-lives comic Bluntman and Chronic is being adapted into a movie without any licensing fees flowing their way, the duo heads for Hollywood to wreak havoc on the production. Along the way, they encounter just about every character from Smith's previous films, and Ben Affleck, Joey Lauren Adams, and Jason Lee each play two roles from past Smith movies. Matt Damon even pops up as good ol' Will Hunting, and there are more cameos than you can count.