I know you wanted just five, but there are just so many.
Here's my top ten-
1. The Big Lebowski (1998) Coen Brothers
*ing Jeff Bridges, John Goodman, Steve Buscemi, Julianne Moore
"Dude" Lebowski, mistaken for a millionaire Lebowski, seeks restitution for his ruined rug and enlists his bowling buddies to help get it.
2. Office Space (1999) by Mike Judge
*ing Ron Livingston, Jennifer Aniston
Comedic tale of company workers who hate their jobs and decide to rebel against their greedy boss.
3. Forest Gump (1994) by Robert Zemeckis
*ing Tom Hanks, Gary Sinise
Forrest Gump, while not intelligent, has accidentally been present at many historic moments, but his true love, Jenny, eludes him.
4. Grosse Pointe Blank (1997) by George Armitage
*ing John Cusack, Minnie Driver, Dan Aykroyd
Martin Blank is a professional assassin. He is sent on a mission to a small Detroit suburb, Grosse Pointe, and, by coincidence, his ten-year high school reunion party is taking place there at the same time.
5. Groundhog day (1993) by Harold Ramis
*ing Bill Murray, Andie MacDowell
A weatherman finds himself living the same day over and over again.
6. Bowfinger (1999) by Frank Oz
*ing Steve Martin, Eddie Murphy, Heather Graham
When a desperate movie producer fails to get a major star for his bargain basement film, he decides to shoot the film secretly around him.
7. Four Rooms (1995) by Allison Anders & Alexandre Rockwell
*ing Tim Roth, Quentin Tarantino, Madonna etc.
Four interlocking tales that take place in a fading hotel on New Year's Eve.
8. Mafia! (1998) by Jim Abrahams
*ing Jay Mohr, Christina Applegate, Lloyd Bridges
Takeoff on the Godfather, Casino and other gangster films with the son of a mafia king taking over for his dying father
9. Trainspotting (1996) by Danny Boyle
*ing Ewan McGregor, Robert Carlyle
Renton, deeply immersed in the Edinburgh drug scene, tries to clean up and get out, despite the allure of the drugs and influence of friends.
10. The Birdcage (1996) by Mike Nichols
*ing Robin Williams, Gene Hackman, Nathan Lane
A gay cabaret owner and his drag queen companion agree to put up a false straight front so that their son can introduce them to his fiancé's right-wing moralistic parents.