Suggestions by @ihollowood18
1,741 suggestions
Harold Ramis
as Director in Pineapple Express (1980s)
Bill Murray
as Red in Pineapple Express (1980s)
John Belushi
as Dale Denton in Pineapple Express (1980s)
Dan Aykroyd
as Saul Silver in Pineapple Express (1980s)
Steve Martin
as Private Miller in Pineapple Express (1980s)
John Travolta
as Angus Tully in The Holdovers (1970s)
Michael J. Fox
as Angus Tully in The Holdovers (1980s)
Matthew Broderick
as Angus Tully in The Holdovers (1980s)
Walter Matthau
as Paul Hunham in The Holdovers (1980s)
Jack Lemmon
as Paul Hunham in The Holdovers (1980s)
Peter Falk
as Paul Hunham in The Holdovers (1980s)
Ben Affleck
as Angus Tully in The Holdovers (1990s)
Gene Hackman
as Paul Hunham in The Holdovers (1990s)
Michael Caine
as Paul Hunham in The Holdovers (1990s)
Dustin Hoffman
as Paul Hunham in The Holdovers (1990s)
John Cleese
as Paul Hunham in The Holdovers (1990s)
Jake Gyllenhaal
as Angus Tully in The Holdovers (2000s)
Michael Pitt
as Angus Tully in The Holdovers (2000s)
Kieran Culkin
as Angus Tully in The Holdovers (2000s)
Albert Brooks
as Paul Hunham in The Holdovers (2000s)