Tropic Thunder (2008)

Tropic Thunder is a comedy lampooning the many war films over the years, where a bunch of actors is dropped in the middle of the jungle to fend for themselves. The star-studded cast that includes Ben Stiller, Jack Black, Robert Downey Jr., and Tom Cruise was critically-acclaimed but would have issues today for a few reasons.

While the movie is a satire of Hollywood itself, the subtlety of the commentary may be lost on many. The particular plot points that wouldn’t work today would be Ben Stiller vying for an Oscar for playing a mentally-challenged person, as well as Robert Downey Jr.’s portrayal of a character who was completely in blackface.