5. Tropic Thunder
The comedic star-power surrounding Stiller is great – Robert Downey, Jack Black, Danny McBride, McConaughey, Cruise, etc. and it also helps that he directed it.
The Simple Jack conversation and never going “full-retard” is a classic.
4. Starsky and Hutch
Underrated movie, granted I’m an Owen Wilson fan. Playing the moody, Napolean syndrome beta is a great roll for Stiller.
The coke dance-off gets me every time, especially the emphasis on “MY MAN DANCIN’ RICK!” and the following gun-pull
Another Owen Wilson movie?! You bet.
Over 15 years later and this movie is still regularly quoted by the sheeple which is a sign of staying power. This was also Will Ferrell’s coming out party as a star.
2. Meet the Parents
The everything-goes-wrong-for-Greg theme is so realistic and relatable. De Niro plays his part just as well as Stiller and of course, there’s a great appearance by Owen Wilson.
This grace scene is amazing, but honorable mention is the volley ball debacle.
1. Something About Mary
What can I say? This movie is a 10, one of those you can put it on at anytime and it’s always good movies.
Not only is this Stiller at his best, but Cameron Diaz too. Matt Dillon hasn’t done much, but “I work with retards” alone makes his performance stellar.
This scene is a bit over the top, but the lifeless body going out the window is an all-timer.
Honorable Mention: Along Came Poly, Cable Guy (kind’ve (definitely))