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The Cable Guy (1996)
This underrated, very dark comedy is about a cable customer (Matthew Broderick) harassed by a friendless technician (Jim Carrey) who seems to have bubbled up from the very id of television itself. Sorta like child-of-pop-culture Stiller, who famously grew up in a caustic showbiz household as the son of comics Jerry Stiller and Anne Meara.
Stiller directed and starred in this classic satire of the fashion world, playing a vacuous model-turned-Manchurian Candidate-style unwitting assassin. Bonus points for naming its villain, Mugatu (Will Ferrell), after an old Star Trek monster.
Tropic Thunder (2008)
It took 20 years for Stiller to turn his failed Platoon audition into this merciless satire about pampered Hollywood actors (Stiller, Jack Black, and Robert Downey Jr.) whose Vietnam War epic goes violently awry.
Image Credit: Merie Weismiller Wallace
August 18 2008 — 12:00 AM EDT