1. THE CABLE GUY (1996)
Jim Carey's performance as a TV installer who lies, bribes and threatens his way into the life of one of his clients (Matthew Broderick) straddles comedy and menace. It shows Stiller's skill as a director of performance (he casts himself as a background presence in rolling news reports of a showbiz murder). Panned on release, it holds up surprisingly well as a depiction of loneliness in a world of 24/7 entertainment.
2. ZOOLANDER (2001)
The film that introduced Derek Zoolander and his trademark pout: ' Blue Steel'. A completely unpretentious comedy about very pretentious people, Zoolander worked because it was both affectionate and acerbic, reflecting most people's ambivalent attitudes to the hype of fashion.
3. REALITY BITES (1994)
Released the same year as Friends but largely forgotten, Winona Ryder, Janeane Garofalo, Ethan Hawke and Stiller star in what is a quintessentially Gen X movie about a group of college leavers in Houston. Its exploration of AIDS, job security and the corporatisation of youth culture isn't always subtle, but the film is heartfelt enough to want to cuddle. Plus there's a convenience store dance off to The Knack's 'My Sharona'.
4. ZOOLANDER 2 (2016)
It was never going to be easy following up the original, and too much of the satire seems stuck in the heyday of its main characters—the late '90s early '00s. It works, just, but given that shows like Portlandia have been satirising beards and craft-everything for a few seasons, Zoolander 2 needed its finger more firmly on today's pulse. (Read my Q&A with Stiller on his latest release here)
5. TROPIC THUNDER (2008)
While filming a war movie in South East Asia, a group of Hollywood actors stumble into a real combat zone. Great premise, great cast (Jack Black, Robert Downey Jr, Steve Coogan, Tom Cruise). But what should have been a rollicking film about the privileges and delusions of Hollywood never quite showed its teeth.
6. THE SECRET LIFE OF WALTER MITTY (2013)
Proof that Stiller should never stray too far from his black comedy instincts. The Secret Life of Walter Mitty is a little guy fable about learning to believe in yourself, the kind of dull idea and fantastical execution best kept for inspirational presentations at corporate retreats.