Ben Stiller and Peter Greene in Permanent Midnight (1998)

Elizabeth Hurley and Ben Stiller in Permanent Midnight (1998)

Ben Stiller and Liz Torres in Permanent Midnight (1998)

Ben Stiller and Fred Willard in Permanent Midnight (1998)

Ben Stiller in Saturday Night Live (1975)

Ben Stiller in The Secret Life of Walter Mitty (2013)

Robert De Niro and Ben Stiller in 2000 MTV Video Music Awards (2000)

Ben Stiller and Stephen Colbert in The Late Show with Stephen Colbert (2015)

Robert Downey Jr. and Ben Stiller in Tropic Thunder (2008)

Ben Stiller and Crystal the Monkey in Night at the Museum (2006)

Danny Glover, Gene Hackman, Gwyneth Paltrow, Anjelica Huston, Ben Stiller, Luke Wilson, Jonah Meyerson, Kumar Pallana, and Grant Rosenmeyer in The Royal Tenenbaums (2001)

Ben Stiller in Night at the Museum (2006)

Alec Baldwin, Ben Stiller, and Stormy Daniels in Stormy (2024)

Hank Azaria, Janeane Garofalo, William H. Macy, Paul Reubens, Ben Stiller, Kel Mitchell, Melinda Sue Gordon, Wes Studi, and Jeff Lunn in Mystery Men (1999)

Patricia Arquette, Ben Stiller, John Turturro, and Adam Scott in Watch What Happens Live with Andy Cohen (2009)

Robert De Niro, Eddie Murphy, Ben Stiller, and Owen Wilson in Showtime (2002)

Robin Williams, Ben Stiller, Patrick Gallagher, Mizuo Peck, Rami Malek, and Crystal the Monkey in Night at the Museum (2006)

Ben Stiller, Patrick Gallagher, Mizuo Peck, and Crystal the Monkey in Night at the Museum (2006)

Hank Azaria, Janeane Garofalo, William H. Macy, Paul Reubens, Ben Stiller, Kel Mitchell, and Wes Studi in Mystery Men (1999)

Ben Stiller, Malin Akerman, and Michelle Monaghan in The Heartbreak Kid (2007)