Ben Stiller, Will Ferrell, Penélope Cruz, Owen Wilson, and Kristen Wiig in Zoolander 2 (2016)

Robin Williams, Ben Kingsley, Ben Stiller, Brad Garrett, Owen Wilson, Steve Coogan, Patrick Gallagher, Ricky Gervais, Matthew Harrison, Randy Lee, Mizuo Peck, Darryl Quon, Jody Racicot, Gerald Wong, Dan Stevens, Anjali Jay, Skyler Gisondo, Rami Malek, Rebel Wilson, Kerry van der Griend, Paul Cheng, and Crystal the Monkey in Night at the Museum: Secret of the Tomb (2014)

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

Robert De Niro and Ben Stiller in Meet the Parents (2000)

Matthew Broderick, Téa Leoni, Eddie Murphy, Casey Affleck, Ben Stiller, Michael Peña, and Gabourey Sidibe in Tower Heist (2011)

Matthew Broderick, Téa Leoni, Eddie Murphy, Ben Stiller, Michael Peña, and Gabourey Sidibe in Tower Heist (2011)

Ben Stiller and Maria Bello in Permanent Midnight (1998)

Elizabeth Hurley, Ben Stiller, and Maria Bello in Permanent Midnight (1998)

Elizabeth Hurley and Ben Stiller in Permanent Midnight (1998)

Adam Sandler and Ben Stiller in Happy Gilmore 2 (2025)

Ben Stiller, Kym Whitley, and Sadie Sandler in Happy Gilmore 2 (2025)

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)

Ben Stiller in Saturday Night Live (1975)

Ben Stiller and Peter Greene in Permanent Midnight (1998)

Ben Stiller and Liz Torres in Permanent Midnight (1998)

Ben Stiller and Fred Willard in Permanent Midnight (1998)

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)