milestones
Year
Milestone
1975 
Acting debut as a guest on his mother's television series "Kate McShane" (CBS)
1976 
Began making Super 8 films at age 10
1985 
Made stage debut in the Broadway revival of John Guare's "The House of Blue Leaves"
1987 
Feature acting debut in Steven Spielberg's "Empire of the Sun"
1987 
Made a 10-minute short spoof of "The Color of Money" titled "The Hustler of Money"; aired on "Saturday Night Live" (SNL) in 1997
1987 
Hired as a writer on "Saturday Night Live" (NBC); had a brief stint as a featured performer in 1989
1987 
Appeared in PBS' "American Playhouse" production of "The House of Blue Leaves"
1989 
Created (also wrote and starred) the MTV sketch show "The Ben Stiller Show"; canceled after its first season
1992 
Created (also wrote, directed and starred) second sketch show, "The Ben Stiller Show"; aired on FOX; cancelled after one season
1994 
Feature directorial debut, "Reality Bites"; produced by Danny DeVito
1996 
Cast in a lead role in the hit comedy "Flirting with Disaster"
1996 
Helmed the commercially disappointing "The Cable Guy" starring Jim Carrey; first film with Owen Wilson
1997 
Signed to an exclusive contract with FOX; deal called for Stiller to establish a production company (Red House Productions)
1998 
Co-starred with Cameron Diaz in the sleeper hit "There's Something About Mary" directed by the Farrelly Brothers
1998 
Appeared in Neil LaBute's ensemble "Your Friends and Neighbors"
1998 
Offered a critically lauded performance as a heroin-abusing screenwriter in "Permanent Midnight"; Wilson had supporting role
2000 
Played a rabbi in love with the same woman (Jenna Elfman) as his priest pal (Edward Norton) in "Keeping the Faith"
2000 
Portrayed male nurse, Gaylord Focker in the box-office smash "Meet the Parents" opposite Robert De Niro; Wilson had supporting role
2001 
Co-starred with Owen Wilson, as rival male models in the comedy "Zoolander"; also directed and co-wrote
2001 
Portrayed the eldest child in a family of geniuses in "The Royal Tenenbaums"; Owen Wilson co-wrote screenplay with director Wes Anderson and co-starred as a family friend
2002 
Made cameo appearance as a firefighter in Jake Kasdan's "Orange County"
2003 
Co-starred with Drew Barrymore in the lackluster box office film "The Duplex"; directed by Danny De Vito
2004 
Starred as the risk-averse Reuben Feffer in the romantic comedy "Along Came Polly"; produced by Danny DeVito
2004 
Cast as Dave Starsky, opposite Owen Wilson as Ken 'Hutch' Hutchinson in Todd Phillips' spoof film adaptation of the 70's classic television show series "Starsky & Hutch"
2004 
Co-starred opposite wife Christine Taylor in the comedy "Dodgeball: A True Underdog Story"; also produced
2004 
Reprised role of Gaylord Focker in the successful sequel "Meet the Fockers"
2005 
Co-starred with Jeffrey Wright in the Neil LaBute play "This Is How It Goes" at the Public Theater in New York
2005 
Voiced Alex the Lion in his animated feature debut "Madagascar"
2006 
Earned an Emmy nomination for Guest Actor in a Comedy Series for his appearance on HBO's "Extras"
2006 
Played a night security guard in the family adventure, "A Night at the Museum"
2006 
Produced "Tenacious D in: The Pick of Destiny" starring Jack Black and Kyle Gass; also appeared in a cameo
2007 
Played the lead in the Farrelly brother's remake of "The Heartbreak Kid"
2008 
Directed and co-starred in the action comedy "Tropic Thunder"; also co-wrote and produced
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Lauren and Heidi of MTV's "The Hills"
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