My Boss's Daughter (2003)
When a young man agrees to housesit for his boss, he thinks it'll be the perfect opportunity to get close to the woman he desperately has a crush on – his boss's daughter. But he doesn't plan on the long line of other houseguests that try to keep him from his mission. And he also has to deal with the daughter's older brother, who's on the run from local drug dealers.
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Rent / Buy
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Cast
Ashton Kutcher
as Tom Stansfield
Christopher Ashton Kutcher (born February 7, 1978) is an American actor, model, producer, and entrepreneur. He began his acting career portraying Michael Kelso in the Fox sitcom That '70s Show (1998–2...
Tara Reid
as Lisa Taylor
Tara Reid (born November 8, 1975) is an American actress. She began her television career with several guest appearances on television shows such as Saved By The Bell: The New Class, Days of our Lives...
Terence Stamp
as Jack Taylor
Terence Henry Stamp (July 22, 1938 – August 17, 2025) was an English actor. After training at the Webber Douglas Academy of Dramatic Art in London he started his acting career in 1962. He has been ref...
Jeffrey Tambor
as Ken
Jeffrey Michael Tambor (born July 8, 1944) is an American actor and comedian. He is known for his television roles such as Jeffrey Brooks, the uptight neighbor of Stanley and Helen Roper in the TV sit...
Molly Shannon
as Audrey Bennett
Molly Shannon (born September 16, 1964) is an American actress and comedian. She was a cast member on the NBC sketch comedy series Saturday Night Live from 1995 to 2001. In 2017, she won the Film Inde...
Andy Richter
as Red Taylor
Paul Andrew "Andy" Richter (born October 28, 1966) is an American actor, writer, comedian, and late night talk show announcer. He is best known as Conan O'Brien's sidekick on each of Conan's talk show...
Director
David Zucker
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