Anderson was involved in filmmaking at a young age. As a high school student, he made the 30-minute mockumentary
The Dirk Diggler Story (1988), about a well-endowed male porn star (inspired by "Big"
John Holmes, who also served a major inspiration for
Boogie Nights).
After a brief stint as an English major at
Emerson College and an even shorter time at the
New York Film School, Anderson began his career as a production assistant on television movies, videos, and game shows in Los Angeles and New York. He later made
Cigarettes & Coffee (1992), a short with five vignettes set in a diner. The film was screened at the
1993 Sundance Festival, where it received considerable acclaim. In a few years, Anderson made his first full-length feature,
Sydney, which was retitled
Hard Eight (1996).
Anderson's breakout film
Boogie Nights, revisiting his Dirk Diggler character in a full-length major motion picture, was released on
October 10, 1997 to critical and commercial success. It was hailed by many critics as the "best film of the year, if not the decade", and is widely considered one of the finest depictions of the porn film industry. The film revived the careers of
Burt Reynolds and
Mark Wahlberg, and transformed
Julianne Moore into an A-list actress.
Anderson's next film was the ensemble piece
Magnolia (1999), which tells the story of the peculiar interaction among the lives of several individuals during a single day in the
San Fernando Valley, California. Interweaving nine separate yet connected storylines,
Magnolia was self-consciously produced with heavy
independent film influences (despite a large budget courtesy of
New Line Cinema), in a style quite distinct from that of mainstream
Hollywood films.
Magnolia was featured on over 150 critics top 10 lists of 1999, and received three
Academy Award nominations, for
Best Actor in a Supporting Role (
Tom Cruise), Best Original Song and
Best Original Screenplay.
Anderson returned with the
Comedy/Romance feature
Punch-Drunk Love (2002), starring
Adam Sandler. The story centers around a beleaguered small-business owner embarking on a romantic journey with a mysterious woman (
Emily Watson). Sandler won positive reviews for his role in his first major departure from the mainstream comedies which made him a star;
Roger Ebert wrote that "Sandler, liberated from the constraints of formula, reveals unexpected depths as an actor. Watching this film, you can imagine him in Dennis Hopper roles. He has darkness, obsession and power." Unfortunately, the film was not well received at the American box-office, grossing only $17 million despite a $25 million budget.
Anderson's next film,
There Will Be Blood is an adaptation of the
Upton Sinclair novel
Oil!. The novel is set during the oil scandals of the
Harding administration, and will provide a detailed depiction of the development of the oil industry in Southern California. The film will star
Daniel Day-Lewis.