- For the brief time he was at NYU film school, he handed in some of Pulitzer Prize-winner David Mamet's work as his own. When he got it back with a "C" grade he decided to leave.
- He dropped out of film school after the teacher in his first lecture claimed that anyone who wants to make a film like Terminator 2: Judgment Day (1991) should leave immediately.
- Tom Cruise got him on to the set of Eyes Wide Shut (1999). He spent the day there and got to talk to Stanley Kubrick.
- Despite the constant comparison between them amongst fans, he and fellow director Quentin Tarantino are great friends. Furthermore, Tarantino has praised Anderson's work, calling him a "filmmaking artist.".
- (As of 2018) The movie of his that he is the most proud of is The Master (2012).
- He is the only Director to win a best director prize at each of the big European film festivals. He won at Cannes for Punch Drunk Love, at Berlin for There Will be Blood, and at Venice for The Master.
- Cites Martin Scorsese, Robert Altman, Jonathan Demme, Stanley Kubrick, Orson Welles, and Max Ophüls as his main influences as a filmmaker.
- Cites Martin Scorsese and Jonathan Demme as his biggest influences and considers both to be the greatest American film directors.
- Has 4 children: daughters, Pearl Minnie Anderson (b. October 15, 2005) & Lucille Anderson (b. November 6, 2009), son, Jackson Wright "Jack" Anderson (b. July 3, 2011) and daughter, Minnie Ida Anderson (b. August 1, 2013) with girlfriend, Maya Rudolph.
- Directed 8 actors in Oscar-nominated performances: Burt Reynolds, Julianne Moore, Tom Cruise, Daniel Day-Lewis (twice), Joaquin Phoenix, Philip Seymour Hoffman, Amy Adams and Lesley Manville. Day-Lewis won the Best Actor Oscar for his performance in There Will Be Blood (2007).
- Dropped out of NYU's film program after two days. Subsequently got his tuition payment back and used the money to make Cigarettes & Coffee (1993).
- Once described Magnolia (1999) as "for better or worse, the best movie I'll ever make".
- His English teacher at Emerson College was renowned writer David Foster Wallace. Anderson has described him as the only teacher he ever loved, and stated in an interview with Marc Maron that his dropping out of Emerson College after a year was largely due to Wallace having left.
- Was described as 'his evil twin bother' by Daniel Day-Lewis when Day-Lewis was accepting the Critics' Choice Award for best actor for his performance in There Will Be Blood in 2008.
- He has a strong dislike of jokes about cancer after his father died from it.
- His favorite all-time film is The Treasure of the Sierra Madre (1948).
- Was employed as a standby director for A Prairie Home Companion (2006) for insurance purposes, and in the event that ailing 80-year-old director Robert Altman was unable to finish shooting.
- Sam Mendes calls him "a true auteur".
- Close friends with Christopher Nolan.
- Writes his screenplays in Microsoft Word. An assistant is hired to transfer these scripts into proper screenplay software for dispersal to crew during production, and receives on-screen credit in the finished film.
- Father, Ernie Anderson, was a local celebrity in Cleveland, where he hosted horror shows using the name "Ghoulardi".
- Attended Santa Monica College, Emerson College and New York University.
- Dated Fiona Apple from November 1997 to June 2000.
- He is a huge fan of Robert Downey Sr. and has cited him as a major influence.
- Lived in Los Angeles, USA with girlfriend Fiona Apple. He directed Apple in the video for her cover of "Across the Universe", which was part of the soundtrack for the movie, Pleasantville (1998).
- He had a difficult relationship with his mother which he has declined to discuss in interviews. It has been noted that the relationship between Dirk Diggler and his mother in Boogie Nights (1997) is a reflection of his own relationship, something that Joanna Gleason (who played Dirk's mother) mentioned to Anderson on set.
- Time magazine compared There Will Be Blood (2007) to "the greatest achievements" of D.W. Griffith and John Ford.
- Fan and personal friend of Aimee Mann. He used the song "Christmastime" performed by Mann in Hard Eight (1996), and many of her songs in the Magnolia (1999) soundtrack.
- In a relationship with Maya Rudolph since November 2001.
- He is a fan of comic book films, especially Christopher Nolan's Dark Knight trilogy.
- Anderson is one of Hollywood's "most infamously paranoid filmmakers," according to New York Magazine. "It's become part of Hollywood lore that Anderson, at least while represented by UTA, would never set foot in his own talent agency, and when he did contact his agent by phone, he would immediately demand that he call him back on his own cell phone, without any nosy assistants listening in." Anderson also "does not trust email" when sending out his screenplays, according to Lesley Manville. John C. Reilly said in an interview that Anderson prefers to be a "Wizard of Oz-like figure", hiding behind the curtain of his work.
- He has directed three films that have been nominated for the Best Picture Oscar: There Will Be Blood (2007), Phantom Thread (2017) and Licorice Pizza (2021).
- Attended Emerson College in Boston, Mass.
- Is a big fan of Adam Sandler and his movies.
- Is a big fan of Major League Baseball. His favorite teams are his hometown Los Angeles Dodgers and his late father's favorite team, the Boston Red Sox.
- Over the 7 movies he has directed/wrote; he has directed 7 actors to an Oscar Nomination. This equates to an Oscar Nomination for Acting for every movie he has made.
- Inducted into the Texas Film Hall of Fame on March 8, 2018 in Austin, Texas.
- He has expressed an interest in making a film adaptation of the DC Comics series Teen Titans.
- Got the initial idea for Hard Eight (1996) after watching Philip Baker Hall in Midnight Run (1988) according to a 2008 'Esquire' article: "In the summer of 1988, for example, when Midnight Run (1988) came out. It was a fairly formulaic action-comedy, and Martin Brest wasn't even close to Anderson's pantheon of cool directors, but one thing caught his eye: a little-known actor named Philip Baker Hall. In four very brief scenes, Hall plays a Las Vegas consigliere who keeps trying to convince his godfather not to whack people. His name was Sidney. "I don't think you should do this," he says in one scene. In another, he uses the curiously formal diction that seems to have hit Anderson in the place where he vibrates to the rhythms of David Mamet: "I'm supposed to advise you against such acts."".
- A longtime Thomas Pynchon devotee.
- Son of Ernie Anderson and Edwina Gough.
- He shaves his head before SOME productions. He did not shave his head before the production of Magnolia (1999), as evidenced in the documentary on the DVD.
- Many of his music videos double as camera and equipment tests for his upcoming films.
- He didn't attend film school.
- Born on the same date as Chris O'Donnell.
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