Eric Stoltz's character in this film is Ethan Valhere. Stoltz also played a character named Valhere in Say Anything... (1989), also directed by Cameron Crowe.
Jann Wenner, who plays the character Scully, is the publisher of Rolling Stone Magazine, for which writer-director Cameron Crowe once worked.
When Jerry is helping Dorothy move, one of the boxes has the game Risk. In Almost Famous (2000), another Cameron Crowe movie, a box Anita's boyfriend is carrying when he is helping her move also has the game Risk.
Shortly before the movie's release, Detroit Lions head coach Wayne Fontes was fired. His brief role was not cut from the final edit of the film.
This was Tom Cruise's fifth consecutive $100-million-plus film, a new record.
The scene in which Jerry and Ray are talking in the living room for the first time, was completely adlibbed. Director Cameron Crowe wanted to create a genuine "feel" between the two and did so by not having a written dialogue for that particular scene.
Cameron Crowe has stated that Jerry's memo/mission statement was directly influenced by Jeffrey Katzenberg's tirade after leaving Disney.
Cameron Crowe wanted his hero, legendary film director Billy Wilder, to play Dicky Fox. Wilder had agreed to think about it, but on the first day of filming, Wilder refused to play the role. So Crowe took Tom Cruise to Wilder's office to try to convince him, and Wilder still said no. Later, Crowe and Wilder became friends and Crowe wrote a book about Wilder's life.
Two Paul McCartney instrumentals are used in the movie, "Momma Miss America" (during the airport montage) and "Singalong Junk" (during Jerry and Dorothy's first kissing scene on the porch), both from the 1970 album "McCartney". Cameron Crowe received McCartney's permission without ever having met him, instead sending a tape of the film to the latter's office. The two would actually meet for the first time five years later in L.A., and the result of that meeting was McCartney composing the title song to Crowe's movie Vanilla Sky (2001), which earned an Oscar nomination for Best Original Song.
Winnie Holzman, creator of "My So-Called Life" (1994), appears in scenes involving the divorced women's group. She's the one who says, "these holidays make me feel more divorced".
Cameron Crowe's mother appears among those attending the divorced women's group. She is the one who says, "I finally got in touch with my anger."
When Dorothy and Ray drop off Jerry at the airport and look at the family saying goodbye (a mother and child are seeing off the father), the three people shown are the stand-ins for Tom Cruise, Renée Zellweger and Jonathan Lipnicki who worked on the film.
Jonathan Lipnicki showed up on the set one day telling everyone that, "the human head weighs eight pounds". Cameron Crowe liked it so much he wrote it into the script.
Tom Cruise did not remember that Bonnie Hunt was in Rain Man (1988). At first he thought she was joking when she said they had worked together before.
Parker Posey was originally considered for the role of Dorothy Boyd.
Cameron Diaz was considered for the role of Dorothy Boyd.
Cameron Crowe offered the Dorothy Boyd role to Janeane Garofalo, if she could lose weight, but after trimming down, she learned that Renée Zellweger had won the part instead in what was to become a career-launching smash hit.
Mira Sorvino auditioned for the role of Dorothy Boyd.
Courtney Love was considered for the role of Dorothy Boyd.
The stock footage of the airplane taking off is the same stock footage that was used for the airplane take off sequence in Billy Wilder's film Avanti! (1972).
The song that Couch is playing when Jerry enters his hotel room on the night of the draft is "Something In The Way" by Nirvana.
Diane Lane auditioned for the role of Avery Bishop.
Cameo: [Rick Reilly] Sports writer holding a camera behind Jerry after Rod gets up after being "hurt".
The parts of Dorothy and Jerry were originally written for Winona Ryder and Tom Hanks. Hanks was unable to commit to the project due to his work on That Thing You Do! (1996). Ryder was able to commit, but when screen tests were done with Tom Cruise, they "looked like brother and sister" when standing together.
Renée Zellweger admitted that the day she was cast in this film, it had been so long since she had worked that when she went to an ATM, she did not have enough of a balance to make a withdrawal.
The baseball field at the end of the film is the same field used in Hook (1991).
Two lines from the film, "Show me the money" and "You had me at hello", are in the AFI's top 100 movie quotes (at numbers 25 and 52, respectively).
The movie's line "Show me the money." was voted as the #80 of "The 100 Greatest Movie Lines" by Premiere in 2007.
Artie Lange filmed a small role but his scene was deleted.
The song playing when Dorothy and Jerry first have sex is "Haitian Fight Song" by Charles Mingus. This is the answer to Jerry's question "What IS this music?".
John Travolta was considered for the role of Jerry Maguire.
Ranked #10 on the American Film Institute's list of the 10 greatest films in the genre "Sports" in June 2008.
The story for Jerry Maguire is reportedly based on real-life Orange County agent Leigh Steinberg (who actually makes a cameo in the film as Troy Aikman's agent, which he was in real-life too). Steinberg's ex-partner David Dunn tried to lure away many of Steinberg's clients, just as Jay Mohr's Bob Sugar does in the film.
Former NFL defensive back Tim MacDonald is credited to have come up with the phrase "Show me the money!" while he was a member of the Arizona Cardinals.
The role of Bob Sugar, Jerry's unethical archenemy (played by Jay Mohr) was allegedly based on the real-life sports agent Drew Rosenhaus, known for similar tactics.
Cuba Gooding Jr.'s character in the film is named "Rod Tidwell" and played for the Arizona Cardinals football team. Tidwell's name may be inspired by Bill Bidwell, the owner of the team for 45 years who oversaw the team's move from St. Louis to Arizona. He is thanked in the credits.
At one point in the film, Tom Cruise's character says, "That's truth. Can you handle it?", a reference to the famous line from A Few Good Men (1992), which also starred Tom Cruise.
The Cardinal - Cowboy game at the end of the movie was actually an ABC Monday Night Football game played on Monday December 25, 1995. In the movie the Cardinals won, in real life the Cowboys won 37 - 31.
At one point in the film, a poster of Janet Jackson, is seen hanging on a wall in Tee Pee's (Aries Spears's) room. Jackson reportedly read for the part of Marcee Tidwell, but lost it to her Poetic Justice (1993) costar Regina King.
Alyssa Milano auditioned for the role of Avery Bishop.
Renée Zellweger's famous line "You Had Me From Hello" served as the inspiration behind Kenny Chesney's 1999 single of the same name. In 2005, Chesney married Zellwegger, only to have it annulled after four months.