When Cuba Gooding Jr. first read for his part for the studio, he did so with Robin Williams, assuming that Williams was going to be playing the title role. However, Tom Cruise had already been hired and Williams was simply substituting as a favor.
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.
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.
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.
Renée Zellweger's famous line "You had me at 'hello'" served as the inspiration behind Kenny Chesney's 1999 single with the similar name "You Had Me From Hello." In 2005, Zellwegger married Chesney, only to have it annulled after four months.
Because Cameron Crowe took so long writing the screenplay, he felt his original choice to play the title character - Tom Hanks - was too old to play the part by the time the film was ready to be made. Besides, Hanks had just won back-to-back Oscars and was in the midst of directing That Thing You Do! (1996).
In the elevator scene when Jerry and Dorothy spot a man signing to his girlfriend and Dorothy translates it as "You complete me", the man appears to be using Pidgin sign (basically American Sign Language signs in English word order) or possibly a form of Manually Coded English. What he literally says is "You make me feel whole."
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.
At the end of the movie, while Rod Tidwell is being interviewed on TV, Jerry Maguire is congratulated by a lady. She is the Winter Olympic champion Katarina Witt. She is seen standing next to Leigh Steinberg, the inspiration for the the title character. Leigh Steinberg introduces Jerry to Troy Aikman in the movie.
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.
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.
Artie Lange filmed a small role but his scene was deleted. According to Lange in his memoir, Cruise yelled at him for not entering his scene quickly enough. Lange further discussed his displeasure at working on the film but praised Cameron Crowe for being nice and professional. When his scene was cut, Crowe personally called Lange to inform him. Lange later went onto praise Crowe for taking the time to call, despite his schedule.
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.
At one point in the film, a promotional poster for Janet Jackson's 1993 album, "Janet.", 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.
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.
When Dorothy is packing up for her move to San Diego, a RISK game is seen in a box being transported inside the moving truck. In the movie ALMOST FAMOUS (also directed by Crowe), when Anita, Williams' sister is loading up her boyfriends car for their move to San Francisco, a RISK game is again seen being transported in a box.
Cameron Crowe chose the world of sports agents as he felt it was an area that hadn't been really broached on film before. Also, because the industry is solely dedicated to money and he was interested in seeing if such qualities like love and honor could flourish there.
Reebok struck up a product placement deal with TriStar for $1.5 million which included the incorporation of a commercial for their products into the film. They were naturally very displeased when the film was released without the promised commercial and indeed with Cuba Gooding Jr.'s character at one point saying "Fuck Reebok!". Legal action was threatened - the commercial was subsequently reinstated for the film's television airings.
As of 2015, it holds the record for lowest gross by a #1 film at the weekend box office with just over $5.5 million in ticket sales. This feat was achieved during its 7th week of release, bolstered by renewed public interest after it received an Academy Award nomination for best picture.
Aimee Mann told DCist about the song 'Wise Up': "Well, I wrote it for Jerry Maguire. [Writer/director Cameron Crowe] really liked the demo, and then he didn't like the finished version, so he didn't put it in the movie. Then after the movie came out, he called me and said, 'I don't know what I was thinking! Your version is awesome. I guess I was just kind of attached to the demo.' So he put it on the soundtrack album. So it's there, and on the DVD, but it wasn't in the original release of the film."
As 'Cameron Crowe' worked on the film, he learned that Cuba Gooding Jr. was considered too small by the standards of most NFL wide receivers, so he wrote a line of dialogue into the script that refers to this.
Tom Hanks auditioned for the role of Joel in Risky Business (1983) and was later considered for the lead role of Jerry Maguire but lost out the roles of Joel in Risky Business and Jerry Maguire to Tom Cruise
The "Help me help you" line was a line first delivered by Kathy Bates in Misery when addressing James Caan's character. It's poignant in that fact that Jerry Maguire uses it when he's struggling to understand Rod Tidwell, hence going through some misery himself.