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 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.
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.
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.
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).
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.
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 - 13.
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 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.
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.
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."
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.
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.
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.
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.
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.
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.
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.
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.
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."
Newsday asked Renée Zellweger if it took her several tries to say the now-famous line correctly. "Cameron had me say it a few different ways," she said. "It's so funny, because when I read it, I didn't get it-I thought it was a typo somehow. I kept looking at it. It was the one thing in the script that I was looking at going, 'Is that right? Can that be right? How is that right?' I thought, 'Is there a better way to say that? Am I not getting it?' I just don't know how to do it."
The "Help me help you" line was a line first delivered by Kathy Bates in Misery (1990) 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.
Cameron Crowe felt that his film Singles (1992) hadn't done as well as he would've liked and wanted to write a more personal and emotional movie. "And all of a sudden I just looked around and-it was a good thing-many false friends disappeared," he told Paste in 2005. "And the people that sort of stayed behind, who you realize were your true friends and would be your friends for life, were not the people I expected. And that became one of the first ideas that drove Jerry Maguire (1996): what if you lost everything, or lost a lot, and you looked around and all those people that you thought would be there for life are gone. Who's left?"
A fan wrote into Cameron Crowe's website The Uncool and asked who was the inspiration behind Bob Sugar. Crowe told a story about how he was in Dublin in 1993, with Pearl Jam. He and the band were hanging out in a bar when Ronnie Wood walked in. Wood yelled to Crowe, "There's a guy who is stalking me, and he finds me wherever I go. I don't trust him, and he seems nice, but he scares me. He says his name is ... Bob Sugar! Bob Sugar! Can you believe it?" Later on, Crowe realized Wood was probably saying "Brown Sugar," as in the Stones' famous song, not Bob Sugar. But the name stuck. "When it came time to name the characters for Jerry Maguire (1996), Sugar was the first one on the page," Crowe said. "The perfect name for a nemesis-it rolled off your tongue with ease."
At the end of the movie, Roy Fisrestone interviews Rod Tidwell played by Cuba Gooding Jr who also plays O.J. simpson in the The people vs O.J.Simpson. In 1992 Roy Firestone interviewed the real O.J. Simpson.
During an appearance on Graham Norton's BBC talk show in 2012, Cuba Gooding Jr. talked about how his dad, Cuba Gooding Sr., didn't hold back on the set. Cuba introduced his dad to Tom Cruise, and his dad gave the actor a hug, then asked Cruise, "But seriously, are you gay or not?" Cuba later scolded his dad: "You can't keep your lips loose and they move too fast."
Jerry Maguire is flipping through the radio stations and finally starts jamming out to "Free Falling" after his meeting with Cushman. Even though he didn't know it at the time, Jerry was still in a "free fall".
Renée Zellweger auditioned 3 times with Tom Cruise and later received a personal call from Cameron Crowe while she was attending the Sundance Film Festival. Crowe thanked her for her time and she thanked him for being considered and just as the call was about to end Crowe asked, "Well do you want the job?".