- Ability over Appearance: Cuba Gooding Jr. is on the small side for a football player, enough that the script was altered to discuss how his size is an issue; the Cardinals front office is worried that he's too undersized and vulnerable to injury and lowball him as a result despite his production, which forces Rod to play out his current small contract with the hopes he won't get hurt and cost himself money that's on the table. Funnily enough, this wouldn't even be the last time he played someone in the profession. It wouldn't be unprecedented for a player of his stature, however. For comparison sake, Cuba Gooding Jr. is 5'10, 170 pounds playing a wide receiver; Hall of Fame receiver Steve Smith Sr., who faced similar concerns early in his career, was a similar size at 5'9", 190.
- Cut Song: Aimee Mann's "Wise Up" was written for the movie but Cameron Crowe disliked the final version and didn't use it. Months later he called her up to tell her he had made a mistake, and so put the song on the official soundtrack. It also appears on the DVD version.
- Hey, It's That Place!: The baseball field in the end scene is the same one used for Jack's game in Hook.
- Hide Your Pregnancy: Regina King was legitimately pregnant during filming of the movie. It was written in for the second act, but you can see the tricks in the final scenes after Marcee has given birth. She's only shot from the chest up, has a lot of close-ups and wears a baggy jersey to hide the bump.
- Irony as She Is Cast: Bonnie Hunt joked about this, saying the hardest part of playing Laurel was that she had to pretend to hate Tom Cruise.
- Playing Against Type: Cameron Crowe's friends told him that Tom Cruise would "never play a loser." Turns out Cruise was dying to portray a character that was on the ropes.
- Reality Subtext: Cameron Crowe admitted the scenes of Jerry pleading with people were inspired by his own attempts to convince Pearl Jam to play at the infamous MTV promotional party for Singles.
- Real-Life Relative: Cameron Crowe's mother cameos in Laurel's group, as the woman who says "I finally got in touch with my anger."
- The Red Stapler: According to an ESPN Article written twenty years later, the movie inspired a lot of younger people to pursue careers as sports agents.
- Referenced by...: In 2003 film Shattered Glass, Stephen Glass's pitch of the fabricated "Hack Heaven" story involves his subject wiggling his hips in bravado while screaming "Show me the money!" One could argue that Glass used the film as inspiration for his fabrication (as it came out two years before his fall from grace).
- Revival by Commercialization: Bruce Springsteen's "Secret Garden" charted on the Billboard Hot 100 before when it was initially released to promote his Greatest Hits Album, but it only reached #63. After the song was featured in this film though, it was re-released in 1997 and reached #19 on the chart. It remains Springsteen's last top 20 hit to this day.
- Star-Making Role: For both Renée Zellweger and Cuba Gooding Jr., the latter of whom even won an Oscar.
- Throw It In!:
- Ray's famous line about the weight of the human head was something that Jonathan Lipnicki went around telling everyone on set. Cameron Crowe loved it and had him say it on camera.
- At one point during filming, Cameron Crowe heard that Cuba Gooding Jr was too small by the standards of most NFL receivers - so a line about Rod being too small was written into the film.
- While filming, Crowe came up with the idea of Jerry tripping and falling as he marches back to his office after getting fired. Cruise immediately agreed to the idea.
- Uncredited Role: Beau Bridges as Matt Cushman.
- What Could Have Been:
- Janeane Garofalo was told she would be cast as Dorothy if she lost weight. By the time she did, Renee Zellweger got the part. Winona Ryder was the first choice. However when screen testing her with Tom Cruise, producers felt they looked too much like brother and sister. Jennifer Lopez was offered the role, but turned it down on the advice of her agent. Connie Britton also tested for the role, and it was down to her and Zellweger. Patricia Arquette, Cameron Diaz, Bridget Fonda, Nicole Kidman (Tom's then-wife), Courtney Love, Parker Posey, Molly Ringwald, Uma Thurman and Marisa Tomei were also considered.
- Cameron Crowe wanted Billy Wilder to play the part of Dicky Fox, Jerry's mentor (seen in flashbacks), but despite both his and Tom Cruise's efforts, Wilder turned them down. Crowe wrote about the experience for Rolling Stone, which led to him writing a book about Wilder, so it didn't turn out too badly.
- Jennifer Connelly and Meg Ryan were each offered the role of Avery, but both turned it down. Diane Lane and Alyssa Milano were also considered.
- Crowe spent three years writing the script, and his initial choice for Jerry was Tom Hanks. By the time he finished writing, he felt Hanks was now too old for the part - not to mention also busy directing That Thing You Do. Edward Burns was the second choice, but he too was committed to directing. Tim Allen, Alec Baldwin, Johnny Depp, Sean Penn, Brad Pitt, John Travolta, Robin Williams and Bruce Willis were also considered.
- Jamie Foxx auditioned for Rod Tidwell. Damon Wayans and Mykelti Williamson were also considered.
- According to an interview with Cameron Crowe one year after the film's release, "So What" from the Stockholm concert with Davis and Coltrane was originally supposed to be the song that played during Jerry and Dorothy’s lovemaking session.
- "Where Are They Now?" Epilogue: The NFL created two A Football Life mockumentaries to commemorate the film's 20-year anniversary, showing:
- Frank Cushman retired from the NFL after only four years because of uncontrollable athlete's foot, and now works for charities assisting kids with the same affliction.
- Rod Tidwell was offered an even more lucrative contract, but turned it down in favor of spending more time with his family, saying the kwan just wasn't there.
- Ray now operates his own boxing gym in Los Angeles.
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