Check out Photos from the Premiere of Jerry Maguire, 20 Years Later
Though he was into spilling facts (the human head weighs 8 lbs.!) in the film, these days, Lipnicki has other interests. "I'm really into jiu jitsu," Lipnicki told PEOPLE in 2011. "I'm a purple belt. I love it. It's a big part of my life. I'm so in love with martial arts, so [I'd want to do] something with that."
Jerry Maguire was Renée Zellweger's breakout role — she was actually selected for it by Cruise. Since then, she's earned a slew of starring roles and accolades, most notably the lead in the Bridget Jones series and an Oscar for her work in Cold Mountain.
Cuba Gooding Jr., who won a Best Supporting Actor Oscar for his role in the film, most recently won critical acclaim for his portrayal of O.J. Simpson in American Crime Story.
Though Jay Mohr (with then-wife Nicole Chamberlain) had been on Saturday Night Live and kicked around the stand-up comic circuit, Jerry Maguire was his feature film debut.
The other Jerry of Maguire, Jerry O'Connell played a star quarterback in the film. These days, he dabbles in TV and is married to Rebecca Romijn, with whom he has two daughters.
Bonnie Hunt, who portrayed Zellweger's sister, has transitioned into voiceover work lately, appearing in Zootopia and several Pixar films.
Regina King (with then-boyfriend Ian Alexander), who played Gooding Jr.'s wife in the film, picked up an Emmy in 2016 for her work in American Crime.
Cruise was nominated for an Oscar for his work in the film, losing out to Geoffrey Rush for Shine (he did, however, nab a Golden Globe). Cruise and Kidman divorced in 2001, five years after Maguire.