Jerry Maguire cast - Where are they now? | Gallery

By Megan Riedlinger 3:00am PST, Dec 2, 2016

It's been two decades since Cuba Gooding Jr. first shouted "Show me the money!" in the beloved Cameron Crowe-directed flick "Jerry Maguire." In honor of the film's 20th anniversary on Dec. 13, 2016, Wonderwall.com is taking a look at where its stars are today! Keep reading to find out…

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Tom Cruise played the titular role of Jerry Maguire, the slick sports agent who has an epiphany and writes an epic mission statement about the way he thinks business should be done. After starting his own company and struggling to find success again, he redefines his relationships with his clients, the woman he loves and himself.

The same year "Jerry Maguire" was released, one of Tom Cruise's most iconic characters to date also made his debut: Ethan Hunt in "Mission: Impossible." That movie franchise has continued to thrive for the last two decades, with the most recent flick, "Mission: Impossible – Rogue Nation" hitting theaters in 2015. But Tom has also starred in plenty of other profitable movies, ranging from science fiction films like "Vanilla Sky" in 2001 to the disaster flick "War of the Worlds" in 2005. He was named the highest-paid actor in 2012 and has continued to enjoy a rare, lasting success in Hollywood. He'll next appear in the summer 2017 action flick "The Mummy." While shooting "Jerry Maguire" Tom was still married to Nicole Kidman, his second marriage at that point (he was previously married to actress Mimi Rogers). They adopted two children, Connor and Isabella, but ultimately split in 2001. In 2006, he famously wed Katie Holmes, with whom he shares 10-year-old daughter Suri. The duo divorced in 2012, and though Tom has been linked to many ladies since then, he has yet to have a serious relationship post-Katie.

Renee Zellweger charmed audiences as single mom Dorothy Boyd, who eventually becomes Jerry Maguire's love interest. The role helped launch her career and netted her a Screen Actors Guild Award for Outstanding Performance by a Female Actor in a Supporting Role.

Renee Zellweger's career continued to thrive as the star landed the coveted lead role in 2001's "Bridget Jones's Diary" and enjoyed critical success in 2003 for her performance in "Cold Mountain," for which she won a Golden Globe, a Screen Actors Guild Award and an Oscar. The actress took a six-year hiatus from acting in 2010 and returned to the big screen in 2016 with "Bridget Jones's Baby." Renee was engaged to Jim Carrey from 1999 until 2000, but they never made it down the altar. The actress wed Kenny Chesney in 2005, but they annulled their marriage after only four months. Renee has been dating musician Doyle Bramhall II since 2012.

Jonathan Lipnicki played Dorothy's adorable son Ray Boyd. Thanks to this darling kid, we learned plenty of fun factoids — like exactly how much the human head weighs. The role made Jonathan one of the go-to child stars of the decade.

Since playing Ray in 1996, Jonathan Lipnicki has stepped in and out of the spotlight. He followed up "Jerry Maguire," which was his first role ever, with parts in "Stuart Little" and "Stuart Little 2" and stints on popular television shows like "Dawson's Creek" and "The Jeff Foxworthy Show." Though there have been some gaps in his acting résumé, Jonathan has steadily worked over the last two decades, most recently on the 2016 show "Interns of F.I.E.L.D." He also has a purple belt in Brazilian jiu-jitsu and is a sparring partner for MMA fighters.

Jay Mohr portrayed Bob Sugar, Jerry Maguire's former protégé , who ultimately gets tasked with firing him after Jerry shares his new mission statement with his company, the sports management firm Sports Management International. Once Jerry moves on, Bob attempts to keep his clients signed to SMI, stealing one of Jerry's biggest prospects, Frank "Cush" Cushman.

After playing the unlikable Bob Sugar in "Jerry Maguire," Jay Mohr appeared in 1997's "Picture Perfect" and 1998's "Paulie" and "Small Soldiers." He enjoyed success on the small screen, voicing a character on "Family Guy" from 2000-2005, and starred on "Suburgatory" from 2011 until 2013. Most recently, Jay has been lending his voice to the Netflix animated show "BoJack Horseman." In July 2016, he and his wife of nine years, writer-actress Nikki Cox, filed for divorce. They share a 5-year-old son, Meredith. Jay also has a son, Jackson, from his previous marriage to model Nicole Chamberlain.

Cuba Gooding Jr. played Rod Tidwell, an Arizona Cardinals wide receiver and one of Jerry's first clients after he started his own firm. His character delivers the infamous line "Show me the money!" after Jerry fails to secure a contract. Cuba's performance earned him an Academy Award for Best Supporting Actor.

After "Jerry Maguire," Cuba Gooding Jr. suffered some blows at the box office. He had a string of flops, including 1999's "Chill Factor," 2002's "Boat Trip" and 2007's "Norbit" and "Daddy Day Camp." He enjoyed a career revival more recently when he earned critical raves for his performance as O.J. Simpson on 2015's "American Crime Story: The People v. O.J. Simpson." Cuba married his high school sweetheart, Sara Kapfer, in 1994, two years before the release of "Jerry Maguire." They share three kids: Spencer, Mason and Piper. Sara filed for divorce after two years of marriage in 2014.

Regina King portrayed Marcee Tidwell, Rod's outspoken wife, in a role that helped establish her career. Prior to "Jerry Maguire," she was known mainly for her role on the NBC comedy "227."

Since starring in "Jerry Maguire," Regina King has continued to have a successful film and television career. She starred in films like "How Stella Got Her Groove Back" and "Mighty Joe Young" in the '90s, and in the '00s had a role on the hugely popular television show "24." The following decade saw more success for Regina on the small screen as she starred on the critically acclaimed "Southland" from 2009 to 2013 and dropped in for smaller roles on hits like "The Big Bang Theory." In 2015, she joined the cast of ABC's "American Crime" — and won two Emmys for her work on the anthology series. "I've been so busy with work and my girlfriends are like, 'Do you think a man is just gonna go knock on the door, like, 'I'm here!'?' And I think I wish he would, but I have to make that more of a priority," Regina told Wendy Williams during a 2015 appearance on "The Wendy Williams Show." (From 1997 to 2007, she was married to Ian Alexander, with whom she shares a son, Ian Jr.)

Before Jerry Maguire moved on with Dorothy, he was in a relationship with Kelly Preston's character, Avery Bishop. Avery lacked that "sensitivity thing," which ultimately led to the couple's demise.

"Jerry Maguire" remains one of Kelly Preston's most notable roles to date. She also played the girlfriend of her real-life husband John Travolta's character in 2000's "Battlefield Earth," which earned her the esteemed Golden Raspberry Award for Worst Supporting Actress that year. She's also taken on a few small-screen roles on shows like "Joey" in 2004 and "Fat Actress" in 2005 and most recently did a stint on "CSI: Cyber" in 2016. She and John have been married since 1991. They've welcomed three children together: daughter Ella and sons Benjamin and Jett, who died suddenly in 2009.

Jerry O'Connell took on the role of star quarterback Frank "Cush" Cushman, the player who reneged on his deal with Jerry Maguire and ended up signing with Jerry's rival Bob Sugar. Before his role in the 1996 film, Jerry was best known for his work on the television show "Sliders" and in the classic 1986 film "Stand By Me."

Jerry O'Connell found success on the small screen after "Jerry Maguire" debuted. The actor starred on the NBC drama "Crossing Jordan" from 2002 to 2007 and on NBC's "Las Vegas" from 2004 until 2006. After that, he had roles on shows such as "The Defenders" from 2010 to 2011 and voiced a character on "Jake and the Never Land Pirates" from 2013 to 2015. In 2016, he joined the cast of "Scream Queens" as Dr. Mike. In 2007, Jerry married model Rebecca Romijn, with whom he shares 7-year-old twin daughters Dolly and Charlie.