Jerry Maguire cast - Where are they now? | Gallery

By Megan Riedlinger 5:25am PST, Dec 13, 2021

It's been nearly three decades since Cuba Gooding Jr. first shouted "Show me the money!" in the beloved Cameron Crowe-directed flick "Jerry Maguire." In honor of the Tom Cruise film's 25th anniversary on Dec. 13, 2021, Wonderwall.com is taking a look at where its stars are today!

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Tom Cruise played the titular role of Jerry Maguire, a 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 sequel, "Mission: Impossible – Fallout," hitting theaters in 2018. But Tom has also starred in plenty of other profitable movies since "Jerry Maguire" ranging from the 2001 sci-fi flick "Vanilla Sky" to the 2005 disaster film "War of the Worlds" to the 2012 and 2016 "Jack Reacher" action movies. Tom, who was named the world's highest paid actor in 2012, has continued to enjoy a rare, lasting success in Hollywood that will next see him star in 2022's "Top Gun: Maverick," 2022's "Mission: Impossible 7" and 2023's "Mission: Impossible 8." Tom ended his marriage to second wife Nicole Kidman in 2001. After dating Penelope Cruz, he wed Katie Holmes in 2006 several months after they welcomed daughter Suri. Katie left him in 2012. Tom has yet to go public with a romance since then, though he was rumored to be dating "M:I 7" co-star Hayley Atwell during production.

Renee Zellweger charmed audiences as single-mom assistant 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 lead role in 2001's "Bridget Jones's Diary" and enjoyed critical success for her performance in 2003's "Cold Mountain," for which she won a Golden Globe, a Screen Actors Guild Award and an Oscar. The actress began a six-year hiatus from acting in 2010 and returned to the big screen in the 2016 sequel "Bridget Jones's Baby." She's since starred in the Netflix miniseries "What/If" and the 2019 biopic "Judy," a performance that earned her Academy, Golden Globe, SAG, BAFTA and Critics' Choice awards for best actress. She'll next appear in the crime-drama series "The Thing About Pam." Renee was engaged to Jim Carrey from 1999 until 2000, but they never made it down the aisle. A romance with the White Stripes rocker Jack White followed, then Renee wed Kenny Chesney in 2005, only to have their marriage annulled four months later. After dating Bradley Cooper, she spent seven years with musician Doyle Bramhall III. In 2021, Renee and English TV host Ant Anstead — the car builder and motor specialist ex-husband of "Flip or Flop" star Christina Haack — took their romance public.

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" — his first movie — with parts in "Stuart Little" and "Stuart Little 2" and stints on popular television shows like "Dawson's Creek" and "The Jeff Foxworthy Show." He's also appeared on TV and web shows and though there have been some gaps in his acting resume, Jonathan has worked steadily over the last two decades, albeit usually in small projects including, more recently, the 2021 film "Pooling to Paradise." He also has a headline-making hobby: Jonathan earned a black belt in Brazilian jiu-jitsu and has been 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, 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 to 2005, and starred on "Suburgatory" from 2011 until 2013. He's since lent his voice to a character on "BoJack Horseman" and appeared on television shows including "The Mick" and "American Housewife." He'll next appear on the 2022 crime-drama series "The Cleaning Lady." Jay and his wife of nine years, actress Nikki Cox — with whom he shares son Meredith, who was born in 2011 — split in 2016 and lter divorced. 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 who becomes one of Jerry's first clients when the sports agent starts his own firm. Cuba's character delivers the infamous line "Show me the money!" after Jerry fails to secure a contract. His 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 when he earned critical raves for his performance as O.J. Simpson on 2016's "American Crime Story: The People v. O.J. Simpson." That same year, he also appeared in the sixth season of "American Horror Story." Cuba formally split from high school sweetheart Sara Kapfer, with whom he has three kids, in 2014 after more than 20 years of marriage. He's been linked to several women since, including Robert De Niro's former daughter-in-law Claudine. He's made headlines in recent years not for his acting but for his alleged bad behavior: More than two dozen woman have come forward with sexual misconduct allegations in recent years — and some have filed civil lawsuits against him. The actor is also facing criminal charges in multiple cases. He's maintained his innocence, and litigation is ongoing.

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

Regina King went on to star in films like "How Stella Got Her Groove Back" and "Mighty Joe Young" in the '90s. In the '00s, she had a role on the hugely popular television show "24." The following decade saw even more success for Regina as she starred on the critically acclaimed cop drama "Southland" from 2009 to 2013. In 2015, she joined the cast of ABC's "American Crime" and won two Emmys for her work on the anthology series. In 2018, she won another Emmy for her work on "Seven Seconds" and delivered an Oscar-winning performance in the Barry Jenkins-directed movie "If Beale Street Could Talk." She then won her fourth Emmy in 2020 for her work on HBO's critically acclaimed limited series "Watchmen." Regina had two films debut in 2021: "Flag Day" and "The Harder They Fall." From 1997 to 2007, she was married to Ian Alexander, with whom she shares a son, Ian Jr.

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 addition to having a three-episode arc on "The Big Bang Theory" from 2018 to 2019, Jerry landed a starring role on the Canadian crime-comedy series "Carter" in 2018. Since 2020, he's voiced Commander Jack Ransom on "Star Trek: Lower Decks," and in 2021, he replaced Sharon Osbourne to become the first male co-host on "The Talk." In 2007, Jerry married model Rebecca Romijn, with whom he welcomed twin daughters Dolly and Charlie in 2008.

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.

After "Jerry Maguire," Kelly Preston went on to play the girlfriend of real-life husband John Travolta's character in 2000's "Battlefield Earth," which earned her the esteemed Golden Raspberry Award for worst supporting actress. She also appeared in a few TV roles on "Joey" in 2004 and "Fat Actress" in 2005 and did a stint on "CSI: Cyber" in 2016, though her favorite job was being a mom to her and John's three kids: son Jett, who died in 2009; daughter Ella — who was born in 2000 and is now an actress — and son Benjamin, who was born in 2010. In 2020, Kelly died after a private two-year battle with breast cancer. She was 57. Her final film, "Off the Rails," was released posthumously in 2021.