Are you ready to hear some news that may make you feel a bit old? Well, ready or not here it is: Jerry Maguire turns 20 this year! That is right, the romantic classic that had us all at hello is about as old as a majority of college students out there. That being said, quotes such as “show me the money” and “do you know that the human head weighs eight pounds?” remain as timeless as ever.

This endlessly quotable movie not only featured fantastic writing, but a stellar cast as well. From the obvious Tom Cruise, Renée Zellweger, and Cuba Gooding Jr. to Regina King, Jerry O’Connell, and more, several of the film’s actors remain fairly active in Hollywood today. As this Best Picture nominee turns 20-years-old, we take a look at the movie’s biggest stars and see what they have been up for the past two decades.

Here is Where Are They Now? Cast Of Jerry Maguire

10. Tom Cruise (Jerry Maguire)

Tom Cruise Then and Now Where Are They Now? The Cast Of Jerry Maguire


Jerry Maguire was a successful, 35-year-old sports agent until a late night, life-altering epiphany found him constructing a 25 page mission statement that featured ideals such as: fewer clients, less money, and more attention and care towards the respective athletes. As a result, Sports Management International (SMI), the firm that Jerry worked for, fired the young idealist and as a result, he began his quest to start his own agency.

Tom Cruise’s acting career since his role in Jerry Maguire is no secret, as the three time Oscar-nominated actor has served as one of Hollywood’s premiere movie stars since Top Gun in 1986. In addition to his Best Actor consideration for his work on Jerry Maguire, he has since been nominated for his efforts in the 2000 Paul Thomas Anderson directed film Magnolia. Additionally, Cruise has gone on to star in Eyes Wide Shut, Minority Report, War of the Worlds, The Last Samurai, Edge of Tomorrow, and four more Mission: Impossible movies since portraying Maguire. The 53-year-old actor shows no signs of aging either, as he is slated for several upcoming blockbusters, such as: Mission: Impossible 6, Jack Reacher: Never Go Back, and of course The Mummy reboot, which is slated to birth an entire monster movie cinematic universe.

9. Todd Louiso (Chad the Nanny)

Tom Louiso Then and Now Where Are They Now? The Cast Of Jerry Maguire


Chad the Nanny – actually he perfers “child technician” – is a peculiar character of sorts. As the babysitter of Dorothy’s son, Ray, he only plays a minor role in this film, but when he was on screen, he was usually good for a laugh or two. Even after all of these years, he is remembered for his off the wall monologues, and his love for Miles Davis and John Coltrane, also known as the “two masters of freedom.”

A bit quietly, Todd Louiso has managed to hang around Hollywood, and fairly consistently find work. He may not have the number of top billings in major blockbusters that Cruise has, but Louiso has played his share of supporting roles in several films over the past two decades: High Fidelity, School For Scoundrels, The Switch, Snakes on a Plane, xXx: State of the Union and Thank You for Smoking. In addition to his acting filmography, Louiso boasts numerous guest appearances on several critically praised and award winning television shows such as House M.D., Without a Trace, Californication, NCIS, and Frasier to name a few.

Not to mention, Todd Louiso is also beginning to make a name for himself as a screenwriter and director. He currently has three feature length films to his credit as a director and is credited for penning the screenplay of last year’s Shakespeare adaptation Macbeth, starring Michael Fassbender and Marion Cotillard.

8. Kelly Preston (Avery Bishop)

Kelly Preston Then and Now Where Are They Now? The Cast Of Jerry Maguire


In the picture of Jerry Maguire’s former ideal life, we see the premiere job, the fancy car, the big house, and the beautiful girlfriend. The aforementioned girlfriend was none other than Avery Bishop, an unsympathetic, narcissistic woman with a wicked temper. Avery did not buy Christmas presents in advance, gush over babies, cry during movies, or even offer to try and console Jerry in the slightest when his life came crashing down around him. What ever that “sensitivity thing” is that some people have, well, it was clear that she did not.

Like clockwork, Kelly Preston has been averaging one to two movies (sometimes even more) just about every year since her appearance in Jerry Maguire. What a Girl Wants, Battlefield Earth, Jack Frost, Death Sentence, Sky High, Old Dogs, and The Last Song are only some of the more memorable movies she has been in over the past twenty years or so. In addition to her work on the big screen, the beautiful Kelly Preston has contributed supporting roles to numerous television series including Medium and CSI: Cyber. To this day, she remains happily married to John Travolta, and in November 2010, they celebrated the birth of the third child, Benjamin.

7. Jonathan Lipnicki (Ray Boyd)

Jonathan Lipnicki Then and Now Where Are They Now? The Cast Of Jerry Maguire


Ray was just about the most adorable little kid with his various “did you know” factoids, along with his other various encounters with the titular character, Jerry. Additionally, he served to complicate the relationship between Jerry and Dorothy as they began to fall in love and start up their own sports management agency. As a single mother, Dorothy was forced to consider the consequences of her actions and how it would end up affecting her son. Meanwhile, Jerry was forced to weigh his own emotions as it became more and more obvious that Ray began to see him as a father figure of sorts.

Jonathan Lipnicki looked to be one of the biggest child stars in the mid to late 90’s after the massive success that was Jerry Maguire. Within the next six years, Lipnicki would go on to star in both Stuart Little as well as its successor, Stuart Little 2, along with The Little Vampire, Like Mike, and Zachary Beaver Came to Town. Not long after however, the former child star decided that he wanted to resume his education in his hometown as a normal kid. This continued for some time, but soon the acting bug got a hold of him once again, as he started to appear in more and more roles in Hollywood. Since then, he has had some guest roles on popular television series – Monk and Family Guy – and is acting in a number of films slated for release in 2016.

6. Jay Mohr (Bob Sugar)

Jay Mohr Then and Now Where Are They Now? The Cast Of Jerry Maguire


As Maguire’s former protégé turned rival, Bob Sugar was almost a mirror image of everything that Jerry used to be, a hard-nosed, cut-throat, take no prisoners sports agent. Upon Jerry’s dismissal from Sports Management International, Sugar proceeded to kick him while he was down by recruiting all of his former clients, including the NFL’s number one overall draft pick, Frank “Cush” Cushman.

This former Saturday Night Live impersonator has done just about everything in Hollywood over the span of his career. Jay Mohr has been nominated for a Primetime Emmy and has guest starred in numerous hit sitcoms: The Simpsons, Family Guy, Scrubs, and Suburgatory. He has shown versatility by starring in both television dramas and various films: CSI: Miami, Small Soldiers, Pay it Forward, and The West Wing. Mohr has even become quite the voice actor in the video game sphere with contributions to titles such as Blitz: The League 2, Saints Row 2, and most recently, Saints Row: Gat Out of Hell.

5. Jerry O’Connell (Frank “Cush” Cushman)\

Jerry OConnell Then and Now Where Are They Now? The Cast Of Jerry Maguire


One of the clients that Jerry desired to keep after leaving his firm was the young star quarterback Frank “Cush” Cushman. Projected to go number one at the NFL draft, Jerry hoped that Cushman would remain faithful to their arrangement. Everything looked good for Maguire until he found out that “Cush” welched on their deal, and instead found representation elsewhere with his former protégé turned arch-rival, Bob Sugar.

Despite serving as one of film’s more minor characters, Jerry O’Connell has remained busy as a consistently working actor in Hollywood. Whether it be voice acting in animated series – Jake and the Neverland Pirates, The Batman, Justice League – contributing supporting and leading roles to television hits – Las Vegas, Crossing Jordan, The Defenders – or even appearing in popular sitcoms – The League, Workaholics, Drunk History, Young & Hungry, Burning Love – O’Connell has likely been apart of one of your favorite television shows in some capacity at one time or another. In addition to his work on television, the 42-year-old actor has also contributed to a number of feature films: Scream 2, Tomcats, Yours Mine and Ours, Veronica Mars, and the recent animated DC film, Justice League vs. Teen Titans.

4. Bonnie Hunt (Laurel Boyd)

Bonnie Hunt Then and Now Where Are They Now? The Cast Of Jerry Maguire


Laurel Boyd played the role of the overprotective, overbearing sister to Dorothy. Being the outspoken older sibling, Laurel was never afraid to make her thoughts and feelings known to Dorothy. Still, it was obvious that her heart was certainly in the right place. At the core of her concerns was always the well-being of her sister, as well as her nephew Ray. Laurel was very rarely without an opinion, and almost always chose to express it.

Bonnie Hunt is about as versatile as they come on this list. Since her role as Laurel Boyd, Hunt has gone on to voice act for various Pixar films: A Bug’s Life, Cars, Cars 2, Monsters Inc., Monster’s University, Toy Story 2, 3, and soon Toy Story 4. Also, she most recently voiced Bonnie Hopps in this year’s Disney animated hit, Zootopia. Hunt played a supporting role in the 1999 Stephen King adaptation, The Green Mile, and even produced, hosted, and wrote her own talk show, aptly named The Bonnie Hunt Show. Additionally, the talented actress has numerous producer, directorial, and writing credits to her name.

3. Regina King (Marcee Tidwell)

Regina King Then and Now Where Are They Now? The Cast Of Jerry Maguire


Perhaps just as outspoken as Laurel, was Rod’s wife, Marcee Tidwell. Similarly, Marcee upheld the role of the concerned spouse. Even with a relatively minor role in the film, King’s character asserted herself as a strong female presence who acted as the foundation of her family, and the solid rock on which Rod depended. Their marriage was, at times, a complete foil to Dorothy and Jerry’s relationship. As an example of what a loving, devoted partnership looked like, Jerry was forced to evaluate his own relationship throughout the film’s narrative.

Regina King has been active in many different facets of Hollywood. Recently, she has been thriving as a recurring character on multiple, successful television series: The Leftovers, The Big Bang Theory, and Southland just to name a few. King has even displayed her voice acting chops by voicing brothers Huey and Riley Freeman on the hit animated, adult comedy, The Boondocks. Most notably in the realm of film, Regina King has lent her acting talents to the Academy Award winning biopic, Ray, and the Will Smith, Gene Hackman led 1998 crime drama, Enemy of the State. Currently, the Los Angeles born actress is starring as Terri LaCroix on ABC’s hit television drama, American Crime.

2. Renée Zellweger (Dorothy Boyd)

Rene  e Zellweger Then and Now Where Are They Now? The Cast Of Jerry Maguire


Dorothy Boyd portrayed the level-headed, yet at times impulsive love interest to the titular Jerry Maguire. When Jerry decided that he is going to start his own sports management firm, Dorothy impetuously agrees to join Maguire without really knowing him all too well, and with little regard to her financial well-being along with best interest of her young son Ray. She was a woman that (up until Jerry entered the picture) always took the sensible path and generally chose to be responsible well beyond her years.

Between the years of 2001 and 2004, there was arguably no actress hotter in Hollywood than Renée Zellweger. In three consecutive years, Zellweger was nominated for Best Actress – twice in a leading role, once as a supporting actress – and finally took home the gold statue for her portrayal of Ruby Thewes in Anthony Minghella’s directorial effort, Cold Mountain. The Oscar winning actress has been on a bit of a hiatus from film over the past six years or so, but it appears as though a comeback is in the works, with two motion pictures slated for release in 2016 – director Courtney Hunt’s sophomore effort entitled, The Whole Truth, and the latest installment of the Bridget Jones series, Bridget Jones’s Baby.

1. Cuba Gooding Jr. (Rod Tidwell)

Cuba Gooding Jr. Then and Now Where Are They Now? The Cast Of Jerry Maguire


Rod Tidwell is arguably the most memorable character from the entire film. Decades later, we still recall his famous catchphrase “show me the money,” his elaborate touchdown dances, and of course, his loyalty to Jerry. Rod acted as the comic relief for much of this film, and still, he served to add emotional depth as well. The character was so lovable, eccentric, and not to mention well-acted, that Cuba Gooding Jr. won an Academy Award for Best Actor in a Supporting Role.

Sure, Cuba Gooding Jr. has been involved in some of Hollywood’s more teased movies, receiving Razzie nominations for multiple films with in the same year – Daddy Day Camp and Norbit for 2008’s award show, and Boat Trip, Radio, and The Fighting Temptations in 2004. Still, Gooding Jr. has been in a number of quality films over the past 20 years – Selma, American Gangster, and As Good as it Gets. Maybe his career has not been quite as promising as one would have speculated walking out of Jerry Maguire in 1996, but hopefully we are seeing a bit of a resurgence, as Gooding Jr. recently starred as O.J. Simpson in the critically acclaimed drama American Crime Story.

Can you believe it has already been 20 years already? Who are some of your favorite character’s and actors from this former Best Picture nominee? Make sure to let us hear it in the comments section.