The Wedding Planner: Celebrating 20 Years and Catching Up With the Iconic Cast

Two decades ago, a charming romantic comedy burst onto the scene, quickly becoming a staple in the hearts of fans worldwide. Released on January 26, 2001, The Wedding Planner offered a delightful blend of humor, romance, and unexpected twists, solidifying its place as one of the most beloved films of the early 2000s. Starring the undeniable talents of Jennifer Lopez and Matthew McConaughey, the movie captivated audiences with its enchanting storyline about a driven wedding planner who unexpectedly falls for the groom of one of her high-profile clients.

The on-screen chemistry between Jennifer Lopez, who embodied the meticulous Mary Fiore, and Matthew McConaughey, portraying the swoon-worthy Steve Edison, was electric, making their journey to love a truly memorable one. As we commemorate the 20th anniversary of this iconic film, it’s the perfect opportunity to reflect on its enduring legacy and catch up with the talented ensemble cast. From global music sensations and Oscar winners to television mainstays and acclaimed character actors, the stars of The Wedding Planner have carved out impressive careers and personal lives. Join us as we take a look at where the cast members are today and how their lives have transformed since they brought this romantic gem to life.

Jennifer Lopez: From Rom-Com Royalty to Global Superstar

Jennifer Lopez’s portrayal of Mary Fiore in The Wedding Planner was a landmark role, effectively launching her reign as a romantic comedy icon. This film marked the beginning of a highly successful period where J.Lo starred in a series of popular rom-coms, including fan favorites like Maid In Manhattan, Shall We Dance?, and Monster-In-Law. Her natural charm and captivating screen presence made her an instant box office draw. Beyond comedies, Jennifer has consistently sought out challenging roles, showcasing her versatile acting abilities. Her powerful performance in the 2019 crime drama Hustlers, where she played the fierce Ramona Vega, garnered widespread critical acclaim and earned her a Golden Globe nomination, proving her enduring talent and range.

Jennifer’s career achievements are not limited to film. She has also made a significant impact on television, notably serving as a judge on the immensely popular competition series American Idol for multiple seasons (10, 11, and 13 through 16), where she offered guidance and inspiration to aspiring singers. From 2016 to 2018, she took on a more dramatic role as the lead in the NBC police procedural Shades of Blue, further demonstrating her versatility. Her passion for dance led her to executive produce and judge four seasons of World of Dance, a platform where she celebrated incredible dance talent from across the globe. Alongside her thriving acting career, Jennifer has consistently released new music, cementing her status as a global pop star. She has released six studio albums since 2001, producing numerous hit singles and undertaking successful world tours. Her unforgettable co-headlining performance at the 2020 Super Bowl halftime show with Shakira was a spectacular display of showmanship and cultural significance. More recently, she delivered a poignant and powerful performance at the inauguration of President Joe Biden, underscoring her continued relevance and influence across entertainment and public life.

Jennifer’s personal life has been as dynamic and newsworthy as her career. At the time of The Wedding Planner’s release, she was married to Cris Judd, though their marriage concluded in June 2002. She then began a high-profile relationship with actor Ben Affleck, leading to an engagement in November 2002. The couple, affectionately known as “Bennifer,” became a media sensation, but their planned September 2003 wedding was postponed, and they ultimately split in 2004. Later that year, Jennifer married Latin music superstar Marc Anthony. In 2008, they welcomed their beloved twins, EmmeandMax. After a decade together, J.Lo and Marc finalized their divorce in 2014, maintaining a friendly co-parenting relationship. She subsequently dated Casper Smart on and off from 2011 to 2016. In 2017, Jennifer began a much-talked-about relationship with former New York Yankees star Alex Rodriguez, which culminated in their engagement in March 2019. Her journey through love, motherhood, and career has made Jennifer Lopez a truly multifaceted and inspiring global icon.

Matthew McConaughey: From Rom-Com Heartthrob to Academy Award Winner

In The Wedding Planner, Matthew McConaughey captivated audiences as the charismatic and dreamy pediatrician Steve Edison, the unsuspecting groom who finds himself falling for his wedding planner. By 2001, Matthew had already established himself as a prominent actor with roles in films like Dazed and Confused and Contact. His performance in The Wedding Planner further solidified his reputation as a leading man, particularly in romantic comedies, a genre he would frequent in the early 2000s with hits like How To Lose A Guy in 10 Days and the adventure film Sahara, charming audiences with his distinctive allure.

The 2010s marked a remarkable shift in Matthew’s career, famously dubbed the “McConaissance.” He consciously transitioned away from romantic comedies to embrace more challenging and complex dramatic roles, revealing an incredible depth and range that earned him widespread critical acclaim. This transformative period saw him star in a series of critically lauded films, including the legal thriller The Lincoln Lawyer, the male stripper dramedy Magic Mike, and the acclaimed independent film Mud. His scene-stealing role in Martin Scorsese’s The Wolf of Wall Street further showcased his powerful screen presence. The pinnacle of this career evolution came in 2013 with his mesmerizing portrayal of Ron Woodroof, a real-life AIDS patient, in Dallas Buyers Club, for which he received his first Academy Award for Best Actor. He continued to impress with his leading role in Christopher Nolan’s epic science fiction film Interstellar, proving his ability to anchor major blockbusters with profound emotional weight and intellectual gravitas.

Matthew also conquered the small screen with an unforgettable performance as the brooding detective Rust Cohle in the inaugural season of HBO’s critically acclaimed series True Detective. His intense and philosophical portrayal earned him Emmy and Golden Globe nominations, cementing his status as one of the most compelling actors of his generation. More recently, he starred in Guy Ritchie’s 2019 crime-comedy The Gentlemen and is set to reprise his popular voice role as Buster Moon in the upcoming Sing sequel. Beyond his acting prowess, Matthew is also a successful author, having published his candid and reflective memoir, Greenlights, in 2020. The book became an instant bestseller, offering a unique glimpse into his life philosophy and experiences. In his personal life, the actor found lasting love with Brazilian model Camila Alves. They got engaged in 2011, married in 2012, and are devoted parents to three children, building a strong family foundation that he often speaks about with great affection and pride.

Justin Chambers: From Rom-Com Charmer to Grey’s Anatomy Stalwart

Justin Chambers brought warmth and humor to his role as Massimo Lenzetti, Mary’s adorable and persistent childhood friend who harbored a long-standing crush, in The Wedding Planner. His portrayal of the good-natured Italian restaurateur, though ultimately not Mary’s happily ever after, left a memorable impression on audiences. While this film provided a charming early role, Justin’s career would truly take off a few years later with a groundbreaking part that would define a significant portion of his career: Dr. Alex Karev in Shonda Rhimes’ acclaimed medical drama, Grey’s Anatomy.

For an incredible 16 seasons, Justin was an integral part of the sprawling ensemble cast of Grey’s Anatomy. His character, Alex Karev, underwent one of the most profound transformations on the show, evolving from a brash, arrogant intern into a compassionate and skilled pediatric surgeon who became a beloved fan favorite. His journey through professional growth, personal struggles, and enduring friendships resonated deeply with millions of viewers worldwide. Fans were met with surprise when the actor announced his departure from Grey’s Anatomy in January 2020, with his final on-screen appearance having aired in November 2019. The show orchestrated an emotional farewell for Alex’s character in March 2020, revealing that he had reunited with his former love, Izzie Stevens, after discovering she had given birth to their twins. This poignant storyline provided a sense of closure for his character, though it sparked considerable discussion among the show’s dedicated fanbase. In his personal life, Justin has maintained a remarkably stable and private family life, marrying his wife, Keisha, in 1993. Together, they are proud parents to five children, demonstrating his commitment to his family away from the public eye.

Judy Greer: The Quintessential Best Friend and Versatile Talent

Judy Greer delivered a memorable performance as Penny Nicholson, Mary’s sharp-witted and supportive colleague and best friend, in The Wedding Planner. Over the past two decades, Judy has cultivated an incredibly prolific and diverse career, becoming one of Hollywood’s most recognizable and beloved character actresses. Known for her impeccable comedic timing and ability to bring depth to often secondary roles, she consistently steals scenes and leaves a lasting impression.

Her extensive filmography spans various genres, including popular romantic comedies like 13 Going on 30 and 27 Dresses, where she often played the relatable and endearing best friend. Judy has also showcased her dramatic abilities in films such as M. Night Shyamalan’s psychological thriller The Village and the critically acclaimed family drama The Descendants, demonstrating her remarkable range. In recent years, she has become a fixture in major blockbuster franchises, appearing in the successful rebooted Planet of the Apes series (e.g., War for the Planet of the Apes) and as Maggie Lang, the ex-wife of Ant-Man, in Marvel’s Ant-Man and its sequel, Ant-Man and the Wasp. Venturing into the horror genre, she earned praise for her role in the highly anticipated 2018 Halloween sequel and is set to reprise her character in the upcoming 2021 sequel,Halloween Kills, further cementing her versatile presence in Hollywood.

On television, Judy has also left an indelible mark, particularly through her distinctive voice work. She is widely recognized for voicing the eccentric and hilarious Cheryl Tunt (or Carol) in the popular FXX animated spy comedy series Archer, a role that has earned her a dedicated fanbase. Her live-action television appearances include memorable guest spots in iconic sitcoms like Arrested Development and Two and a Half Men. More recently, she starred alongside Jim Carrey in the critically acclaimed Showtime dramedy Kidding, where she once again demonstrated her capacity for nuanced and emotionally complex performances. Judy Greer remains a celebrated and consistently entertaining actress, effortlessly transitioning between comedic and dramatic roles, always bringing a unique spark to every character she embodies.

Kathy Najimy: From Beloved Comedian to Hocus Pocus Reunion

In The Wedding Planner, veteran actress Kathy Najimy brought her distinctive comedic timing and warm presence to the role of Geri, Mary’s supportive and insightful boss. Kathy’s career has been marked by her ability to infuse characters with genuine humor and heart, making her a beloved figure in both live-action and voice roles. Following her appearance in The Wedding Planner, she continued to expand her diverse filmography with roles in films like the star-studded ensemble comedy Rat Race, Pixar’s critically acclaimed animated feature WALL-E (as the voice of Mary), and Tyler Perry’s holiday film A Madea Christmas.

One of Kathy’s most iconic and long-lasting roles is her voice work as Peggy Hill on the beloved animated series King of the Hill. For over a decade, from 1997 to 2010, her distinctive voice brought to life the confident, albeit often misguided, substitute teacher, earning her widespread recognition and a cherished place in animation history. Over the years, Kathy has also made numerous guest appearances on various television shows, showcasing her versatility across genres. These roles include memorable turns in critically acclaimed political satire like Veep, popular millennial comedies like Younger, and the animated series Duncanville, where she continues to lend her unique vocal talents. Her consistent work across different platforms highlights her enduring appeal and adaptability in the entertainment industry.

Currently, there’s immense excitement surrounding the impending Hocus Pocussequel, which is highly anticipated by fans of the Halloween classic. Kathy is widely expected to reprise her iconic role as the vacuum-riding witch Mary Sanderson, much to the delight of audiences who grew up with the original film. Sharing a glimpse into the development, Kathy revealed in a January 2021 interview on SiriusXM’sThe Jess Cagle Show, “Sarah [Jessica Parker] and Bette [Midler] and I had like a couple of weeks on the phone talking about the script, and that was really fun, obviously,” teasing the highly anticipated reunion of the Sanderson sisters. This continued involvement in beloved projects underscores her lasting impact and strong connection with her fanbase.

Bridgette Wilson: From Rom-Com Obstacle to Dedicated Family Life

Bridgette Wilson portrayed Fran Donelly, Steve’s beautiful but ultimately incompatible fiancée, in the hit 2001 romantic comedy. Fran served as the primary romantic obstacle for Mary and Steve, making Bridgette’s portrayal crucial to the film’s central conflict and eventual resolution. Prior to The Wedding Planner, Bridgette had already gained significant recognition for her roles in films such as Billy Madison, where she played the memorable love interest Veronica Vaughn, and the popular video game adaptation Mortal Kombat. She was a notable presence in 90s cinema, often embodying charming and impactful characters.

After her role in The Wedding Planner, Bridgette continued her acting career for several years, appearing in a diverse range of films. These included the Steve Martin romantic comedy Shopgirl, the independent film Buying the Cow, and her latest film credit, the 2008 movie Phantom Punch. On the television front, she made notable guest appearances in popular shows during the early 2000s, including a memorable turn in the iconic sitcom Frasier, as well as roles in crime dramas like CSI: Miami and the comedy series Jake in Progress. However, in the mid-2000s, Bridgette gradually transitioned away from the demands of a full-time acting career to focus more on her personal life and family. She married legendary tennis player Pete Sampras in 2000, and together they have two sons, Christian Charles and Ryan Nikolaos. Her decision to prioritize her family has led to fewer public appearances and acting projects, allowing her to enjoy a more private life away from the constant spotlight of Hollywood. Despite her reduced presence in the entertainment world, her roles in films like The Wedding Planner remain fondly remembered by fans of romantic comedies and 90s cinema.