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‘The Wedding Planner’ Cast Then & Now: See Jennifer Lopez & More 20 Years Later

‘The Wedding Planner’ is officially 20 years old. Even after two decades, J.Lo and Matthew McConaughey’s rom-com remains a fan-favorite. In honor of the 20th anniversary, take a look at the cast then and now.

The Wedding Planner is one of those early 2000s romantic comedies that holds a very special place in the hearts of fans. Everyone rooted for Jennifer Lopez, 51, to get the man of her dreams in the film that was released on Jan. 26, 2001. Jennifer’s character, Mary, ends up falling for the groom of the wedding she’s planning. Cue the ultimate rom-com scenario.

The movie starred another rom-com favorite, the swoonworthy Matthew McConaughey, 51. J.Lo and Matthew’s chemistry was off the charts, and their characters get their happily ever after in the end. In the 20 years since The Wedding Planner was released, Jennifer and Matthew have become two of Hollywood’s biggest stars. Take a look at how the cast has changed and see what they’re up to now.

Jennifer Lopez Then & Now

Jennifer Lopez
Jennifer Lopez played Mary Fiore. (The Everett Collection/AP)

Jennifer Lopez’s role as Mary Fiore in The Wedding Planner was the first of J.Lo’s rom-com reign. After The Wedding Planner, Jennifer’s career really took off. She went on to star in hit films like Maid In Manhattan, Shall We Dance?, Monster-In-Law, and more. She earned rave reviews for her role in the 2019 film Hustlers. Jennifer earned a Golden Globe nomination for her performance.

J.Lo has also had a major presence on television. She was a judge on American Idol for seasons 10 and 11, as well as seasons 13 to 16. She starred in the NBC drama Shades of Blue from 2016 to 2018. Jennifer has also been one of the judges on World of Dance for 4 seasons and serves as an executive producer. In addition to becoming a bonafide movie and television star, Jennifer has continued to release new music. She has released 6 studio albums since 2001. She notably co-headlined the 2020 Super Bowl with Shakira, 43, and recently performed at the inauguration for President Joe Biden, 78.

At the time The Wedding Planner was released, Jennifer was married to Cris Judd, 51. They split in June 2002. Jennifer began dating Ben Affleck, 48, and they got engaged in Nov. 2002. Bennifer intended to get married in Sept. 2003, but they postponed their nuptials. They split in 2004. Jennifer married Marc Anthony, 52, that same year. They welcomed twins, Emme and Max, in 2008. J.Lo and Marc’s divorce was finalized in 2014. She dated Casper Smart, 33, on and off from 2011 to 2016. She began dating Alex Rodriguez, 45, in 2017. They announced their engagement in March 2019.

Matthew McConaughey Then & Now

Matthew McConaughey
Matthew McConaughey played Steve Edison. (The Everett Collection/AP)

Matthew McConaughey starred as the dreamy Steve Edison in The Wedding Planner. Matthew was already a major star in Hollywood when The Wedding Planner was released, and his rise continued. He starred in movies like How To Lose A Guy in 10 Days, Sahara, Tropic Thunder, The Lincoln Lawyer, Magic Mike, The Wolf of Wall Street, Interstellar, and more. He won his first Oscar for his role in the 2013 film Dallas Buyers Club.

His most recent roles include Mickey Pearson in the 2019 film The Gentlemen, and he’s set to reprise the voice role of Buster Moon in the Sing sequel. Matthew earned critical acclaim for his role as Rust Cohle in the first season of True Detective. His performance earned him Emmy and Golden Globe nominations.

The actor got engaged to Camila Alves, 38, in 2011. They married in 2012 and have three kids together. The Oscar winner published his memoir, Greenlights, in 2020.

Justin Chambers Then & Now

Justin Chambers
Justin Chambers played Massimo Lenzetti. (The Everett Collection/AP)

Justin Chambers, 50, starred as the adorable goofball Massimo Lenzetti in The Wedding Planner. His breakout role would come just a few years later with Grey’s Anatomy. He starred as Dr. Alex Karev in the long-running ABC series for 16 seasons. He shockingly left the series in the middle of season 16.

The actor announced his departure from Grey’s Anatomy in Jan. 2020. His final episode was in Nov. 2019. The show bid his character farewell in March 2020. Fans learned Alex had found out Izzie had given birth to their twins and he went to Kansas to be with her. In real life, Justin married his wife, Keisha, in 1993. They have 5 children together.

Judy Greer Then & Now

Judy Greer
Judy Greer starred as Penny Nicholson. (The Everett Collection/AP)

Judy Greer, 45, played Mary’s colleague and friend, Penny. Over the years, Judy has starred in films like 13 Going on 30, The Village, 27 Dresses, The Descendants, War for the Planet of the Apes, the Ant-Man movies, and more. She starred in the highly-anticipated Halloween sequel in 2018 and will reprise her role in the 2021 sequel.

Judy has also had a number of TV roles. She is widely recognized for voicing the role of Cheryl Tunt in the FXX series Archer. She’s appeared in other TV series like Arrested Development, Two and a Half Men, and Kidding.

Kathy Najimy Then & Now

Kathy Najimy
Kathy Najimy played Geri in the movie. (The Everett Collection/AP)

Kathy Najimy, 63, played Mary’s boss, Geri. Kathy went on to star in movies like Rat Race, WALL-E, A Madea Christmas, and more. She voiced the role of Peggy Hill on King of the Hill from 1997 to 2010. Kathy has guest-starred on a number of TV shows over the years, including Veep, Younger, and Duncanville.

A Hocus Pocus sequel in the works, with Kathy expected to reprise her role as Mary Sanderson. “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,” Kathy said on SiriusXM’s The Jess Cagle Show in Jan. 2021.

Bridgette Wilson Then & Now

Bridgette Wilson
Bridgette Wilson starred as Fran Donelly. (The Everett Collection/AP)

Bridgette Wilson, 47, played Steve’s fiancee, Fran, in the hit 2001 rom-com. Prior to The Wedding Planner, Bridgette had notably starred in Billy Madison. Bridgette’s films after The Wedding Planner include Shopgirl, Buying the Cow, and more. Her latest film role was the 2008 movie Phantom Punch. She also guest-starred in TV shows like Frasier, CSI: Miami, and Jake in Progress in the early 2000s.

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