Lopez played dedicated but unlucky in love wedding planner Mary Fiore, marking her second major film role following her breakout in 1997’s Selena. In his tough review of the film, critic Robert Ebert wrote, “A plot like this is so hopeless that only acting can redeem it. Lopez pulls her share of the load, looking genuinely smitten.”
Since the movie hit theaters, Lopez has pretty much been everywhere. Shortly after The Wedding Planner came Enough and Maid in Manhattan and a handful of more films; she continued to release hit music including, shortly after the film, “Jenny from the Block”; she wrapped a successful Las Vegas residency; she joined the judges’ panel on American Idol; she had twins with now-ex-husband Marc Anthony; she got engaged to Alex Rodriguez; and most recently performed at both the Super Bowl LIV halftime show and the 2021 presidential inauguration.
McConaughey was a major leading man when he took on the role of groom Dr. Steve “Eddie” Edison, who rescued and ultimately fell in love with Mary. Though beloved by fans of the film, he actually ranked it last of his trio of early 2000s romantic comedies when speaking to Andy Cohen on a 2019 episode of Watch What Happens Live. (How to Lose a Guy in 10 Days was first, Failure to Launch second.)
Years later he’d transform himself for roles in Magic Mike, The Wolf of Wall Street and Dallas Buyers Club, for which he won an Oscar. The actor — who just released a book, Greenlights — is married to Camila Alves, with whom he has three young children.
The quintessential best friend and coworker, Greer’s Penny attempted to keep Mary on the straight and narrow despite her feelings for Eddie.
The Wedding Planner was one of Greer’s first major roles, leading her to best friend parts in movies like 13 Going on 30 and 27 Dresses. She most recently appeared on Kidding, though lends her voices to characters on every show from Archer to Let’s Go Luna! She is married to producer Dean E. Johnsen.
Wilson-Sampras — a former Miss Teen USA — played well-to-do bride-to-be Fran Donolly, who ultimately realized she wasn’t in love with Eddie, leaving him free to fall for Mary.
Following The Wedding Planner, Wilson-Sampras slowly retreated from the spotlight; her last on-screen credit is from a 2008 film. She is married to tennis star Pete Sampras, with whom she has two sons.
Before he hit it big on Grey’s Anatomy, Chambers, a former model, was the sweetly love-struck Massimo, who came seconds from marrying Mary at the behest of her father.
Four years after the film, Chambers hit it big as Dr. Alex Karev on Grey’s Anatomy, a role he just left last year. He and wife Keisha have five children together.
Kimbrough, a.k.a. Fran’s father, was well-known for his Emmy-winning role on Murphy Brown when The Wedding Planner came around.
He’s also known for voice work and Broadway roles and even came back for the Murphy Brown revival in 2018, though has largely stayed out of the spotlight. He was most recently married to late actress Beth Howland, and has one son.
Another very familiar face, TV and Broadway vet Gleason played Fran’s mother. By the time The Wedding Planner came out, she had roles on Friends and The West Wing under her belt, in addition to dozens of other credits.
In the years since, she’s stayed busy, most recently on The Affair and Sensitive Skin. She is married to actor Chris Sarandon and has one child from a previous marriage.
As Geri, Najimy was the boss Mary was trying to impress with her wedding plans for ill-fated pair Fran and Eddie. A household name when The Wedding Planner hit theaters, she’d already appeared in films like Hocus Pocus and Sister Act and on TV’s Pepper Ann and Veronica’s Closet.
She’s continued to work steadily since 2001, famously voicing Peggy Hill on King of the Hill in addition to other roles, and is heading back to the big screen for Hocus Pocus 2. She is married to singer/actor Dan Finnerty, with whom she has one daughter.
Rocco brought heart as Mary’s father Salvatore, who desperately wanted to see his daughter happily married. Prior to the movie, he had practically endless film credits including roles in The Godfather and The Famous Teddy Z.
The Emmy winner worked steadily until his death at age 79 in 2015; he was married to actress Shannon Wilcox, with whom he had two children.
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