By Jessica Wedemeyer
9:41pm PDT, Jul 30, 2025
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Julia Roberts starred as "two-faced, big-haired food critic" Julianne Potter, who made a pact with her best friend when they were in college that if neither of them were married by the time they turned 28, they'd marry each other.
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Julia Roberts scored her third Golden Globe nomination for her work in "My Best Friend's Wedding" — she'd previously won for "Steel Magnolias" and "Pretty Woman." She's earned many more nominations since then. In 2001, she won her third Globe — as well as her first Oscar — for her performance in "Erin Brockovich." Julia scored her fourth Academy Award nomination in 2014 for "August: Osage County." She also earned Emmy nominations in 1999 for her work on "Law & Order" and in 2014 for her performance on the HBO TV movie "The Normal Heart." More recently, she's found major success on the small screen with starring roles in the 2018 psychological-thriller series "Homecoming" and in the 2022 political-thriller series "Gaslit." Julia's famously active love life calmed after she starred in "My Best Friend's Wedding." In 2001, she and Benjamin Bratt split after nearly four years together. The next year, she married cameraman-turned-cinematographer Danny Moder. They now have three children: son Henry and twins Phinnaeus and Hazel.
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Dermot Mulroney starred as Julianne's best friend, Michael O'Neal.
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Dermot Mulroney stuck to the rom-com genre in the years following 1997's "My Best Friend's Wedding," starring in "The Wedding Date," "Must Love Dogs" and "The Family Stone." He's appeared in several high-profile dramas since then including "Zodiac," "J. Edgar" and "Jobs" and reunited with
Julia Roberts in 2013's acclaimed "August: Osage County." (He also worked with Julia again five years later on the psychological thriller series "Homecoming" in 2018.) He's also had stints on "Friends," "Enlightened," "New Girl," "Shameless" and "Mozart in the Jungle" and has popped up on "Station 19," "Arrested Development," "The Purge" and Mindy Kaling's 2019 "Four Weddings and a Funeral" reboot series.
Dermot is an accomplished cellist who's played on the scores of several major movie projects including "Mission: Impossible III" and "Star Trek Into Darkness." In 2007, he and Catherine Keener divorced after 17 years of marriage. They had one son together, Clyde. In 2010, he wed Prima Apollinaare, with whom he shares daughters Mabel Ray and Sally. He
filed for divorce in June 2025.
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Cameron Diaz starred as Michael's fiancée, Kimmy Wallace, a college girl from a wealthy family.
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In the years after she starred in "My Best Friend's Wedding,"
Cameron Diaz earned four Golden Globe nominations for her work in "There's Something About Mary," "Being John Malkovich," "Vanilla Sky" and "Gangs of New York." She also starred in "Any Given Sunday," "Charlie's Angels," "The Holiday," "The Green Hornet," "Bad Teacher," "The Other Woman" and "Sex Tape" and voiced Princess Fiona in the "Shrek" franchise. Cameron then took a decade-long
break from acting, returning to star in 2025's "Back in Action," her first gig since the 2014 remake of "Annie." During that time, she worked in other fields, authoring "The Body Book" in 2013 and "The Longevity Book" in 2016, and in 2020 launched Avaline, a line of organic wine. A year after "My Best Friend's Wedding" debuted, she and Matt Dillon parted ways after three years together. She went on to have high-profile relationships with Jared Leto, Justin Timberlake and Alex Rodriguez and was linked to John Mayer, Bradley Cooper, Diddy, Edward Norton and model Paul Sculfor before finding love with rocker Benji Madden. They tied the knot in 2015 and have since welcomed two children.
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Rupert Everett starred as Julianne's gay friend and editor, George Downes. Julianne pretends they're engaged.
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Rupert Everett scored his first Golden Globe nomination for his performance in "My Best Friend's Wedding." Two years later, he earned his second for his work in "An Ideal Husband." He's also starred in "A Midsummer Night's Dream," "Inspector Gadget," "The Importance of Being Earnest," "Stage Beauty," "Stardust" and "Miss Peregrine's Home for Peculiar Children" and voiced Prince Charming in the "Shrek" franchise. In 2018, the English star — who's appeared predominantly in stage productions in London, in independent films and on British TV projects — made his directorial debut with the Oscar Wilde biopic "The Happy Prince," which he also wrote and starred in. The openly gay actor, who's written novels and two memoirs, revealed in mid-2024 that he'd married his long-term partner, a Brazilian accountant named Henrique.
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Christopher Masterson portrayed Scotty O'Neal, Michael's younger brother and best man.
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Chris Masterson went on to star as Francis on "Malcolm in the Middle" from 2000 to 2006. He also appeared in "American History X" and "Scary Movie 2," starred on MTV's 2003 adaption of "Wuthering Heights," had brief stints on "That '70s Show" (his brother, Danny Masterson, played Hyde on the series) and "Haven" and voiced a character on "The Wild Thornberrys." Chris romanced Laura Prepon for nearly a decade until the mid-aughts and married actress Yolanda Pecoraro in 2019. They welcomed their first child together, a daughter, in 2021. The Scientologist also DJs under the name Chris Kennedy.
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Rachel Griffiths and Carrie Preston portrayed Kimmy's bridesmaids, twins Samantha and Mandy Newhouse.
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Rachel Griffiths scored an Oscar nomination in 1999 for her performance in "Hilary and Jackie." She went on to star on "Six Feet Under," for which she earned two Emmy nominations and two Golden Globe nominations, from 2001 to 2005. (She won the Globe in 2002.) She also starred on "Brothers and Sisters" from 2006 to 2011 and earned two more Emmy nominations as well as two more Golden Globe nominations for her work on the show. Additionally, she's appeared in "Blow," "The Rookie," "Ned Kelly," "Step Up," "Saving Mr. Banks" and "Hacksaw Ridge." The Australian actress wed artist Andrew Taylor in 2002; they have three children: daughters Adelaide Rose and Clementine Grace and son Banjo Patrick.
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Carrie Preston went on to appear in "Mercury Rising," "Cradle Will Rock," "The Legend of Bagger Vance," the 2004 remake of "The Stepford Wives," "Transamerica," "Vicky Cristina Barcelona," "Doubt" and "Duplicity." But it wasn't until she was cast as Arlene Fowler on "True Blood" — where she remained from 2008 to 2014 — that she made her major breakthrough. She then had stints on "The Following," "Happyish," "Crowded," "Person of Interest" and "The Good Wife," for which she won an Emmy in 2013 and scored a second nomination in 2016. Carrie returned to the role of Elsbeth Tascioni on "The Good Fight" in 2017 and reunited with "My Best Friend's Wedding" co-star Rachel Griffiths on the 2017 ABC miniseries "When We Rise." From 2017 to 2022, she starred on the TNT comedy "Claws." She's been married to "Lost" star Michael Emerson since 1998.
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Susan Sullivan and Philip Bosco portrayed Kimmy's parents, Isabelle and Walter Wallace.
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Susan Sullivan went on to star on "Dharma & Greg," for which she earned a Golden Globe nomination, from 1997 to 2002. She then had stints on "The Drew Carey Show," "Judging Amy," "Hope and Faith" and "The Nine" before winning the part of Martha Rodgers on "Castle," on which she starred from 2009 to 2016. The former soap star and Playboy Bunny later popped up on "The Real O'Neals," "The Kominsky Method" and "Last Man Standing." She and author-psychologist Connell Cowan have been together since 1988.
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Philip Bosco went on to appear in "Shaft," "Kate & Leopold," "Hitch," "Freedomland" and "The Savages." He also had stints on "Law & Order," "Ed," "Law & Order: Special Victims Unit" and "Damages." The Broadway star and Tony winner passed away in 2018 from complications of dementia. He was 88. He is survived by his wife of 60 years, Nancy Ann Dunkle, with whom he reportedly shared seven children.
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M. Emmet Walsh portrayed Joe O'Neal, Michael's dad.
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M. Emmet Walsh — whose biggest hits, like "Midnight Cowboy," "Blade Runner" and "Blood Simple" came before "My Best Friend's Wedding," went on to appear in 1998's "Twilight," "Wild Wild West," "Snow Dogs," "Christmas with the Kranks," "Racing Stripes," "The Odd Life of Timothy Green" and "Calvary." He also had stints on "Damages" and "Sneaky Pete" and has voiced characters in "Pound Puppies" and "Adventure Time" as well as "The Iron Giant." He died at 88 in March 2024.
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