Tom Hanks as Joe Fox
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After this movie, we never heard from Tom Hanks again. Kidding! The actor continues to be both prolific and beloved since playing Joe Fox, the easygoing book superstore mogul. Following the film's release, Hanks earned three more Oscar nominations for his roles in Saving Private Ryan (1998), Cast Away (2000) and A Beautiful Day in the Neighborhood (2019).
Hanks has also won seven career Emmys and five Golden Globes so far, including being honored with the Cecil B. DeMille lifetime achievement award in 2020. He was a Kennedy Center honoree in 2014 and received a Presidential Medal of Freedom in 2016. Hanks paid tribute to You've Got Mail director Nora Ephron, who passed away in 2012, when he made his Broadway debut in her play Lucky Guy in 2013, receiving a Tony Award nomination for his performance.
In addition to the Toy Story movie franchise, the star's other notable film credits include The Green Mile (1999), Catch Me If You Can (2002), The Polar Express (2004), The Da Vinci Code (2005), Charlie Wilson's War (2007), Angels & Demons (2009), Larry Crowne (2011), Captain Philips (2013), Sully (2016), The Post (2017), Greyhound (2020), Elvis (2022), Pinocchio (2022) and A Man Called Otto (2022). The decorated actor even published the book Uncommon Type in 2017, inspired by his love of typewriters.
Hanks has been married to actress Rita Wilson since 1988, whom he first met on ABC's Bosom Buddies in 1981. Their blended family includes four adult children — Colin, Elizabeth, Chet and Truman.
Meg Ryan as Kathleen Kelly
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Meg Ryan's performance as children's bookstore owner Kathleen Kelly whose shop is threatened by Joe's Fox Books megachain earned the actress a Golden Globe nomination in 1999.
After You've Got Mail and 2001's Kate & Leopold, Ryan stepped away from romantic comedies. Instead, she turned to more serious fare with 2003's In the Cut and 2004's Against the Ropes before focusing on her work behind the camera as a director in 2015's Ithaca, which she and Hanks also starred. In 2022, she announced her return to the rom-com genre, directing and starring in the upcoming What Happens Later alongside The X-Files star David Duchovny.
Since You've Got Mail, Ryan finalized her divorce from actor Dennis Quaid in 2001. They share one child, actor Jack Quaid. She welcomed her daughter Daisy True through adoption in 2006. Ryan was also in a high-profile relationship with rock musician John Mellencamp, but they called off their engagement in November 2019.
Parker Posey as Patricia Eden
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Parker Posey played the uptight book editor girlfriend of Hanks' character (for whom she was so wrong!).
She continues to steadily act in movies — a favorite of director Christopher Guest, who cast her in his comedies Best in Show (2000), A Mighty Wind (2003), For Your Consideration (2006) and Mascots (2016) — and on TV, with roles on Parks and Recreation, The Good Wife, Louie, Granite Flats and Search Party.
Posey's mainstream film roles include Scream 3 (2000), The Sweetest Thing (2002), Blade: Trinity (2004) and Superman Returns (2006) and Elsewhere (2019). She also appeared on all three seasons of Netflix's Lost in Space and the HBO Max limited series The Staircase in 2022.
In 2009, Playwrights Horizon revealed that Posey was diagnosed with Lyme disease. She published the book You're on an Airplane: A Self-Mythologizing Memoir in 2018.
Greg Kinnear as Frank Navasky
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Greg Kinnear played Frank Navasky, the anxious newspaper columnist boyfriend of Ryan's character (for whom he was so wrong!).
After You've Got Mail, the Oscar-nominated actor starred in Mystery Men (1999), Nurse Betty (2000), We Were Soldiers (2002), Little Miss Sunshine (2006), Baby Mama (2008), Anchorman 2: The Legend Continues (2013) and Confirmation (2016) as then-Senator Joe Biden. His performances on The Kennedys and Modern Family earned him back-to-back Emmy nominations in 2011 and 2012. Kinnear's other notable TV credits include Rake, House of Cards, The Stand, Shining Vale, Black Bird and You. In 2022, he made his Broadway debut playing Atticus Finch in To Kill a Mockingbird.
Kinnear married model Helen Labdon in 1999, with whom he shares three daughters.
Steve Zahn as George Pappas
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Having previously shared the screen with Hanks in 1996's That Thing You Do!, Steve Zahn played Kathleen's shaggy-haired coworker, George Pappas, at The Shop Around the Corner.
Zahn has appeared in a variety of films following You've Got Mail, including Joy Ride (2001), Daddy Day Care (2003), Sahara (2005), Rescue Dawn (2006), A Perfect Getaway (2009) and the Diary of a Wimpy Kid film series. He received critical acclaim for his performances in 2013's Dallas Buyers Club and 2017's War for the Planet of the Apes.
The actor was also a series regular on Treme, Mind Games, Mad Dogs and The Crossing, in addition to the National Geographic docuseries Valley of the Boom and SHOWTIME's George & Tammy. In 2022, he earned an Emmy nomination for his role as Mark Mossbacher on HBO's The White Lotus. Zahn can also be seen in the 2023 films Your Place or Mine — starring Reese Witherspoon and Ashton Kutcher — and Gringa featuring Roselyn Sanchez and Judy Greer.
Zahn married actress and author Robyn Peterman in 1994, with whom he shares two kids.
Dave Chappelle as Kevin Jackson
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Yep, Dave Chappelle is in the movie, too, playing Joe's wisecracking best friend, Kevin Jackson.
Chappelle went on to have a blockbuster comedy career (including three years filming the megahit Chappelle's Show). After taking a break from the limelight, Chappelle returned to acting and releasing popular and controversial Netflix specials, which earned him three Emmys. Chappelle also appeared in 2015's Chi-Raq and in the 2018 rendition of A Star Is Born. He won two additional Emmys for his hosting stint on Saturday Night Live in 2017 and 2021. Chappelle has also won four Grammys for best comedy album throughout his career.
The What's in a Name? (2022) funnyman lives with his wife, Elaine Chappelle, and three kids on a farm in Ohio.
Heather Burns as Christina Plutzker
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You've Got Mail was Heather Burns' first major film. She played Christina Plutzker, a staffer at The Shop Around the Corner bookstore, a role she and Ryan prepped for by working for a week at an actual N.Y.C. children's bookstore.
Burns has been steadily working since the film's release, notably portraying Miss Rhode Island in Miss Congeniality (2000) and the sequel Miss Congeniality 2: Armed and Fabulous (2005). The actress reunited with Ephron for Bewitched (2005) and appeared in Manchester by the Sea (2016). Burns has also had recurring roles on The $treet, Twenty Good Years, Bored to Death, Save Me and Blindspot. In 2022, she guest starred on the HBO Max series Julia.
She has been married to Office Space actor Ajay Naidu since 2012, and they have one child together.
Jeffrey Scaperrotta and Hallee Hirsh as Matt and Annabelle Fox
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Jeffrey Scaperrotta and Halle Hirsh memorably played Joe's younger half-brother, Matt Fox, and young aunt, Annabelle Fox, respectively. The pair also reunited on the Today show in 2018 for the film's 20th anniversary to discuss their memories of working with Hanks and Ryan.
The two child actors have continued to act following the film's release, with Scaperrotta appearing in the 2000 film Hollow Man and having recurring roles on Law & Order: SVU and Law & Order: Organized Crime as Elliot Stabler's son, Dickie. Hirsh has starred in several independent films and appeared on JAG, Flight 29 Down and ER.
Dabney Coleman as Nelson Fox
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Emmy-winning actor Dabney Coleman had been working for over 30 years in Hollywood, starring in the 1980 film 9 to 5 before he was cast as Hanks' father, Nelson Fox, in You've Got Mail.
Following the film's 1998 release, Coleman appeared in Stuart Little (1999), Where the Red Fern Grows (2003), Domino (2005) and Rules Don't Apply (2016). His major TV credits include recurring roles on The Guardian, Courting Alex and Boardwalk Empire. Coleman was also a guest star on Ray Donovan, NCIS and Yellowstone in 2019, playing John Dutton Sr. He also voiced Principal Prickly on Disney's Recess and its subsequent animated films.
Coleman is twice-divorced and has four children.