Revisiting the Iconic Cast of 'You've Got Mail': Meg Ryan, Tom Hanks, Dave Chappelle and Beyond

AOL's instant messaging may be a thing of the past, but "You've Got Mail" has remained timeless.

This 1998 romantic comedy features Meg Ryan and Tom Hanks as competing bookstore owners. Ryan's character, Kathleen Kelly, owns The Shop Around the Corner, while Hanks' character, Joe Fox, founds the Fox Books chain, which threatens her business. Through online chat conversations as "Shopgirl" and "NY152," they unknowingly fall in love.

Hanks and Ryan, who previously starred in Joe Versus the Volcano and Sleepless in Seattle, reunited for You've Got Mail with hopes of achieving another successful box-office hit. Former Warner Bros. cochair Terry Semel expressed his anticipation, stating, "You never know if that magical chemistry will happen again, but the love story between these two individuals, particularly Tom and Meg, has universal appeal. They are the epitome of a perfect couple, like Mr. and Mrs. World."

Scroll down to see what the cast of the ’90s film is up to now — including stars Parker Posey, Dave Chappelle, Chris Messina and Greg Kinnear.

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‘You’ve Got Mail’ Cast: Where Are They Now? Meg Ryan, Tom Hanks, Dave Chappelle and More

AOL's instant messaging may be a thing of the past, but the timeless charm of You've Got Mail remains.

This romantic comedy from 1998 features Meg Ryan and Tom Hanks as rival bookstore owners. Ryan plays the role of Kathleen Kelly, who owns The Shop Around the Corner. Hanks portrays Joe Fox, the founder of the Fox Books chain that poses a threat to Kathleen's business. Through online chatting, the characters known as "Shopgirl" and "NY152" unknowingly develop a deep connection and fall in love.

Starring together in Joe Versus the Volcano and Sleepless in Seattle, Hanks and Ryan reunited for You've Got Mail, hoping for another successful box-office hit. Former Warner Bros. cochair Terry Semel expressed his excitement, stating that the chemistry between the two actors was magical and that their onscreen romance had international appeal. Semel even went as far as to compare Hanks and Ryan to a perfect couple, calling them "Mr. and Mrs. World."

Scroll down to see what the cast of the '90s film is up to now — including stars Parker Posey, Dave Chappelle, Chris Messina and Greg Kinnear.

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Meg Ryan

Ryan has had a successful career in acting, starring in various films such as Hanging Up, Proof of Life, Kate & Leopold, The Women, and Serious Moonlight. She has also appeared on the television show Web Therapy and both starred in and produced Picture Paris. In 2015, she made her directorial debut with Ithaca.

During her marriage to Dennis Quaid from 1991 to 2001, Ryan had a son named Jack. She is also the mother of daughter Daisy, whom she adopted in 2006. In 2011, Ryan began an on-again, off-again relationship with singer John Mellencamp. Although they announced their engagement, they ultimately called it quits in November 2019. However, there have been rumors of the pair rekindling their relationship, with confirmation in November 2022 that Mellencamp is now dating Marianelly Agosto.

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Tom Hanks

After his portrayal of Fox Books founder Joe Fox, Hanks went on to star in various acclaimed films such as Saving Private Ryan, The Green Mile, Cast Away, and Catch Me If You Can. He also brought life to the iconic character Woody in the Toy Story franchise and took on leading roles in The Da Vinci Code, Charlie Wilson’s War, Captain Phillips, Saving Mr. Banks, and Sully. Apart from his acting prowess, Hanks is also recognized for his talents as a writer, director, and producer. Some of his notable production credits include Band of Brothers, My Big Fat Greek Wedding (which he collaborated on with his wife Rita Wilson), Big Love, The Nineties, and A Man Called Ove.

The California native tied the knot with Wilson in 1988, and together they have two sons, Chet and Truman. Hanks is also the proud father of son Colin and daughter Elizabeth from his previous marriage. In 2017, Hanks released a compilation of short stories titled Uncommon Type, which drew inspiration from his experiences with his beloved typewriter.

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Parker Posey

Posey portrayed Patricia Eden, Joe's girlfriend, in the mentioned project. Following that, she went on to star in various works such as Josie and the Pussycats, The Sweetest Thing, Laws of Attraction, Café Society, The Architect, and Elsewhere. Hailing from Maryland, the actress also made appearances in a few episodes of Boston Legal before securing roles in Granite Flats, Skylanders Academy, and Lost in Space. Furthermore, Posey showcased her talent on Broadway in Taller Than a Dwarf and The Realistic Joneses. In 2018, she penned the captivating memoir You're on an Airplane: A Self-Mythologizing Memoir. The following year, Posey ventured into the world of scripted podcasts, starring in "Hunted," a production by Endeavor Audio and Dick Wolf's Wolf Entertainment.

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Greg Kinnear

Kinnear, a native of Indiana, played the role of Kathleen's boyfriend and writer for The New York Observer, Frank Navasky. He went on to appear in several films including Someone Like You, We Were Soldiers, Little Miss Sunshine, Invincible, The Last Song, Strange But True, and Misbehavior. Additionally, he made appearances in television shows such as The Kennedys, Rake, and House of Cards, earning an Oscar nomination.

Beyond his acting career, Kinnear has also ventured into producing and writing. He served as an executive producer and writer for Later, and took on the roles of both producer and director for Phil. In January 2022, he finally made his long-awaited Broadway debut in To Kill a Mockingbird after a two-year delay caused by the coronavirus pandemic.

Since 1999, Kinnear has been happily married to model Helen Labdon. The couple is blessed with three daughters.

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Steve Zahn

Zahn's acting career continued to flourish after his role as assistant George Pappas in Shop Around the Corner. He went on to star in a variety of films, including Saving Silverman, Riding in Cars With Boys, Daddy Day Care, Dallas Buyers Club, Where’d You Go Bernadette, and the Diary of a Wimpy Kid franchise. Additionally, he showcased his talent on television, portraying Davis McAlary on Treme, Clark Edwards on Mind Games, Jude Ellis on The Crossing, and voicing Dude on The Healing Powers of Dude.

Zahn married Robyn Peterman in 1994. The couple share two children. They also started a community theater in Kentucky, which Zahn occasionally stars in.

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Heather Burns

Burns portrayed bookstore worker Christina Plutzker in the movie. Since then, she has appeared in various films such as the Miss Congeniality series, Two Weeks Notice, Bewitched, Valley of the Sun, Manchester by the Sea, and Brave New Jersey. On the television front, the Chicago native has been credited with roles in Twenty Good Years, Bored to Death, Save Me, and Blindspot. Additionally, she has showcased her talent in off-Broadway productions including Middletown, Dinner With Friends, and Peace for Mary Frances. In 2012, Burns tied the knot with actor Ajay Naidu.

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Dave Chappelle

Kevin Jackson, a friend and coworker of Joe, was brilliantly portrayed by the comedian. Over the years, he has showcased his talent in popular movies like Half-Baked, Blue Streak, Undercover Brother, and A Star Is Born. From 2003 to 2006, he took the entertainment world by storm as the writer, producer, and host of his iconic series, Chappelle's Show. Additionally, he has been behind the creation and production of various television specials, such as Dave Chappelle: The Bird Revelation and Dave Chappelle: 8:46. The comedian's extraordinary abilities were recognized with a Grammy Award for Best Comedy Album in 2018.

The Washington D.C. native married his wife, Elaine, in 2001. The pair share two sons and a daughter.

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Dabney Coleman

Playing the role of Joe's dad, Nelson Fox, Coleman later went on to voice Principal Prickly in the Recess series and its subsequent films. hailing from Texas, he also had notable roles in Inspector Gadget, Where the Red Fern Grows, Domino, and Rules Don't Apply. Additionally, Coleman portrayed Burton Fallin in The Guardian, Dr. Bart Jacobs in Heartland, Commodore Louis Kaestner in Boardwalk Empire, and made guest appearances on Ray Donovan and NCIS. He is a father to four children, whom he shares with his second wife, Jean Hale.

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Jean Stapleton

Birdie Conrad, the character played by the Golden Globe winner, was a bookstore worker. In addition to this, Stapleton also lent her voice to the character of Mrs. Jenkins in Pocahontas 2: Journey to a New World. This year also marked her appearance in Chance of a Lifetime, which coincided with her role in You’ve Got Mail. Following these projects, the All in the Family alum went on to star in Baby, Pursuit of Happiness, and Like Mother Like Son: The Strange Story of Sante and Kenny Kimes before taking a break from acting in 2001. Her contributions to the industry led to her induction into both the American Theatre Hall of Fame and the Television Hall of Fame in 2002.

The New York native died in May 2013 at the age of 90. She is survived by her two children.

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Jeffrey Scaperrotta and Hallee Hirsh

Scaperrotta made his acting debut as Matt Fox, Joe's 4-year-old half-brother, in the same year he appeared in One True Thing. He later appeared in Hollow Man before landing the role of Dickie Stabler, Detective Elliott Stabler's son, on Law & Order: Special Victims Unit. His most recent onscreen appearances were in Spy (2011) and Fort Tilden (2014).

As for Hirsh, she played Annabelle Fox, Joe's 11-year-old aunt. The actress then starred in The Ultimate Christmas Present on Disney Channel, as well as Speak, Bad Behavior, and The Last Dinner Party. Hirsch also had recurring roles on JAG, Flight 29 Down, ER, and Sloppy Tacos. After taking a break from acting, she purchased Hole Doughnuts in Asheville, North Carolina. In 2013, she married Ryan Martin and describes herself as a "yurt-dweller" on Instagram. The couple has two children together.

The actors reunited in 2018 to talk about their childhood roles in You’ve Got Mail on the Today show.

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Chris Messina

In the film, Messina plays a Fox Books employee who confuses Ballet Shoes with Skating Shoes. After that, he appeared in various other films such as Made of Honor, Julie & Julia, An Invisible Sign, Argo, Cake, The Secrets We Keep, and Birds of Prey. Not only that, but he has also taken on TV roles in shows like Six Feet Under, Damages, The Newsroom, The Mindy Project (which paid homage to You’ve Got Mail in several episodes), Sharp Objects, and The Sinner.

Originally from New York, Messina was previously married to actress Rosemarie DeWitt from 1995 to 2006. Since 2007, he has been in a relationship with film producer Jennifer Todd, and they have two sons together.