In honor of the film's 20th anniversary, take a look at the careers of the cast of Nora Ephron's beloved romantic comedy.
In 1998, writer-director Nora Ephron reimagined romance in the internet age, bringing rival bookstore owners together online in You've Got Mail.
Twenty years later and the internet has changed quite a bit, but fans of the film still swoon over Tom Hanks and Meg Ryan's AOL-driven romance.
Ryan, who previously starred opposite Hanks in the Ephron-directed Sleepless in Seattle, plays Kathleen Kelly, the owner of a boutique bookshop that's threatened by the success of a super-chain owned by Joe Fox (Hanks). While chatting anonymously online, the two fall in love without realizing they have competed IRL.
The Warner Bros. film grossed more than $250 million worldwide and landed on numerous lists of the best romantic comedies of all time.
Read on for a glimpse at where the stars of You've Got Mail have gone since leaving Ephron's Upper West Side.
You've Got Mail marked the actress's third film with Ephron in just 10 years, this time as the independent children's bookshop owner, Kathleen Kelly. The part was also the third time she starred opposite Tom Hanks, previously sharing the screen with him in Sleepless in Seattle and Joe Versus the Volcano.
Ryan went on to star in a number of films throughout the 2000s, including Hanging Up, written by Delia Ephron, who penned the script for You've Got Mail with sister Nora Ephron. Ryan's later rom-com credits include Kate & Leopold, The Deal and My Mom's New Boyfriend.
In 2015, Ryan made her directorial debut with Ithaca, a wartime drama starring Hanks and her son, Jack Quaid, with an original score by John Mellencamp. In an interview with The Hollywood Reporter, Ryan cited Ephron as one of her creative influences in helming her first film.
Although Hanks had received critical acclaim and back-to-back Academy Awards for his starring roles in Forrest Gump (1994) and Philadelphia (1993), he returned to his rom-com roots to shoot his second film with Nora Ephron.
Hanks plays Joe Fox, the founder of a bookstore mega-chain that threatens to displace business at the boutique bookshop owned by Ryan's character.
Since You've Got Mail, Hanks went on to find further Hollywood success for his dramatic roles, earning praise and award nominations for 1998's Saving Private Ryan and 2001's Castaway. He later starred in Catch Me If You Can, The Da Vinci Code, Saving Mr. Banks and Captain Phillips. In addition to reprising his voice role as Woody in Toy Story 4, Hanks will soon be seen as Fred Rogers in a biopic of the Mister Rogers' Neighborhood host.
Kinnear plays Frank Navasky, Kathleen's boyfriend at the start of the film and a columnist for The New York Observer.
Kinnear went on to star in films like Little Miss Sunshine, Bad News Bears, Baby Mama and Stuck in Love. In 1998, he was nominated for an Academy Award for his role in As Good as It Gets.
In 2016, he portrayed former vice president Joe Biden in the Emmy-nominated television film, Confirmation. Kinnear recently returned to the political arena with a role in the sixth and final season of Netflix's House of Cards.
Before launching his hit Chappelle's Show, the comedian played Kevin Jackson, Joe's friend and co-worker.
In 2013, Chappelle returned to touring stand-up full-time. In 2016, he hosted the post-election episode of Saturday Night Live, for which he later won an Emmy. In 2017, Chappelle released multiple stand-up specials on Netflix. He won a Grammy for best comedy album in 2018.
He can currently be seen in Bradley Cooper's awards contender A Star Is Born.
Posey plays Patricia Eden, Joe's girlfriend at the start of the film. Joe memorably describes the aggressive publishing executive as someone who "makes coffee nervous."
In 2006, Posey starred as the titular character in Fay Grim, based on the role she originated in 1997's Henry Fool. She reprised the role in Ned Rifle, alongside Aubrey Plaza and Liam Aiken. She has since gone on to star in a number of indie films, including Broken English, Price Check, Highland Park and Columbus.
The actress also had a television stint guest starring on The Good Wife and recently starred in Netflix's Lost in Space.
Later this year, Posey will star alongside Ken Jeong in Elsewhere, an indie drama by writer-director Hernan Jimenez.
Zahn played George Pappas, a staffer in Kathleen's bookshop.
In the 1990s, Zahn made a quick cameo on Friends as Phoebe's ex-husband Duncan and starred alongside Hanks in That Thing You Do!. Since appearing in You've Got Mail, Zahn has had roles in films across all genres.
He's played a variety of comedic oddballs in films like Saving Silverman, Sahara and the Diary of a Wimpy Kid films, but has also shown a more dramatic side in Rescue Dawn and as Bad Ape in War for the Planet of the Apes, for which he donned a CGI jumpsuit.
In January he'll be seen in Valley of the Boom, National Geographic's look at the 1990s tech bubble.
Burns plays Kathleen's co-worker and friend at The Shop Around the Corner.
Burns is best known for her rom-com roles, including Cheryl Frasier — best known as Miss Rhode Island—in the Miss Congeniality films and as Meryl Brooks in Two Weeks Notice. She later played Eileen in What's Your Number? and appeared in Manchester by the Sea.
The actress also starred in the HBO Comedy series Bored to Death as Zach Galifianakis' love interest.
Burns recently finished a run in the off-Broadway play Peace for Mary Frances, giving a performance The Hollywood Reporter's Frank Scheck called "excellent."
Arguably best known for her role as All in the Family matriarch Edith Bunker, Stapleton played Birdie Conrad in You've Got Mail, Kathleen's elderly colleague and confidant.
The late actress won three Emmy awards for her performance in the popular 1970s sitcom. After You've Got Mail, she appeared in projects like The Pursuit of Happiness and Like Mother Like Son: The Strange Story of Sante and Kenny Kimes.
Stapleton was also an accomplished stage actress, starring in the original production of Damn Yankees, as well as her own one-woman show based on Eleanor Roosevelt's life, Eleanor: Her Secret Journey, in which she performed for several years since 1998.
Many actors paid tribute to Stapleton after her death in 2013. "No one gave more profound 'How to be a Human Being' lessons than Jean Stapleton," All in the Family producer Norman Lear said.
Coleman, who played Joe's father, Nelson Fox, one of the Fox Books executives, began his expansive career in the 1960s. The War Games actor starred in Rolling Thunder (1977) and Tootsie (1982) after a string of television roles, and won an Emmy for his performance in Sworn to Silence in 1987.
After You've Got Mail, Coleman voiced Principal Prickly in the animated Disney series Recess, and played Simon Baker's father in The Guardian on CBS.
Most recently, Coleman starred as Commodore Louis Kaestner on HBO's Boardwalk Empire and appeared in Warren Beatty's Rules Don't Apply (2016).