In "You've Got Mail," Hanks' character, Joe, is a third-generation businessman who opens a commercial chain bookstore called Fox Books on Manhattan's Upper West Side.

By the time Hanks — one of America's favorite actors — landed the part, he had been appearing in movies and TV for nearly 20 years, beginning with roles in sitcoms like ABC's "Bosom Buddies" and NBC's "Family Ties."

In the 1990s, Hanks impressively earned two consecutive Oscars for his performances in the dramas "Philadelphia" (1993) and "Forrest Gump" (1994), which was based on Winston Groom's novel of the same name.

He also received best actor award nominations for "Big" (1988) and "Saving Private Ryan" (1998).

In addition to appearing in the baseball film "A League of Their Own" (1992) and the NASA biopic "Apollo 13" (1995), Hanks was in "Sleepless in Seattle" (1993), another iconic Ephron rom-com in which he starred opposite Ryan.

Additionally, he voiced Woody, a Wild West action figure, in Pixar's "Toy Story" (1995).

Following "You've Got Mail," Hanks had starring roles in late-1990s and early-2000s hits such as "The Green Mile" (1999), "Cast Away" (2000), and "Catch Me If You Can" (2002). 

He also lent his voice to the conductor in "The Polar Express" (2004) and reprised his role as Woody in all the "Toy Story" sequels, most recently "Toy Story 4" (2019). 

Hanks has notably portrayed a number of real-life figures on the screen, too.

He played Walt Disney in "Saving Mr. Banks" (2013), pilot Chesley Sullenberger in "Sully" (2016), Washington Post editor Ben Bradlee in "The Post" (2017), and Fred Rogers in "A Beautiful Day in the Neighborhood" (2019), which scored him an Academy Award nomination.

He also held roles in the Apple TV+ war drama "Greyhound" (2020) and Amazon's "Borat Subsequent Moviefilm" (2020). 

His most recent projects include "Elvis" (2022), Disney's live-action "Pinocchio" (2022), "A Man Called Otto" (2022), and "The Bloody Hundredth" (2024). 

Ryan played Kathleen, the owner of an independent children's bookstore called The Shop Around the Corner. After joining an over-30 chat room online, Kathleen unknowingly starts an epistolary romance with Joe, her business rival. 

Like Hanks, Ryan began professionally acting in the early 1980s.

Some of her first credits include lead roles in the long-running CBS soap opera "As the World Turns" — her character, Betsy Stewart, was a fan favorite whose on-screen wedding garnered 20 million viewers — and in the Western ABC series "Wildside."

Leaving TV for Hollywood, Ryan had a supporting part in "Top Gun" (1986) as Nick "Goose" Bradshaw's wife, Carole. But it was her roles in romantic comedies that earned her a reputation as "America's sweetheart." 

Opposite Billy Crystal, she charmed viewers in Rob Reiner's friends-to-lovers romance "When Harry Met Sally…" (1989). In "Sleepless in Seattle," she played a journalist who falls for a single dad (Hanks) after his young son calls into a radio talk show.

Ryan went on to star in the drama "When a Man Loves a Woman" (1994) and appeared opposite Nicolas Cage in the romantic fantasy "City of Angels" (1998).

She also provided the speaking voice for the title character in "Anastasia" (1997), the animated musical inspired by the Russian royal family. 

In 2001, Ryan starred in "Kate and Leopold," a romantic drama that centers on a 19th-century duke (Hugh Jackman) who time-travels to present-day New York.

A few years later, she pivoted to roles in independent films such as "In the Land of Women" (2007) and "Serious Moonlight" (2009).

Ryan's projects in the 2010s have ranged from Lisa Kudrow's improvisational Showtime comedy series "Web Therapy" about a psychologist's teletherapy practice to the film "Fan Girl" (2015), which stars Kiernan Shipka as a teen who wants to make a movie about All Time Low, her favorite band. 

On top of making her directorial debut with "Ithaca" (2015), a drama based on William Saroyan's novel "The Human Comedy," she also starred in it alongside Hanks and her son, Jack Quaid.

She most recently directed and starred alongside David Duchovny in a romantic comedy called "What Happens Later" (2023).

Although better known as a comedian, Chappelle had several film credits to his name by the time he played Kevin, Joe's best friend and a store manager at Fox Books.

Chappelle was in Mel Brooks' musical parody "Robin Hood: Men in Tights" (1993) and the 1996 remake of the sci-fi comedy "The Nutty Professor."

He also appeared in the action-thriller "Con Air" (1997). 

Chappelle recorded his first hourlong HBO stand-up special, "Dave Chappelle: Killin' Them Softly," in 2000.

Three years later, he launched "Chappelle's Show," a weekly sketch series on Comedy Central that aired until 2006. 

In addition to touring his stand-up act around the country, he has earned three consecutive Grammy awards for best comedy album. 

Although mainly focusing on stand-up, Chappelle still acts from time to time. He played Morris in Spike Lee's "Chi-Raq" (2015) and George "Noodles" Stone in "A Star is Born" (2018). 

In recent years, he has appeared in his own TV comedy specials.

Kinnear played Kathleen's boyfriend, Frank, a New York Observer writer who loves analog technology, especially typewriters, and decries the computer revolution. 

Kinnear had a number of small parts in shows and in made-for-TV movies in the late 1980s before making his feature-film debut in the superhero parody "Blankman" (1994).

His first major role was in Sydney Pollack's remake of the romantic drama "Sabrina" (1995) opposite Harrison Ford and Julia Ormond. 

In 1997, he starred in "As Good as It Gets" as Simon Bishop, a painter who lives next door to a reclusive romance novelist (Jack Nicholson). Kinnear earned his first and only Oscar nomination to date for that performance. 

Kinnear's biggest roles in the 2000s spanned from baseball coach Roy Bullock in Richard Linklater's remake of "Bad News Bears" (2005) to pageant dad Richard Hoover in the hit independent film "Little Miss Sunshine."

He also played Tina Fey's romantic interest in "Baby Mama" (2008). 

He also starred as Jack Kennedy in Reelz's "The Kennedys," played billionaire Bill Shepherd in season six of Netflix's "House of Cards," and made a cameo as himself in Netflix's "Unbreakable Kimmy Schmidt."

Additionally, he portrayed a young Joe Biden in "Confirmation" (2016), which chronicles Clarence Thomas' Supreme Court nomination hearings, and has starred in festival-favorite indies such as "Little Men" (2016) and "Brigsby Bear" (2017). 

Kinnear appeared in the thriller "Dreamland (2019)," costarring Armie Hammer, Gary Oldman, and Lily-Rose Depp. He also held roles in the Apple TV series "Black Bird" and season four of Netflix's "You."

Posey played one of the most misunderstood characters in "You've Got Mail" — Patricia, a high-powered book editor who Joe dates for most of the movie. 

Despite coming off as aloof and self-absorbed, the ambitious Patricia offers to give Kathleen a job when The Shop Around the Corner is jeopardized by Fox Books. 

Posey gained name recognition in the 1990s from appearing in Richard Linklater's "Dazed and Confused" (1993), "Kicking and Screaming" (1995), and the cult classic "Party Girl" (1995). 

She also portrayed art dealer Mary Boone in the biopic "Basquiat" (1996) and starred in the mockumentary "Waiting for Guffman" (1997). 

Posey's movie roles in the 2000s ranged from Fiona, a conspiracy-spouting record company executive, in "Josie and the Pussycats" (2001) to Kitty Kowalski, Lex Luthor's nurse and eventual girlfriend, in "Superman Returns" (2006). 

More recently, she appeared in Woody Allen's "Café Society" (2016), a romantic drama set in the 1930s, and "Columbus" (2017), filmmaker Kogonada's feature directorial debut. 

Posey also starred as June Harris, also known as Dr. Smith, in the Netflix sci-fi reboot "Lost in Space," which aired from 2018 to 2021. 

She has also played recurring parts in ABC's "Boston Legal," CBS' "The Good Wife," and TBS-HBO's "Search Party" in addition to making guest appearances on series like NBC's "Will and Grace," "Parks and Recreation," and "New Girl."

Posey also played Blair in AMC's "Tales of the Walking Dead" and is set to appear in season three of HBO Max's "The White Lotus."

Zahn played goofy bookseller George in "You've Got Mail." 

Prior to acting on screen, Zahn cut his teeth onstage. In 1991, he helped form the Malaparte Theatre Company with Ethan Hawke and playwright Jonathan Marc Sherman. The collective focused on works about male anxiety.

In 1994, he appeared with Hawke in the cult classic "Reality Bites," a film focusing on recent college grads in Houston.

He also starred alongside Hanks in "That Thing You Do!" (1996), Hanks' directorial debut about a fictional 1960s band.

Zahn provided the voice for the cat Monty in "Stuart Little" (1999), played Rosencrantz in Michael Almereyda's contemporary version of "Hamlet" (2000), and starred as Drew Barrymore's ex in the coming-of-age film "Riding in Cars with Boys" (2001). 

His movie roles in the 2010s have included parts in "Dallas Buyers Club" (2013), "Captain Fantastic" (2016), "Where'd You Go, Bernadette" (2019), and the "Diary of a Wimpy Kid" film series, based on the books by Jeff Kinney. 

Also known for his work as a TV actor, Zahn starred in the New Orleans-set HBO drama "Treme" as Davis McAlary and in the ABC sci-fi thriller "The Crossing" as Jude Ellis.

Additionally, he played the Dunphys' neighbor, Ronnie, in ABC's "Modern Family."

Zahn also voiced an emotional support dog that helps an anxious preteen in Netflix's family comedy "The Healing Powers of Dude." Zahn appeared as Mark, a father with an inferiority complex, in season one of HBO Max's "The White Lotus" and most recently held a role in season two of the Apple TV+ show "Silo."

Burns played Christina Plutzker, George's droll coworker at the bookstore.

Before appearing in "You've Got Mail," Burns had small parts in NBC's "Law and Order" and ABC-Hulu's soap opera "One Life to Live." 

Burns has acted in multiple films with Sandra Bullock, beginning with her performance as Miss Rhode Island, Cheryl, in "Miss Congeniality" and continuing with "Two Weeks Notice" (2002) and "Miss Congeniality 2: Armed and Fabulous" (2005).

She is also known for her roles in "Bewitched" (2005) and "What's Your Number?" (2011). 

Burns also starred in the HBO comedy "Bored to Death" and the NBC sitcom "Save Me."

She also had recurring roles and guest parts in shows such as NBC's "Blindspot," Amazon's "Sneaky Pete," and Netflix's "The Politician." 

She appeared most recently in an episode of the timely Netflix anthology "Social Distance." Since then, she's held roles in the Paramount+ drama "The Good Fight" and HBO Max's "Julia."

Stapleton played Birdie, the eccentric and sage bookkeeper at The Shop Around the Corner who Kathleen confides in about her personal life. 

Stapleton, who had a background in theater, began acting in movies and TV shows in the 1950s. Her first film role was in the musical "Damn Yankees" (1958).

She went on to star in "Up the Down Staircase" (1967), a drama based on the novel of the same name by Bel Kaufman.

She's perhaps best known for her role as matriarch Edith Bunker in the CBS sitcom "All in the Family," which earned her three Emmys.

She  guest-starred in hit CBS series in the 1990s and early 2000s like "Murphy Brown," "Everybody Loves Raymond," and "Touched By an Angel." 

In 2013, Stapleton died of natural causes at age 90. Her final movies included the direct-to-video sequel "Pocahontas 2: Journey to a New World" (1998) and the rom-com "Pursuit of Happiness" (2001).

This story was originally published in December 2020 and most recently updated on December 18, 2024.