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The film first premiered on June 25, 1993.
Meg recently starred alongside Tom Hanks in Ithaca, which was their fourth film together. They previously starred in Joe vs. the Volcano, You've Got Mail, and of course, Sleepless in Seattle.
Fun fact: Julia Roberts was almost cast as Annie, but turned it down.
Bill, who played Annie's jilted fiancé in Sleepless, most recently starred in the Golden Globe-nominated film Battle of the Sexes.
Fun fact: Bill originally thought his role would be bigger and that Walter would be in a love triangle, like in A Philadelphia Story.
After his role in Sleepless, Ross continued acting and even had a recurring role in Party of Five. His last role was in 2006, when he guest starred in an episode of Without a Trace. He's been pretty under the radar, so here's a photo of him from about 10 years ago.
Fun fact: From 1997-1998, Ross voiced T.J. in the TV show Recess.
Rob most recently starred alongside Adam Sandler in the Netflix film Sandy Wexler. He also had a recurring arc on New Girl.
Fun fact: During the movie, Rob's character Jay mentions tiramisu and Sam, unaware that it's a dessert, thinks it's a sexual act. After the film premiered, the studio was flooded with calls from people wanting to know what tiramisu was. (Keep in mind, this is pre-Google.)
Rosie most recently starred in The Fosters and the Golden Globe-nominated series SMILF.
Fun fact: When Nora Ephron was casting for the role of Becky, she mentioned Rosie's name to her son, who happened to be a big fan of hers; this helped her get the role.
Gaby currently stars in Amazon's Transparent.
Fun fact: She had a huge crush on Ray Liotta when they starred in Field of Dreams.
Victor has starred in countless films, including Legally Blonde and Titanic, but was most recently cast in the Broadway revival of Hello, Dolly!
Fun fact: The scene where he cries discussing The Dirty Dozen in Sleepless was completely improvised.
Rita was most recently featured in My Big Fat Greek Wedding 2.
Fun fact: Two years after Sleepless in Seattle, Rita starred in Now and Then, alongside her Sleepless co-stars, Gaby Hoffmann and Rosie O'Donnell.
Barbara's recent roles include Blue Jasmine and You're Killing Me Susana.
Fun fact: Barbara had a recurring arc on One Life to Live and narrated the very final episode of the series.