Cast of You've Got Mail

Tom Hanks plays Joe Fox, a charming businessman who finds himself falling in love with a woman he meets online, unknowingly not realizing she is his business rival.

Meg Ryan portrays Kathleen Kelly, a sweet and idealistic owner of a small independent bookstore who begins an anonymous online friendship with a man she later discovers is her business competitor.

Greg Kinnear takes on the role of Frank Navasky, Kathleen's writer boyfriend who questions the traditional values of Joe's big bookstore chain and its impact on the community.

Parker Posey plays Patricia Eden, Joe's stylish and high-powered girlfriend whose sophisticated lifestyle contrasts with Kathleen's more down-to-earth charm.

Steve Zahn is George Pappas, Joe's loyal and easygoing friend who provides comic relief and support in navigating both his personal and professional relationships.

Dave Chappelle portrays Kevin Jackson, Joe's witty and street-smart business partner who offers advice and a different perspective on love and relationships.

Dabney Coleman plays Nelson Fox, Joe's pragmatic and traditional father who struggles to adapt to the changing dynamics of the book industry and his son's romantic pursuits.

Jean Stapleton is Birdie Conrad, the wise and kind-hearted employee at Kathleen's bookstore who provides valuable insights and steadfast support to her during challenging times.

Heather Burns portrays Christina Plutzker, Kathleen's quirky and lovable employee who adds humor and warmth to the bookstore's atmosphere with her unique personality.

John Randolph plays Schulyer Fox, Joe's grandfather who shares wisdom and fond memories with his family while observing the changing landscape of technology and relationships.

Hallee Hirsh is Annabelle Fox, Joe's precocious and inquisitive niece who forms a special bond with Kathleen and adds a youthful perspective on family and love.

Jeffrey Scaperrotta portrays Matt Fox, Joe's young son who navigates the complexities of his parent's relationship and forms a connection with Kathleen through their shared love of books.