Harold Ramis Director, Screenwriter Robert De Niro Boss Paul Vitti Actor Billy Crystal Dr. Ben Sobel Actor, Executive Producer Lisa Kudrow Laura MacNamara Actor Joe Viterelli Jelly Actor Chazz Palminteri Boss Primo Sidone Actor Joseph Rigano Dominic Manetta Actor Bill Macy Dr. Isaac Sobel Actor Leo Rossi Carlo Mangano Actor Kyle Sabihy Michael Sobel Actor Rebecca Schull Dorothy Sobel Actor Molly Shannon Caroline Actor Max Casella Nicky Shivers Actor Pat Cooper Salvatore Masiello Actor Richard C. Castellano Jimmy Boots Actor Jimmie Ray Weeks FBI Agent Steadman Actor Elizabeth Bracco Marie Vitti Actor Tony Darrow Moony Actor Donnamarie Recco Sheila Actor New York Joe Catalfumo Exuberant Mourner Actor Dave Corey Miami Hall Guard Actor Kenneth Lonergan Writer, Screenwriter Peter Tolan Writer, Screenwriter Bruce Berman Executive Producer Chris Brigham Executive Producer Jane Rosenthal Producer Paula Weinstein Producer Howard Shore Original Music Stuart Dryburgh Cinematographer Craig Herring Film Editing Christopher Tellefsen Film Editing Ellen Chenoweth Casting Laura Rosenthal Casting Wynn Thomas Production Design Jefferson Sage Art Director Leslie E. Rollins Set Decoration Aude Bronson-Howard Costume Design