After a brief flash-forward to Frank Sinatra as an old man, saying "I miss my guys," the movie's main narrative begins during high points in the solo careers of the Rat Pack: Dean Martin has become a big success despite the breakup of his partnership with Jerry Lewis; Sinatra's career is at its peak; Sammy Davis, Jr., is making a comeback after a near fatal car crash, and standup comic Joey Bishop is gaining exposure as an opening act for the other three. The Pack becomes complete when Sinatra reconciles with actor Peter Lawford, who has been ostracized since being seen out publicly with Sinatra's ex-wife, Ava Gardner.
Ray Liotta
as Frank Sinatra
Joe Mantegna
as Dean Martin
Don Cheadle
as Sammy Davis Jr.
Angus Macfadyen
as Peter Lawford
William Petersen
as John F. Kennedy
Zeljko Ivanek
as Bobby Kennedy
Bobby Slayton
as Joey Bishop
Megan Dodds
as May Britt
Deborah Kara Unger
as Ava Gardner
Veronica Cartwright
as Rocky Cooper
Dan O'Herlihy
as Joe Kennedy
Robert Miranda
as Momo Giancana
