In a small coastal California town, Henry and Nicky are pals from blue collar families with only a short time before they ship off to World War II. Henry begins romancing new-to-town Caddie Winger, believing her to be wealthy. Mischievous and irresponsible, Nicky gets into trouble which forces the other two to become involved, testing their relationship, as well as the friendship between the boys.
Sean Penn
as Henry 'Hopper' Nash
Nicolas Cage
as Nicky / Bud
Elizabeth McGovern
as Caddie Winger
John Karlen
as Mr. Nash
Rutanya Alda
as Mrs. Nash
Max Showalter
as Mr. Arthur, Piano Teacher
Crispin Glover
as Gatsby Boy
Barbara Howard
as Gatsby Girl
Bob Maroff
as Al
Carol Kane
as Annie the Hooker
Dominic Nardini
as Soldier with Annie
John Brandon
as Mr. Kaiser