John Cusack Walter "Gib" Gibson Daphne Zuniga Alison Bradbury Anthony Edwards Lance Boyd Gaines Jason Tim Robbins Gary Cooper Lisa Jane Persky Mary Ann Webster Viveca Lindfors Professor Taub Nicollette Sheridan The Sure Thing Sarah Buxton Sharon John Putch Mastin Steve Pink Football Player Tracy Reiner Alison's Friend Robert Bauer Moke Frantz Turner Cop Garry Goodrow Pick-Up Driver Carmen Filpi Bus Station Bum Richard Hamilton Bartender George Memmoli Man in Bar Stephanie Blake Barmaid (as Rosalind Moreland) Sunshine Parker Cowboy Guy Fran Ryan Lady in Car Larry Hankin Trucker Julie Ow Girl in Sarong John Richard Petersen Frat Guy on Stairs (uncredited) Tamara Carrera Fantasy Girl (uncredited)