Andrew McCarthy as Clifford Godfrey

Kelly Preston as Amanda

Helen Hunt as Clare Enfield

Daniel Roebuck as Marty

Tom McFadden as Mr. Ross

Joel Murray as Bert

Liz Sheridan as Mrs. Stein

Monty Ash as Mr. Stein

Marsha Dietlein as Mrs. Lipman

Elvis Ballasteros as Sam (Chicago Bartender)

Stephen O'Connell as Drunk in Bar

Morrie Eisenman as Detective in Bar

Danny Mora as Hotel Manager

Gloria Kisel as Francine

Shawndell Bryant as Eddie

Michael Ciotti as Lumpy

Demetre Phillips as Dimitri

Christie Mellor as Mrs. Zucker

James F. Dean as Mr. Zucker

Courtland Mead as Frank Jr.

Peter Koch as Anthony

Adam Mills as Adam

Will McAllister as Elderly Diver

Pepe Serna as Dock Official

Jeff Schuetze as Hotel Messenger

Jesse Dizon as Maitre d'

Roberto Estrada as Mariachi Singer

Reni Santoni as Rueben the Bartender

Eric Scott Pearl as Photographer at Party

Kid Creole as Self

Janique Svedberg as Coconut #1

Taryn Rose as Coconut #2

Adriana Kaegi as Coconut #3

Sara Peery as Flight Attendant

Archie Hahn as Gentleman on Plane

Irene Olga López as Maid

Denny Dillon as Sunray Tours Travel Agent

Will McFadden as Stevie Johnson

Garth Yimkee as Mr. Johnson

Robin Duke as Mrs. Johnson

Brian Boru Gleeson as Larry Johnson

Linda Griffin as Woman Shopper

Keven McCauley as Target Security Guard

Ozzie Zornizer as Mexican Deejay

Lindsay Garrison as Clifford's Daughter (uncredited)