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)