Andrew McCarthy

Clifford Godfrey

Kelly Preston

Amanda

Helen Hunt

Clare Enfield

Daniel Roebuck

Marty

Tom McFadden

Mr. Ross

Joel Murray

Bert

Liz Sheridan

Mrs. Stein

Monty Ash

Mr. Stein

Marsha Dietlein

Mrs. Lipman

Elvis Ballasteros

Sam (Chicago Bartender)

Stephen O'Connell

Drunk in Bar

Morrie Eisenman

Detective in Bar

Danny Mora

Hotel Manager

Gloria Kisel

Francine

Shawndell Bryant

Eddie

Michael Ciotti

Lumpy

Demetre Phillips

Dimitri

Christie Mellor

Mrs. Zucker

James F. Dean

Mr. Zucker

Courtland Mead

Frank Jr.

Peter Koch

Anthony

Adam Mills

Adam

Will McAllister

Elderly Diver

Pepe Serna

Dock Official

Jeff Schuetze

Hotel Messenger

Jesse Dizon

Maitre d'

Roberto Estrada

Mariachi Singer

Reni Santoni

Rueben the Bartender

Eric Scott Pearl

Photographer at Party

Kid Creole

Self

Janique Svedberg

Coconut #1

Taryn Rose

Coconut #2

Adriana Kaegi

Coconut #3

Sara Peery

Flight Attendant

Archie Hahn

Gentleman on Plane

Irene Olga López

Maid

Denny Dillon

Sunray Tours Travel Agent

Will McFadden

Stevie Johnson

Garth Yimkee

Mr. Johnson

Robin Duke

Mrs. Johnson

Brian Boru Gleeson

Larry Johnson

Linda Griffin

Woman Shopper

Keven McCauley

Target Security Guard

Ozzie Zornizer

Mexican Deejay

Lindsay Garrison

Clifford's Daughter (uncredited)