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Lindsay Lohan Casey Stuart Tyra Banks Eve Jere Burns Ben Stuart Anne Marie DeLuise Drew McDonald Garwin Sanford Richie Tom Butler Phil Jillian Fargey Ellen Katelyn Wallace Sarah Shaina Tianne Unger Jessica Stephanie Moore Woman in Mink Dee Jay Jackson Coach Corrine Koslo Toy Store Owner Alf Humphreys Bookstore Owner (as Alfred E. Humphreys) Kerry Sandomirsky Ms. Weiner Sam MacMillan Sam Jessica Lee Owens Shannon Chantal Strand Sarah's Sister Laurie Murdoch Mr. Boring Candice Connelly Mrs. Boring Alvin Sanders Guard Ryan DeBoer Weiner (as Ryan de Boer) Lesley Ewen Francine Kaitlyn Burke Girl with Doll George Blondheim Band Leader Joanna Piros Newscaster Campbell Lane Judge Peterman Kasper Michaels Litter Man Garvin Cross Truck Driver Aliana Lohan Girl at Football Stands (uncredited)