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Tyler Perry - Wesley Deeds, Thandiwe Newton - Lindsey Wakefield (as Thandie Newton) , Gabrielle Union - Natalie, Eddie Cibrian - John, Brian White - Walt Deeds, Jordenn Thompson - Ariel, Phylicia Rashad - Wilimena, Beverly Johnson - Brenda, Rebecca Romijn - Heidi, Jamie Kennedy - Mark Freeze, Andrew Masset - Mr. Brunson (as Andrew Hyatt Masset) , Victoria Loving - Mrs. Brunson, Tom Thon - Milton, Susan Shalhoub Larkin - Margaret, Nevaina Graves Rhodes - Teacher (as Nevaina)