Originally from Iowa Falls, Whitesell attended Simpson College before moving to New York to study acting and directing at Circle in the Square. His theater credits include Happily Ever After, And That's the Way it Was and Solo for two Voices. He worked at The Writer's Theater, the Princeton McCarter Theater and the Williamstown Theatre Festival.
In 1964 he moved on to television directing. Starting with Another World, television would prove a prosperous and healthy environment for Whitesell who went on to work on such series as A Different World, Roseanne, Coach, Law & Order, Blossom, The Cosby Mysteries, Pearl, Costello, Providence and Jack & Jill. He has even won an Emmy for his work on Guiding Light.
Whitesell decided to take a leap into feature work, directing 1993's Calendar Girl, starring Jason Priestley and Jerry O'Connell. But when the film bombed, Whitesell retreated back into television. He wouldn't resurface into the film industry until 2001 with his second feature, the comedy See Spot Run, starring David Arquette and Michael Clarke Duncan, followed by Malibu's Most Wanted (2003) starring Jamie Kennedy; Big Momma's House 2 (2006) starring Martin Lawrence; Deck the Halls (2006), starring Matthew Broderick and Big Mommas: Like Father, Like Son (2011) .