Winsome Sinclair served as a casting director for television series and films. She cast episodes of Being Mary Jane, Truth Unspoken Series, A Luv Tale: The Series, ABC Afterschool Specials, American Playhouse, New York Undercover and Chappelle's Show. Sinclair cast television movies including "Bessie," "Seasons of Love," "In the Gloaming" and "Strapped."

She worked in the casting department for several films including "Malcolm X," "Juice," "Precious," "Inside Man," "Pariah" and "Cadillac Records."