Chelsea Handler is a comedian, television host, and seven-time New York Times best-selling author whose humor and candor have established her as one of the most celebrated voices in entertainment and pop culture.

WANDA SYKES is an Emmy winning stand up comic, writer, actress and producer who has been entertaining audiences for over twenty years. She has ranked among Entertainment Weekly's “25 Funniest People in America” and her peers have called her “one of the funniest stand-up comics” in the field.

In this special episode of Ariel Emanuel and Ben Persky’s “Rushmore” series, where titans across sports, entertainment and technology debate the greatest of all time across...