Hope Floats
Whitaker continued his directing career with the 1998 romantic comedy, "Hope Floats", starring Sandra Bullock and Harry Connick, Jr., which he also executive produced. He directed Katie Holmes in the romantic comedy, "First Daughter" in 2004, while also serving as an executive producer on the film; he had previously co-starred with Holmes in "Phone Booth" in 2002. He gained experience as the executive producer of several made-for-television movies, most notably the 2002 Emmy-award-winning "Door to Door", starring William H. Macy.