Whaley's third film as writer and director, "New York City Serenade", starring Chris Klein and Freddie Prinze Jr., premiered at the 2007 Toronto International Film Festival. He stars as the villain in the 2007 horror film "Vacancy". In 2014 he wrote and directed the film "Like Sunday, Like Rain", starring Debra Messing, Leighton Meester and Billie Joe Armstrong. The film won six awards at the 2014 Williamsburg Independent Film Festival including Best Film, Best Director and acting nods for Armstrong, Meester, Messing and Julian Shatkin. It opened in March 2015.