The Last International Playboy (2009)

Jack Frosts playboy lifestyle in New York City is rocked by the news that his childhood love is engaged. Amidst his friendships with Scotch Evans, a ribald nightlife correspondent; Ozzy, a troubled but loving heroin addict; and Kate Hardwick, a bewitching, quick-witted reporter, Jack sinks deeper into depression. Haunted by lost-love and his mothers suicide, Jack plunges into whiskey and self-destruction . . . until his eleven-year-old neighbor, Sophie, an unlikely mother figure, leads Jack back into himself, and out of the nostalgia and excess that consumed him.