Set in stylised Los Angeles, Charles Swan is a playful comedy of lost love, relationships, revenge fantasies, and Brandy Alexanders. Charles (Charlie Sheen) is a successful graphic designer whose fame, money and charm have provided him with a seemingly perfect life. But when Ivana (Kathryn Winnick) the woman of his dreams leaves him, Charles falls apart, and swirls into fantasy inspired reflections upon his colourful past and the women who played a part in it. Can his best friend (Jason Schwartzman), advisor Saul (Bill Murray) and sister Izzy (Patricia Arquette) help Charles come to terms with life without Ivana?