Charlie Harper (Charlie Sheen) is a well-to-do bachelor with a house at the beach, a Mercedes in the garage and an easy way with women. His casual Malibu lifestyle is interrupted when his tightly wound brother, Alan (Jon Cryer), and Alan's son, Jake (Angus T. Jones), come to stay with him.

Complicating matters further are Charlie and Alan's narcissistic, emotionally toxic mother, Evelyn (Holland Taylor); Alan's deezply neurotic ex-wife, Judith (Marin Hinkle); Charlie's domineering, unapologetically blue-collar housekeeper, Berta (Conchata Ferrell); and Rose (Melanie Lynskey), a brilliantly manipulative and vaguely crazy neighbor who had a brief fling with Charlie, is obsessed with him and is determined to stay in his life by whatever means necessary.

Despite the complexities of their lives and their own strained relationship, Charlie and Alan have one thing in common -- they both love Jake and want what's best for him. As a result, they manage to create a little family unit that promises to make each of them a better man.