Charlie Harper (series star 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. But his casual Malibu lifestyle was interrupted when his tightly wound brother, Alan (series star Jon Cryer), and Alan's son, Jake (series star Angus T. Jones), came to stay with him. Complicating matters further are Charlie and Alan's narcissistic, emotionally toxic mother, Evelyn (series star Holland Taylor); Alan's deeply neurotic ex- wife, Judith (series star Marin Hinkle); Charlie's domineering, unapologetically blue-collar housekeeper, Berta (series star Conchata Ferrell); and Rose (recurring guest star Melanie Lynskey), a brilliantly manipulative and vaguely crazy neighbor who had a brief fling with Charlie, remains 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. In the season premiere, Charlie deals with the immediate aftermath of his canceled wedding--and Alan's impulsive new marriage to 22-year-old Kandi (series star April Bowlby). Still in Las Vegas, Alan and his materialistic bride find out that Alan's lucky streak is not over when he wins $500,000 on one play of a slot machine. Four months later, Alan visits his brother's home to find that Charlie is taking full advantage of having the house all to himself. But Alan has some life-altering news to share: he's getting divorced.
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