Overview
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The series revolved initially around the lives of the Harper brothers, Charlie (Charlie Sheen) and Alan (Jon Cryer), and Alan's son Jake (Angus T. Jones). Charlie is a bachelor who writes commercial jingles for a living, while leading a hedonistic lifestyle. When Alan's wife, Judith (Marin Hinkle), decides to divorce him, he moves into Charlie's Malibu beach house, with Jake coming to stay over the weekends. Charlie's housekeeper is Berta (Conchata Ferrell), a sardonic woman who initially resents the change to the household, but eventually accepts it. Charlie's one-night stand Rose (Melanie Lynskey) was first introduced as his stalker in the pilot episode.
The first five seasons find Charlie in casual sexual misadventures with numerous women until the sixth season, when he becomes engaged to Chelsea (Jennifer Taylor), but the relationship does not last, as Chelsea breaks off their engagement. Afterwards, Charlie flies to Paris with his stalker Rose in the show's de facto eighth-season finale. However, in the ninth-season premiere, Charlie is said to have died after he was struck by a Paris subway train. Rose hints that she threw Charlie into the train's path after learning that he had cheated on her.
Alan's attitude and experiences are contrasted with Charlie's. Throughout the series, Alan deals with his son Jake's growing up and the aftermath of his bitter divorce, while having little success with women. His marriage to Kandi (April Bowlby) at the end of the third season was short-lived. In the fourth season, Alan is back at the beach house paying alimony to two women out of his low earnings as a chiropractor. In the seventh season, he begins a relationship with Lyndsey McElroy (Courtney Thorne-Smith), the mother of one of Jake's friends. Their relationship is temporarily suspended when Alan cheats on her and accidentally burns down her house, but the relationship is eventually resumed.