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The show initially centers on seven characters: the brothers Charlie and Alan Harper; Jake Harper, the son of Alan and his first ex-wife; Judith Harper-Melnick, Alan's first ex-wife, Herb's ex-wife, and Jake and Milly's mother; Rose, one of Charlie's previous one-night stands who continuously stalks him; Evelyn Harper, Charlie and Alan's ...
Bill (Chris O'Donnell) was a previous girlfriend of Charlie's appearing in a season one episode, "An Old Flame with a New Wick". Bill had since had sexual-reassignment surgery and was formerly living as Jill. Charlie comments during the episode that while the relationship was passionate, sex with Bill was "a little weird".
Richards recurred as Charlie’s ex-girlfriend Lisa (Season 1, Episode 10); Kunis played free-spirit Vivian (Season 11, Episode 19). ALLISON JANNEY & JAIME PRESSLY
Originally starring Charlie Sheen in the lead role alongside Jon Cryer and Angus T. Jones, the series was about a hedonistic jingle writer, Charlie Harper, his uptight brother, Alan, and Alan's mischievous son, Jake. As Alan's marriage falls apart and divorce appears imminent, he and Jake move into Charlie's beachfront Malibu house and ...
Charlie writes children's songs and finds success as Charlie Waffles. The kids and their parents love him, even signing CDs of his jingles. However, Charlie's newfound fame irritates Alan, and Charlie has a high-proof answer to his sudden stage fright, getting drunk, which actually works out, finding a huge fame at the live audience.
Charlie accuses Alan of being cheap, ends up angrily throwing him out of the house, so Alan and Jake temporarily stay with a friendly Herb and angry Judith. But after Herb bonds with Charlie and Alan crosses a line with Judith, she takes measures to reset the situation, forcing Alan to apologize to Charlie and forcing Charlie to take him back.
That role was billed to Charlie Sheen for most of the show’s run. Sheen was by far the highest-paid actor on the show, commanding a sky-high $800,000-per-episode salary from the very first season.
When Charlie leaves the house to avoid a date that he can't stand, he ends up at a coffee shop, where he reconnects with his old girlfriend Lisa (Denise Richards), now a divorcée with a child. Meanwhile, Alan walks in on Charlie's date in the shower and she frighteningly attacks him and Jake uses this situation to blackmail Alan; Jake tries ...