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The show initially centers on seven characters: brothers Charlie and Alan Harper ; Jake Harper, the dimwitted 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 wealthy, five time widowed, bisexual mother, and Jake's grandmother; and last of all, Berta, Charlie's sharp-tongued housekeeper, who later joins the main cast starting with season two after playing a major recurring role throughout the first season. In season nine, the show is revamped when Charlie is struck and killed by a moving train. Walden Schmidt replaces him as the new owner of the beach house, a recently divorced internet billionaire. In season eleven, Jake moves to Japan and leaves the series, so to replace "the half-man", Charlie's long-lost-daughter moves into the beach house after looking for her late father. The show also features numerous supporting characters, each of whom plays a prominent role in a small group of episodes. He is a womanizing bachelor who tended to abuse his younger brother Alan, whom he loved dearly, although he would have never admitted it, and usually took pleasure in any misfortune or trouble he runs into.

Phoebe Waller-Bridge is another one of s funniest women - and she has the Emmys to prove it. Meanwhile, Tracee Ellis Ross has earned the title of one of the most comical sitcom actresses of the s, with her roles in Black-ish and Mixed-ish. Nicole Byer is another of the funny women of the decade.

Jon Cryer portrayed the character for the entire duration of the series, the only original main cast member to do so. Alan is a chiropractor , the hapless father of Jake Harper , roommate and best friend of Walden Schmidt , ex-husband of Judith Harper-Melnick and the surviving younger brother of Charlie Harper. He may also be the father of Milly Melnick. Also got his pee pee licked and butthole filled by Walden Schmidt. According to Eric Tannenbaum, executive producer on the show, Alan Harper is loosely based on his real life friend Stephen Deane.