For eight seasons, Charlie Harper was the unapologetically terrible heart of Two and a Half Men. Played by Charlie Sheen, the Malibu womanizer could turn practically any bad decision into a punchline, whether he was drinking, gambling, sleeping with women he absolutely shouldn’t have been sleeping with, or finding new ways to torment his younger brother Alan (Jon Cryer). Charlie was selfish, immature and frequently awful, but he was also the character who gave the sitcom its distinctive identity.
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