Two And A Half Men

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The series centers around a freewheeling bachelor, Charlie, whose carefree lifestyle is interrupted when his newly separated brother Alan moves in along with his son, Jake.

Charlie Sheen as Charles Francis "Charlie" Harper, a hedonistic ladies' man, never married , jingle/children's song writer who tends to pick on his younger brother Alan but ultimately loves him. He is the exact opposite of his little brother: relaxed and affluent. He loves his nephew Jake and gives him advice ,but the two often trade barbs as well.

Jon Cryer as Alan Jerome Harper, Charlie's divorced chiropractor brother, who is more conscientious than his brother but continually stricken with bad luck and teased by Charlie. After losing his house to his wife, Judith, during the divorce, he permanently resides with Charlie. Then after losing his condo to his second wife Kandi, he moves back in with Charlie. He is generally a nice and polite person, but seems to have a weakness for women who treat him poorly, which may stem from the non-nurturing relationship he had with his and Charlie's mother.

Angus T. Jones as Jacob David "Jake" Harper, the underachieving son of Alan and Judith. He spends most of his free time playing video games, eating, watching television and sleeping. He loves his father and uncle but is often surly toward them.

Conchata Ferrell , as their sarcastic housekeeper Berta. Although Berta's manner may be viewed as rude, Alan and Charlie still treat her with a great deal of respect. She has a sister named Daisy, played by Camryn Manheim, with whom she does not get along. She also has a number of daughters and granddaughters, who she herself states are "sleazy and easy" and sometimes brings along to work, with the example of Prudence, who is played by Megan Fox. She has flirted with Teddy Leopold and several other men who enter the house. She has been known to attend many of the Harper family functions.

Marin Hinkle as Judith Harper, Alan's vindictive first ex-wife. She seems to despise Alan and takes any chance to humiliate him. She was the first woman Alan ever slept with, but their marriage was cold and she said that the only time she was ever happy being sexual was when she was pregnant with Jake. Alan often calls out her hypocritical behavior but also seems to still have feelings for her, going as far as having visions of her and her new husband when he began dating a mutual friend of theirs. She made no secret of living luxuriously with Alan's alimony, going as far as to get breast implants. She has since remarried to Dr. Herb Melnick (Ryan Stiles), Jake's pediatrician, a union that brought joy to Alan because it meant he no longer had to pay alimony. She still makes Alan pay child support for activities she doesn't want to trouble Herb with.

Holland Taylor as Evelyn Harper, Charlie and Alan's conceited and self-centered mother and Jake's grandmother. She expresses a superficial fondness for her sons and grandson, but rarely lives up to her outsized image of herself as a devoted and misunderstood matriarch. Her sons and grandson generally return the favor and go out of their way to avoid interacting with her on most occasions. Her wide-ranging sex life is a recurring gag throughout the series. The family frequently refers to her as "the devil", and Charlie has her number on his cell phone under the name "666".

Melanie Lynskey  as their neighbor Rose, a former girlfriend and stalker of Charlie's. She enters and exits Charlie's house by climbing onto the patio and has five ferrets, all named Charlie. Rose earned her undergraduate degree from Princeton University in two years and has a Masters Degree in behavioral psychology from Stanford University. Her family is involved in banking and oil, making them—and implicitly her—wealthy. Rose eventually left for London, England but has since returned to the U.S. and found new ways to woo and stalk Charlie. Rose's father is played by Charlie Sheen's real-life father Martin Sheen. She is shown hanging out with Alan occasionally and they get along very well.

 Ryan Stiles  as Dr. Herb Melnick, Judith's new husband and Jake's new stepfather. Though he is married to Judith, he is a laid-back guy and he and Alan seem to get along, and he seems to envy aspects of the Harper brothers' lives . Alan is just happy that he no longer has to pay Judith alimony, as she used it for selfish purposes. An inconsistency in the story line is the first time he appears, he is named as Greg. While Herb and Judith separated, and Alan had sex with her. Herb eventually got back together with Judith because he was scared of changing. It was later revealed that Judith became pregnant around the time she and Alan had sex. Herb remained ignorant of all of this.

April Bowlby  as Kandi, Alan's young, dimwitted ex-girlfriend. After an impromptu wedding in Las Vegas, Kandi divorced him and kept their condo but they continued to have a semi-regular sexual relationship.