The Emmy®-winning laughfest continues as television’s leading comedy. With Jake (Angus T. Jones) now entering junior high school, his dad, Alan (Jon Cryer), reliving his high school dating history and Charlie (Charlie Sheen) finally maturing a little himself, will there be room for three men in Charlie’s Malibu beach pad? You won’t want to miss a single episode from this hilarious season!
In the fifth season premiere, Charlie and Alan try to prepare Jake for his first day of junior high school -- but they might end up traumatizing him instead.
Charlie reacts oddly after an evening with his mother. And Alan's date, Sharon (JANEANE GAROFALO - "The Larry Sanders Show," "The West Wing"), reacts oddly after having sex with Alan.
Tired of dating vapid young women, Charlie allows Alan to introduce him to a sophisticated, intelligent municipal court judge, Linda.
In the landmark 100th episode, Charlie gets closer to consummating his relationship with Linda, but he keeps seeing Rose's face everywhere he turns.
Charlie has to find creative ways to entertain the 4-year-old son of his girlfriend, Linda (recurring guest star MING WEN). Meanwhile, Alan becomes a human "guinea pig."
Charlie's girlfriend, Linda (recurring guest star MING WEN), is embarrassed to be seen in public with him. Meanwhile, despite Alan forbidding it, Jake sneaks out to a concert.
Charlie and Alan argue over Alan's place in the house, prompting Alan and Jake to move in with Evelyn. Recurring guest star ROBERT WAGNER appears as Teddy, Evelyn's boyfriend.
Charlie finds success as a children's singing star, making Alan miserable. Guest star RICHARD KIND ("Spin City") appears as Artie, an executive at Charlie's record label.
After Evelyn and Teddy become engaged, Charlie struggles to fight his attraction to Teddy's daughter, Courtney, Charlie's soon-to-be stepsister.
While trying to help Jake get over a breakup, Alan discovers that it was Charlie who stole his high school girlfriend. Alan seeks revenge on Charlie.
Seeing Alan not fully passionate about his relationship, Charlie coaches Alan in the fine art of breaking up with a woman.
Rose (recurring guest star MELANIE LYNSKEY), Charlie's lovable stalker, is back from England and takes strange care of a very sick Charlie.
Alan dates one of his ex-wife's friends who reveals a secret about Judith's sex life. Recurring guest star RYAN STILES appears as Judith's second husband.
Charlie goes with Jake on a double date and sets Alan up with a prostitute. Recurring guest star MELANIE LYNSKEY appears as Rose.
Alan worries that Charlie's womanizing is out of control. JANE LYNCH returns as Charlie's therapist, and EMMANUELLE VAUGIER returns as Charlie's former fiancée, Mia.
Alan plans Evelyn's wedding to Teddy (ROBERT WAGNER), while Charlie pursues his future stepsister and Teddy's devious daughter, Courtney (JENNY McCARTHY).
A CSI team investigates a mysterious death at Charlie's house. George Eads ("CSI: Crime Scene Investigation") makes a cameo appearance.
Charlie finds himself attracted to Angie (recurring guest star SUSAN BLAKELY), an older woman who writes self-help books. Meanwhile, Alan and Jake battle over a school assignment.
Charlie tries to resist temptation when he meets the grown daughter of the woman he's dating (SUSAN BLAKELY) and realizes they've met before. JANE LYNCH guest stars as Dr. Freeman.