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.
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'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 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."
In the landmark 100th episode, Charlie gets closer to consummating his relationship with Linda, but he keeps seeing Rose's face everywhere he turns. Recurring guest star JANE LYNCH appears as Dr. Freeman.
Tired of dating vapid young women, Charlie allows Alan to introduce him to a sophisticated, intelligent municipal court judge, Linda.
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.
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.
Televisions #1 comedy celebrates five seasons of funny with big laughs and hilarious new storylines. Charlie (Charlie Sheen) tops the charts as kiddie-song sensation Charlie Waffles. Alan (Jon Cryer) at last meets the perfect woman who just happens to be dating Charlie. Jake (Angus T. Jones) starts junior high, armed with reams of "helpful" advice from Alan and Charlie. Evelyn (Holland Taylor) ties the knot for the fifth time (lots of guests at the wedding, lots of cops at the reception). And as always, Berta (Conchata Ferrell) deals with it all by dealing out a royal flush of deadpan zingers. The guys are in and the welcome mat is out at everyones favorite Malibu beach house. Have a great time!
Charlie and Alan must confront their "daddy issues" when Evelyn's new boyfriend, Teddy (Robert Wagner - "Hart to Hart"), invites them to Las Vegas on his private jet. Mike Connors ("Mannix") guest stars as Hugo.
Charlie loses a woman he is dating to a young, handsome handyman, Fernando (Grammy Award-winning recording artist Enrique Iglesias), who is working on Charlie's house. Meanwhile, to Alan's consternation--and no one's surprise--Jake finds out that he must attend summer school because of his poor grades.
Jake experiences a windfall when Charlie takes him to the racetrack. Meanwhile, Alan is stuck in a hellish Department of Motor Vehicles office. Series star Jon Cryer made his directorial debut with the episode. Joel Murray ("Dharma & Greg") guest stars as Petey.
When Greg (Matt Roth), a single father from Alan's support group who has been spending a lot of time with Alan, reveals that he is gay, Charlie suspects that Greg is attracted to Alan. Alan initially refuses to believe that his friendship with Greg is anything romantic, but he soon questions his own sexuality--as does Charlie. Meanwhile, Jake is too clueless to realize that Greg's young daughter is flirting with him.
While Alan prepares Jake for Judith's wedding, Charlie continues his fling with Herb's (recurring guest star Ryan Stiles) sister, Myra (recurring guest star Judy Greer). Besides Judith's disapproval of the relationship, Charlie gets a surprise from Myra after admitting that he truly likes her.
As Judith and Herb's (recurring guest star Ryan Stiles) wedding nears, Charlie gets close to Herb's witty sister, Myra (recurring guest star Judy Greer - "Arrested Development"). But Charlie's flirtation does not please Judith, who orders Alan to make Charlie stop pursuing Myra.
When Jake starts covering his walls with posters of sexy women, Alan realizes that his son is almost grown up. He makes a last-minute attempt at father-son bonding, wanting to make the most of what little childhood Jake has left. Meanwhile, Kandi embarks on a new career as an actress.