Charlie Sheen and Jon Cryer star in this Emmy?-nominated comedy about two brothers and a precocious kid. Charlie Harper is a bachelor in paradise - complete with Malibu beach house, overpaid job and an incredibly active dating life.
Commercial jingle writer Charlie Harper (series star CHARLIE SHEEN) is a wealthy bachelor with a house at the beach, a Jaguar in the garage and an easy way with women. But his Malibu lifestyle is interrupted when his uptight chiropractor brother, Alan (series star JON CRYER), arrives unexpectedly with Alan's 10-year-old son, Jake (series star ANGUS T. JONES).
Unsure how to properly discipline Jake, Charlie ignores him after the child "forgets" to stop feeding the seagulls and leaves the door open. As a result, the gaggle of birds enters the house. Meanwhile, Alan gets a surprise from Judith when he goes home to fix her sprinklers.
When Alan's attempt to provide Jake with a fun-filled father/son weekend backfires, Charlie tries to console his brother by taking him to a local bar and getting Alan totally inebriated. As Alan and Charlie travel home, their meddling Cab Driver (DARRYL SIVAD), hearing the brothers' woes about their narcissistic, controlling mother, offers them some unsolicited therapy.
Charlie's longtime cleaning lady, Berta (recurring guest star CONCHATA FERRELL), quits her job, and Charlie quickly realizes he can't function without her.
After a drunken night in Las Vegas, Charlie reluctantly attends one of Jake's soccer games. But Alan and Charlie soon discover the advantages of going to these matches. The players' mothers are quite attractive, and Charlie makes a date with a particularly sexy soccer mom. Meanwhile, when two single mothers discover that Alan is newly available, they "hit" on him--literally.
Charlie rethinks the way he treats women when he, Alan and Jake are forced to cheer up a pitiful Evelyn after her serious new boyfriend terminates their relationship. Meanwhile, Charlie teaches Jake some valuable lessons about screening calls from women, but the lesson backfires when Jake reveals a little too much about what he's learned to a disapproving Alan.
Charlie's beautiful friend Cindy (KRISTIN DATTILO) frequently showers at Charlie's house after surfing. When Jake sees a butterfly tattoo on Cindy's partially nude behind and later draws a picture of it in his classroom, Judith gets angry and goes to talk with Alan and Charlie about letting her son see half naked women.
When Alan and Judith argue during a rehearsal of a play that Jake and his classmates are rehearsing, Charlie is forced to handle a roomful of fourth graders alone. The kids think Charlie is a loser until they realize he wrote the "Maple Loops" cereal jingle.
Charlie likes his sweet new girlfriend, Wendy (MYNDY CRIST), but he becomes concerned when Jake forms a strong friendship with her. When Wendy charms Evelyn as well, Charlie worries that Wendy is expecting more from the relationship than he is and ends it. But when Jake gets mad at him, Charlie learns an important lesson.
When Charlie finds out that his favorite former girlfriend, Lisa (DENISE RICHARDS - "Scary Movie 3," "Undercover Brother"), is getting married, he desperately tries to prove to her that he has become a better family man than her fiance, despite his inability to commit to her.
Charlie and Jake convince Alan to get a makeover when it appears Judith is moving forward since the breakup, sporting a new hairdo and new date. Alan realizes he may truly be in need of a change when his own son tells him he doesn't look cool.
When Charlie's cleaning woman, Berta (recurring guest star CONCHATA FERRELL), brings her sexy and rebellious 16-year-old daughter, Prudence (MEGAN FOX), to Charlie's house, Jake develops a childish infatuation with her--and Charlie and Alan try to restrain their interest in the flirtatious minor as well.
Alan worries that Charlie will become infected with Jake's contagious cold; however, Alan gets sick instead. Jake heals, and Charlie is fine. Desperate to get a date with a sexy woman, Charlie volunteers a very reluctant Alan to escort the woman's sister, turning the date into a foursome.
When Charlie learns that his credit rating is ruined, and his debts are all overdue, he discovers that his accountant, Stan (RICHARD LEWIS), is completely inept. At Alan's urging, Charlie tries to reduce his spending habits, but he has a difficult time giving up his luxuries.
Charlie and Alan find Frankie (recurring guest star JENNA ELFMAN - "Dharma & Greg," "Looney Tunes: Back in Action"), a sexy but seemingly crazy woman, hitting a car with a baseball bat. Despite Alan's warnings, Charlie becomes totally infatuated with her.
Frankie (recurring guest star JENNA ELFMAN), the beautiful and intriguing lady whom Charlie and Alan brought home after finding her bashing her therapist's car with a baseball bat, explains why she's in hiding with her 8-year-old daughter, Joanie (recurring guest star JULIETTE GOGLIA).
Alan offends Charlie by choosing their crazy cousins as Jake's guardians if he and Judith were to die. Later, Alan does some errands and leaves Jake with Charlie, who's still sulking over Alan's will. As the two play basketball, Jake falls, hitting his head.
Charlie agrees to meet with a former girlfriend who ended their relationship years earlier, leaving Charlie devastated. But Charlie's in for a huge surprise when he discovers that she is now a he, and he, Bill (CHRIS O'DONNELL - "Batman & Robin"), wants to be Charlie's friend. Initially disturbed by the sex change revelation, Charlie relents and befriends Bill.
Judith's sinister-but-sexy sister, Liz (TERI HATCHER - "Lois & Clark: The New Adventures of Superman," "Tomorrow Never Dies"), plans to attend Jake's 11th birthday party. Alan asks Charlie--who had sex with Liz in the coatroom at Judith and Alan's wedding--to behave. But when Liz arrives, she ignores Charlie and flirts with Alan instead.
Jake becomes a brooding musician when he continuously plays "Smoke on the Water" on his guitar with an ever-present grumpy attitude. In order to cheer him up, Alan tries a father/son chat, Charlie offers a jam session and Berta (recurring guest star CONCHATA FERRELL) just thinks the kid is constipated.
Alan takes Charlie to meet with his sexy and determined divorce attorney, Laura (HEATHER LOCKLEAR - "Spin City," "Melrose Place"), after Judith expresses concern that Charlie is a bad influence on Jake. Charlie and Laura begin a sexual relationship.
Alan succumbs to Judith's demand that they take Jake to therapy every week because "it's what all the other divorced parents are doing," but he doesn't realize that he, too, is having issues ... with sleepwalking. Evelyn hints to Charlie that Alan used to sleepwalk as a child, leading Charlie to come up with a clever new solution to Alan's recurring problem.
When Jake imitates one of Charlie's sexist remarks in front of Judith's support group, the women decide that Charlie's home is an unfit environment for the child. With the women's approval, Judith agrees to let Alan see Jake on weekends, but not at Charlie's place. Charlie must cajole the support group in order to win his nephew back.
One of Charlie's many women fears she's pregnant, and Charlie is relieved when the lady finds out she's not. When Alan realizes that this is not Charlie's first pregnancy scare, he suggests a permanent solution for Charlie--a vasectomy. Charlie's doctor recommends freezing some sperm in case Charlie changes his mind about having children, but things don't go quite as planned.