Charlie Sheen and Jon Cryer star along with young Angus T. Jones as three males from two generations, each learning what it really means to be a man. Charlie is a well-to-do bachelor with a house at the beach, a Jaguar in the garage and an easy way with women.
His casual Malibu lifestyle is interrupted when his tightly wound brother, Alan, who's facing a divorce, and Alan's son, Jake, come to stay with him. Together, these two and a half men confront the challenges of growing up - finally. Complicating matters are the brothers' self-obsessed, controlling mother, Evelyn (Holland Taylor), and Alan's estranged wife, Judith (Marin Hinkle).
01 - Pilot
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). Alan's wife, Judith (series star MARIN HINKLE), suspecting that she may be gay, wants a divorce.
Charlie reluctantly allows Alan and Jake to live with him temporarily, but as it becomes increasingly obvious that Judith is never going to relent, Charlie and Alan's self-obsessed, controlling unmarried mother, Evelyn (series star HOLLAND TAYLOR), offers to let father and son live with her. However, by that time, Charlie has formed a close bond with the clever Jake, even learning a few things about poker from the boy. Charlie also finds out that pretending to be a single dad with a cute kid can be a great lure for women.
Meanwhile, Charlie tries to evade Rose (series star MELANIE LYNSKEY), an attractive, offbeat neighbor who had a brief fling with him and remains determined to stay in his life by whatever means necessary.
Missing Jake, Charlie surprises even himself and asks Alan and Jake to live with him permanently. Despite their strained relationship, the brothers discover that they have one thing in common: They both love Jake and want what's best for him. Together these two-and-a-half men face the challenges of growing up.
02 - Big Flappy Bastards
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.
03 - Go East on Sunset Until You Reach the Gates of Hell
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.
04 - If I Can't Write My Chocolate Song, I'm Going to Take a Nap
Charlie's longtime cleaning lady, Berta (recurring guest star CONCHATA FERRELL), quits her job, and Charlie quickly realizes he can't function without her. When Alan tries to take Berta's place but doesn't succeed, Charlie sends him to lure her back. Meanwhile, Alan places Charlie in charge of getting Jake ready for Judith, who is coming to take her son out for a nice dinner with her parents. Rock star STEVEN TYLER of the band Aerosmith does a voice-over as himself.
05 - Last Thing You Want is to Wind Up with a Hump
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.
06 - Did You Check with the Captain of the Flying Monkeys?
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.
07 - If They Do Go Either Way They're Usually Fake
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. To Alan's surprise, Judith and Cindy become friends. When Cindy teaches Judith how to surf, Alan wrongly suspects that the two women are sexually involved and confronts his estranged wife, who does not appreciate his assumptions. Meanwhile, Alan and Judith are both upset when Charlie teaches Jake about distinguishing women's fake implants from real breasts.
08 - Twenty-Five Little Pre-Pubers Without a Snoot-Ful
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. When Charlie discovers the children know every jingle he's ever written, he decides to use his commercial expertise to craft the play - with some interesting results.
09 - Phase One, Complete
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. Meanwhile, Alan takes playing his board game very seriously when competing against Rose.
10 - Merry Thanksgiving
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 fiancé, despite his inability to commit to her. He persuades Judith to bring her parents and Jake to his house for a big family Thanksgiving dinner, along with Alan, Evelyn, Rose and Charlie's irritable housekeeper, Berta (recurring guest star CONCHATA FERRELL). But with that bunch, Charlie can only carry on the charade for so long.
11 - Alan Harper, Frontier Chiropractor
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. But when Charlie takes Alan shopping, the brothers clash over what image is right for him. Meanwhile, highfalutin Evelyn remains at Charlie's house to bond with her grandson, Jake.
12 - Camel Filters and Pheremones
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. Meanwhile, Rose's dream comes true when Charlie pretends that Rose is his girlfriend in order to fend off Prudence. And Judith fears that the guys' lifestyle is unacceptable for Jake.
13 - Sarah Like Puny Alan
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. Charlie tries to speed Alan's recuperation, but when Charlie gets ill and Alan discovers how attractive the sister is, their roles reverse. Meanwhile, Alan objects when Charlie takes advantage of having the same tastes in humor as his 10-year-old nephew.
14 - I Can't Afford Hyenas
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. After the thought of borrowing from Evelyn becomes too much to bear, Charlie accepts help from an unlikely source. Meanwhile, Charlie teaches Jake the finer points of sports gambling - to Alan's consternation.
15 - Round One to the Hot Crazy Chick
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. After they make a quick getaway from the parking garage where Alan accidentally set off the smashed car's alarm system, Charlie brings Frankie back to his Malibu home. Alan, wary of her at first, reconsiders when she compliments his career as a chiropractor. But the two brothers, both competing for her attention, are taken aback by a secret that she's been hiding.
16 - That Was Saliva, Alan
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). Both of the men are romantically interested in Frankie, and she reciprocates with one of the brothers. And Joanie likes Jake, who is completely disinterested in her.
17 - Ate the Hamburgers, Wearing the Hats
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 rushes him to the emergency room and finds that his charm with women doesn't work with the admitting nurse. Charlie knows the stakes are high, as he must prove to Alan that he can be a responsible guardian.
18 - An Old Flame With a New Wick
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. But Charlie and Alan are horrified when Bill starts dating their mother, and Evelyn becomes sexually intimate with Charlie's ex-girlfriend!
19 - I Remember The Coat Room, I Just Don't Remember You
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. Liz proceeds to cause a commotion between her sister, whom she's never really gotten along with, and her ex-brother-in-law. Meanwhile, Evelyn forgets that it's cake, not alcohol, that's traditionally served at a child's birthday party, and she proceeds to party her own way.
20 - Hey, I Can Pee Outside in the Dark
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. Finally, Judith convinces Alan that Jake needs professional assistance, and they enlist the help of Dr. Linda Freeman (recurring guest star JANE LYNCH - "Best in Show").
21 - No Sniffing, No Wowing
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. Laura doesn't care that he dates other women, but she does have one request: Charlie must be available for her whenever she wants him. Charlie loves the idea - until Laura takes advantage of the situation. But when Charlie tries to get out of the arrangement, Alan suffers.
22 - My Doctor Has a Cow Puppet
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. Recurring guest star JANE LYNCH ("Best In Show") returns as Jake's therapist, Dr. Linda Freeman.
23 - Just Like Buffalo
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.
24 - Can You Feel My Finger?
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.