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• Charlie Sheen
• Jon Cryer
• Angus T. Jones
• Marin Hinkle
• Conchata Ferrell
• April Bowlby
• Holland Taylor

Clips show that, moments after Alan and Kandi wed, Alan won $500,000 on a slot machine. Four months later, Charlie has returned to his bachelor lifestyle after Alan moved out of the house. Alan returns to tell Charlie that Kandi has divorced him and taken all his money, and he suffered a breakdown, and now wants Charlie to take him in again. All this surprised no one, and everyone had bets on how long the marriage would last, which Judith won. Charlie resorts to desperate measures to help his brother: he calls in their mom to talk to Alan.

Charlie finally tells Alan that he didn't marry Mia because she wanted Alan and Jake to move out of the house, but Alan finds a hole in his logic. Charlie and Alan deal with a noisy neighbor who constantly sings all the time, who happens to be Steven Tyler.

Note: For this episode, Charlie Sheen was nominated for the 2007 Primetime Emmy Award for Outstanding Lead Actor in a Comedy Series.

Charlie tries to surf to impress Dottie, a beautiful woman he just met, but after he nearly drowns he is convinced that he saw a vision of his late father, who tells him something Charlie finds worrying and crazy: he must take care of his mother.

Note: For this episode, Holland Taylor was nominated for the 2007 Primetime Emmy Award for Outstanding Supporting Actress in a Comedy Series.

Alan tries to hire his ex-wife's lawyer to help him win custody over the dog he and Kandi shared, but has to resort to desperate measures when Judith refers Kandi to the attorney she used when divorcing Alan.

Alan is overjoyed by the prospect of Judith remarrying, as he would no longer have to pay alimony. Alan gets Charlie to help him when it looks like the marriage may be derailed due to Jake's dislike of his mother's fiancé, his doctor, Herb Melnick (Ryan Stiles).

Charlie is dating a new woman, Lydia (Katherine LaNasa); her attitude is exactly like his mother's. After introducing her to Berta, Alan and Jake, they can all see it, but Charlie still cannot; Lydia and Berta do not get on well with each other.

Berta's daughter, Naomi (Sara Rue), is pregnant and Berta drags Charlie with her when she confronts the baby's father, Ronald Wienermier, in a rough neighborhood. Alan reveals his pregnancy fetish when he gets to spend time with Naomi. After having the baby, Naomi reveals that Ronald isn't the father.

Note: For this episode, Jon Cryer was nominated for the 2007 Primetime Emmy Award for Outstanding Supporting Actor in a Comedy Series, while Conchata Ferrell was nominated for Outstanding Supporting Actress in a Comedy Series.

Alan suffers from insomnia. He visits Dr. Freeman, who reveals that the cause of Alan's sleepless nights is his jealousy towards Charlie, and his inability to glide through life. Charlie hooks up with the mother of a girl Jake likes after promising not to, and Jake gets revenge on him by sliming him, and getting him arrested when Charlie tries to chase him through the beach. This causes Alan's insomnia to be cured.

Charlie gets tired of Alan's mooching and reaches the breaking point during the brothers' double date; but it works out for the best (for Charlie, anyway) when he discovers Alan's secret $5,000 hoard of money; Jake is left home alone for the first time but a horror film means it's Rose to the rescue.

Lydia's rude attitude towards Berta has them at odds and Charlie facing a dilemma: they give him a choice between each other. Meanwhile, Kandi does everything she can to stop Alan from selling their condo, seducing him every time he gets on the subject.

Charlie's friends and family put a crimp in his plan for a romantic Christmas Eve date. Evelyn sees who the date is, she takes extreme measures to prevent them from having sex, but Charlie begins to have sex with her anyway—until he learns that she might be his sister. Alan has to mediate when Herb's interest in Kandi's breasts makes Judith angry. Also, Jake gets into egg nog, making him inebriated.

Berta discovers that Alan has been dating her daughter Naomi, but welcomes him into the family, which would be great except Alan wants to stop dating Naomi, but doesn't want to break his new relationship with Berta. Also, Alan gets a piercing on 'the gay ear', which infects, causing him a problem.

Jake shares that he has heard his mother having sex with her fiancé, Herb (Ryan Stiles). This revelation brings up a repressed memory for Charlie, which leads him to seek help from Rose, and Alan having a very awkward conversation with Herb and Judith.

Charlie sets Alan up with their new neighbor, Danielle (Brooke Shields) in hopes a romance between the two will lead Alan to move out. Berta is cynical of Charlie's plans, but they later go off the rails when Charlie discovers that Danielle is a sex freak and a booze addict, and decides he wants to sleep with her instead. In the end, Danielle decides she wants to sleep with both Charlie AND Alan, shocking Alan and turning Charlie off.

Rose is moving to London, and Charlie is surprised by his reaction to the news. He soon realizes he let the best woman in his life get away from him. Meanwhile, Alan's false online dating profile leads him to a woman (Allison Janney) with a lot of bad marriages in her past.

Charlie's young, hot girlfriend takes him to a new club. She invites Alan to meet one of her friends but the men are shocked to learn that they are considered "old". A health scare has Charlie feeling depressed, but Alan has a brilliant idea to cheer him up.

After Evelyn tells Alan and Charlie how she feels about there being no mourners at her friend's funeral, the boys share their feelings that this could also be the case at hers. Evelyn tries to prove them wrong by introducing them to a couple she helped adopt a boy from China and pushing them out of the picture, literally.

Alan tries to bond with Jake when he realizes that his son's childhood is almost over, and takes him to go camping, which ends badly. Kandi pursues a career in acting and Alan supports her, but this could be derailed after Alan admits the desire to have another child.

Alan is overjoyed at the prospect of giving Judith her last alimony check. Charlie decides to go along for the ride and meets Herb's sister Myra (Judy Greer). Charlie and Myra bond over a common problem: their great hatred for Judith.

First appearance of: Judy Greer as Myra Melnick. She would later portray Bridget Schmidt, Walden's estranged wife in season 9.

Judith's and Herb's wedding is taking place soon, and Alan is looking forward to it; Charlie and Herb's sister, Myra, continue their relationship, much to Alan and Judith's dismay; Alan meets a female at Judith's wedding, who is Herb's ex-fiancée and wants to have sex with Alan. When he tries to slow things down, she creates a scene by yelling voices of pretending to having sex with him. Also, Jake repeatedly gets his tuxedo dirty.

Alan and Charlie re-examine their sexual identities after Alan befriends Greg (a gay man, played by Matt Roth) from a support group that he has been going to, and everyone thinks he is dating Greg and "coming out of the closet". Meanwhile, Jake has a crush on Greg's daughter, but doesn't know how to appeal on his new love.

Alan asks Charlie to help Jake with his book report so he can take the time to go to the DMV. Charlie agrees and then decides to take Jake down to the race track, where Jake wins $1,100. Alan is conned at the DMV, and so is Jake when he is swindled of all of his track winnings, thus learning an important lesson about money.

After the deck is damaged (Charlie sat on it and it fell off with him), Alan hires a handyman, Fernando (Enrique Iglesias). While working on the house, Fernando beats Charlie out for his girlfriend Chloe's affections, and also from Berta and Judith. Charlie fires Fernando, sleeps with Chloe in celebration, and falls off the deck again.

Evelyn gets a new boyfriend, Teddy (Robert Wagner), who bonds with Alan and Charlie by taking them to Las Vegas. The boys confront their feelings about their mother dating and men coming in and out of their lives. They decide Teddy is awesome.

First appearance of: Teddy Leopold

• Charlie Harper
• Alan Harper
• Walden Schmidt

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• "Fish in a Drawer"
• "That Darn Priest"
• "Nice to Meet You, Walden Schmidt"
• "People Who Love Peepholes"
• "Nangnangnangnang"
• "Of Course He's Dead"