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24 Episodes 2004 - 2005
The sitcom, already established as a crowd-pleaser in its first season, runs even faster the second season and takes off with a sprint in an opener that boasts a dream guest cast of Sean Penn, Elvis Costello and Harry Dean Stanton\, playing themselves, as friends of Charlie (Charlie Sheen) who meet occasionally for therapy disguised as male bonding. Alan (Jon Cryer) feels left out, realizing he and Charlie are brothers, but not friends. Apparently, that gulf formed very early: In one of the season's memorable episodes, Charlie confesses it was he who planted the stolen toy that Alan was accused of shoplifting when they were boys, an event that left Alan worrying all his life that he may have a latent dark side. He could use the edginess, as the season further underscores his blandness just as it goes even further to play up Charlie's hedonistic and shameless ways with women. During the funeral for a man once married to Evelyn (Holland Taylor), Charlie's mind is on the young grieving widow. Alan does have his effervescent moments, though, never more so than when he pretends to be Charlie's lover as a favor to Charlie, who hopes to impress a gay ad-agency exec. If Alan shines brightly, for a moment, anyway, it also becomes apparent that Jake is not the brightest bulb as Berta (Conchata Ferrell) complains about his slacker habits and a teacher is angered when he gives her the finger. In other developments, Alan begins to bond with Rose (Melanie Lynskey), whose unwanted visits become more frequent, and Judith (Marin Hinkle) begins dating Jake's pediatrician (Ryan Stiles). Other memorable guest appearances include Orson Bean, Jeri Ryan and Camryn Manheim.
Episode 1
Mon, Sep 20, 2004 30 mins
Sean Penn, Elvis Costello and Harry Dean Stanton appear as themselves in the second-season opener in which Alan is hurt that Charlie excludes him from his regular meeting with his friends, which he refuses to call "a support group".
Episode 2
Mon, Sep 27, 2004 30 mins
Alan is shocked to learn that Jake's pediatrician is sleeping with Judith; while Evelyn confronts Charlie about his hatred for her and is joined by Berta and Rose who demand to know as well.
Episode 3
Mon, Oct 4, 2004 30 mins
Jake could be suspended for making an obscene gesture at school, but Charlie thinks he has a way to fix things with the teacher in order to keep her from punishing the boy.
Episode 4
Mon, Oct 11, 2004 30 mins
Charlie trades cars with his mother so that she can impress a client with his Mercedes, but later regrets his decision when he learns how she used his vehicle; Alan is bothered that Jake seems to like Judith's new boyfriend more than him just because the man has a boat and a pool.
Episode 5
Mon, Oct 18, 2004 30 mins
Charlie meets his match in a self-centred woman who takes control of the relationship and treats him the same way he usually treats his dates.
Episode 6
Mon, Oct 25, 2004 30 mins
A guilt-riddled Charlie confesses he did something to Alan when they were kids that has affected Alan's life negatively.
Episode 7
Mon, Nov 8, 2004 30 mins
Charlie and Alan hire Berta's disturbed sister as a caterer after Evelyn guilts them into throwing a party for her.
Episode 8
Mon, Nov 15, 2004 30 mins
In a strange reversal for the brothers, Alan meets a woman at the supermarket who releases his uninhibited wild side.
Episode 9
Mon, Nov 22, 2004 30 mins
Charlie's old flame Lisa returns. She's no longer married, but has a child for whom Charlie feigns interest in order to win over Lisa.
Episode 10
Mon, Nov 29, 2004 30 mins
Alan and Rose begin a surprisingly close friendship that could become something more. Meanwhile, Charlie tries to compose a theme song for a cartoon based on a comic book.
Episode 11
Mon, Dec 13, 2004 30 mins
Charlie learns that there is a website devoted to trashing him and his womanising ways. Meanwhile, Alan mistakenly thinks Judith wants to get back together with him.
Episode 12
Mon, Jan 3, 2005 30 mins
A high-school friend visits Alan, who is awed by how beautiful she's become; and the transformation doesn't escape Charlie's notice either.
Episode 13
Mon, Jan 17, 2005 30 mins
When a water pipe breaks in Judith's home, flooding the house, Alan invites her to stay at Charlie's until the repairs are finished, but when she goes on a date while staying there, he regrets his kindness.
Episode 14
Mon, Jan 31, 2005 30 mins
Evelyn pushes Alan too far when she crushes Jake's self-esteem, and he tells her she's no longer allowed to see her grandson.
Episode 15
Mon, Feb 7, 2005 30 mins
Worried over getting a colonoscopy, Alan takes Charlie's advice to go with him to Las Vegas and to bring Jake. But obstacles keep delaying the outing, including Jake getting sick.
Episode 16
Mon, Feb 14, 2005 30 mins
Judith goes to Hawaii, leaving Jake with Alan and Charlie for an entire week, and everything that can go wrong does for all three...er...two and a half men.
Episode 17
Mon, Feb 21, 2005 30 mins
A wild night of pleasure leaves Charlie in severe back pain, but it's not enough to keep him from hitting on his beautiful doctor which appalls Alan.
Episode 18
Mon, Mar 7, 2005 30 mins
Charlie persuades Alan to pretend they're a couple to impress a gay ad-agency exec, then has a dilemma when he falls for the man's gorgeous ex-wife.
Episode 19
Mon, Mar 21, 2005 30 mins
A bold Alan asks out Sherri, who was indifferent to Charlie when they dated, and, to everyone's surprise, she's attracted to Alan.
Episode 20
Mon, Apr 18, 2005 30 mins
When Charlie and Alan antagonise each other like adolescent boys, Rose gets them to sit down and discuss their unresolved issues.
Episode 21
Mon, May 2, 2005 30 mins
Alan, Jake and a reluctant Charlie accompany Evelyn to the funeral of one of her ex-husbands, and Charlie starts hitting on the young and beautiful widow.
Episode 22
Mon, May 9, 2005 30 mins
Alan foolishly borrows money from Evelyn to buy a Porsche, and in turn she asks him to go on a blind date with the daughter of a man she's dating.
Episode 23
Mon, May 16, 2005 30 mins
A women's volleyball team walks into a bar. It's no joke, but a godsend for Alan and Charlie, who are drinking away the guilt of letting Jake stay with Evelyn.
Episode 24
Mon, May 23, 2005 30 mins
In the second-season finale, told through flashbacks as Jake reads a report to his class, an angry husband confronts Charlie for sleeping with his wife.