It’s perfectly natural for comedy shows to have a premiere season that doesn’t quite reach its full potential while the series spends the first season getting into a comfortable groove – Two and a Half Men was not one of these shows.
Right from the beginning, the simple premise of a well-off brother taking in his hapless younger brother as well as his nephew gave audiences a hilarious half-hour of television to look forward to every Monday night on CBS.
10 Ate the Hamburgers Wearing the Hats, Episode 17 (8.1)
One of the key staples of the series was that Alan (despite being vastly less successful in life than his brother) never sees Charlie as a mature adult. During this episode that fact became crystal clear when Alan informed Charlie that he wasn’t the person next in line to get Jake should he die. This understandably hurts Charlie’s feelings and he sulks and pouts about it, but he ends up getting to prove himself as a guardian when Jake needs to get taken to the hospital and Charlie successfully handles the situation.
9 Merry Thanksgiving, Episode 10 (8.2)
During this Thanksgiving special, Charlie finds out that an ex-girlfriend whom he thought could be the one is getting married to another guy – so naturally, Charlie invites her to Thanksgiving dinner in order to try and win her back by proving he can be a family man. He recruits his brother, nephew, mother, maid, and a few other random-distant-not-really-related relatives to fill in seats and does his best to play the part of a generous host. But (predictably) the evening turns into a mess resulting in the woman turning down an impromptu proposal from Charlie.
8 No Sniffing No Wowing, Episode 21 (8.2)
It can often be forgotten that while Alan was never able to get out of debt and sustain himself throughout the entirety of the series, the reason is because of Charlie. In this episode, Alan and Charlie meet with his divorce attorney about his case and it truly seems as though Alan is set to walk away with his fair share. That is until Charlie decides to sleep with Alan’s attorney and then dump her the day of the settlement, resulting in Alan’s lawyer taking her revenge by giving Alan’s ex-wife everything (and more).
7 I Remember the Coatroom I Just Don’t Remember You, Episode 19 (8.2)
Siblings fight and that’s only natural – what isn’t natural is a woman trying to sleep with her sister’s ex-husband just for spite, or vice versa. That’s exactly what happened in this episode when Jake’s Aunt Liz shows up at the house for his birthday party and makes it readily known that the present she wants is Alan.
She and Judith bicker back and forth, revealing a secret or two, and Judith threatens to sleep with Charlie if Alan sleeps with Liz. Neither women budge and take the men to their rooms to carry out the deed… only to have both guys chicken out and call it off.
6 Most Chicks Won’t Eat Veal, Episode 1 (8.3)
The pilot episode of the series (and a rare case where the title isn’t “Pilot”) introduced the world to Charlie Harper and his Malibu beach house. When his younger brother Alan shows up in the middle of the night after being kicked out of the house by his wife, Alan asks if he can stay for just a couple of days while things cool down with his wife. Eventually, Alan brings his 10-year-old son Jake over and Charlie, a known drunk and degenerate, puts very little effort into cleaning up his act for the adolescent. Things only get worse when Alan’s wife, Judith, reveals to Alan that she thinks she might be gay, forcing Alan and Jake to have to stay at Charlie’s a little while longer (12 years is just a little while, right?).
5 Can You Feel My Finger? Episode 24 (8.3)
The season finale of the first season got the same IMDb rating as the pilot as it found Charlie choosing to get a vasectomy after a one-night stand calls him with a pregnancy scare. The episode plays heavily on the sperm-jokes and masturbation hijinks as Charlie appears quite uncomfortable with the entire situation. Charlie finally reaches the day of his surgery and just as the doctor is about to carry out the ‘snipping’ he has to stop and cancel due to the fact that his wife goes into labor. Charlie takes this as a sign from the universe that he shouldn’t get the surgery – so he gets a date with the nurse instead.
4 If They Do Go Either Way They’re Usually Fake, Episode 7 (8.4)
One of the funniest aspects of Two and a Half Men was the fact that Charlie refused to clean up his act for his nephew and continued living his life of debauchery whenever Jake was around.
During this episode, Charlie finds himself in hot water after Jake draws a picture for a school project and chooses the butt of a woman he saw in Charlie’s kitchen as his muse. Judith reprimands Charlie for his lifestyle, but Charlie turns the tables on her and ends up comforting her and helping her solve her own personal problems.
3 An Old Flame With A New Wick, Episode 18 (8.5)
It’s hard to believe that Two and a Half Men used an entire episode to cover transgender people all the way back in 2004 and actually did it quite tastefully despite the show’s known vulgarity. This episode finds Charlie waiting for an old girlfriend at a bar only to discover that the girlfriend, Jil, has come out as trans and now goes by Bill. Charlie gets past the initial shock and accepts Bill for who he is, only to have his own mother meet Bill and decide that she wants to date him. Bill eventually reveals to Evelyn that he’s transgender and it doesn’t matter in the slightest to her… but then she finds out that Bill slept with Charlie before his transition and that turns out to be a faint-inducing deal-breaker.
2 Just Like Buffalo, Episode 23 (8.6)
Will Charlie ever learn? Spoiler alert – no. During this episode, the entire premise revolves around a few distasteful lines that Charlie says to Alan in the beginning scene about how there’s no need to get married if you already have someone who cooks and cleans for you. Jake hears the line, parrots it to his mother and her friends, and it causes the group of women to herd up on Alan and declare that Jake is no longer allowed to stay at Charlie’s house. With Alan unable to coax them into changing their minds, Charlie turns on his charm and manages to not only persuade the ladies into letting Jake stay at his house, but he ends up getting all of them to come over and drink on his deck with him.
1 Camel Filters & Pheromones, Episode 12 (8.8)
Before she became a huge movie star Megan Fox was spending her days trying to break into Hollywood – one such day was when she guest-starred on Two and a Half Men as Berta’s 16-year-old granddaughter. Her character, Prudence, shows up at the beach house to help her grandmother clean and immediately becomes a distraction to all of the males in the household, especially Jake who develops an immediate crush. The episode ends with Prudence showing up at Charlie’s house in the middle of the night with her boyfriend and asking to crash before they head to Vegas to get married in the morning. Berta shows up, breaks up the midnight-bash, and Prudence was never seen again.
