Two And A Half Men: 10 Best Season 5 Episodes (According To IMDb)
It can be easy to forget that only a few shorts year before Charlie Sheen would end up derailing Two and a Half Men with his off-screen antics/comments that the CBS comedy was among the best shows on television.
By the time it reached season 5, the show earned 25 Emmy nominations along with 4 wins and it seemed as though the unlikely-hit about two brothers and their son/nephew living in a house in Malibu could do no wrong.
10 Large Birds, Spiders and Mom: Episode 1 (8.0)
In the very first episode of the season, the audience finds out that Jake actually passed summer school and was going to be moving on to Junior High.
Apparently, Alan and Charlie went to junior high in hell because the two brothers spend the rest of the episode preparing Jake for bullies, hazing, and even potential beatings from his other classmates. Jake becomes so traumatized from their rendition of what junior high will be like that he skips on his first day.
9 Media Room Slash Dungeon: Episode 2 (8.0)
One of the most common running-gags on Two and a Half Men was the constant joking that Evelyn was a terrible mother and had a horrible relationship with her kids. That's why it was such a shock when Charlie has to escort his mother to a black-tie benefit and actually ends up having a great time with her (due to her talking trash about everyone else instead of him for a change).
Meanwhile, Alan starts dating a woman who appears into him at the beginning of the date, yet has a massive meltdown after they've slept together and has to call her therapist to prevent herself from becoming completely hysterical.
8 City of Great Racks: Episode 4 (8.0)
Fans were left stunned when Two and a Half Men essentially wrote Rose out of the show in season 4 when she moved to London, but they were quickly satiated in the fourth episode of season 5 when she made her reappearance. Charlie begins to get serious with his girlfriend, Linda, but they haven't slept together yet and Charlie begins to see Rose's face on different women everywhere he goes.
When Alan and Jake insist that Rose is still in London and Charlie's just imagining things, he flies to London to see Rose in person. He arrives at her apartment and they chat before going out to get a beer... but not before the camera shows the audience an assortment of wigs in Rose's apartment that are identical to the hairstyles of the women Charlie thought were Rose back in America.
7 Shoes, Hats, Pickle Jar Lids: Episode 9 (8.1)
By this point in the series, fans had already been introduced to Teddy, Evelyn's new fiancé, but they had yet to meet Courtney, Teddy's daughter. She appears for the first time in this episode where Charlie takes an immediate shine to her, but is warned by Teddy to stay away from her.
Unfortunately, Courtney ends up calling Charlie about selling him a Bentley (she's a high-end car saleswoman) and a short-string of events leads to them in bed together. However, it turns out that Courtney was just setting Charlie up for a trap and ended up selling him a Ferrari (a twice-as-expensive car) instead.
6 Winky Dink Time: Episode 14 (8.1)
When Charlie runs into an old flame at a coffee shop (but can't remember her name) he gets himself into quite a dilemma when Jake takes a shine to the woman's daughter and sets the four of them up on a double-date.
Once out to dinner, Charlie is eventually found out and admits he doesn't know the woman's name - except that she then reveals the two of them have never slept together, prompting Charlie to proclaim "no wonder I don't remember you".
5 Kinda Like Necrophilia: Episode 10 (8.2)
Alan was never known for being able to reel-in good-looking women so it cut him deeply when he found out that Charlie stole his beautiful girlfriend from him in high school. In order to get back at his brother, Alan decides to take a shot at Charlie's current gorgeous French girlfriend and manages to actually steal her away from Charlie.
Alan eventually gets into bed with the woman and discovers that she has a major sexual flaw (lays completely still in bed, like a corpse) which causes Alan to not go through with it. Alan then realizes that he didn't actually 'steal' the woman away from Charlie and that he was trying to get rid of her all along.
4 Meander to Your Dander: Episode 11 (8.3)
For a decent part of season 5, Alan was involved with a woman named Donna and it seemed as though the two were a great fit for one another. That is until Alan divulged to Charlie that their sex life was so lackluster that they had tried everything and couldn't spice things up, prompting Alan to want to end the relationship and ask Charlie for advice on how.
Once Charlie gives Alan a step-by-step process of how to ends things, Alan arrives at Donna's house and proceeds to tell her that it's over... only for one of Donna's attractive friends to show up and reveal that Donna had planned a three-way for Alan that he would no longer be getting.
3 The Soil is Moist: Episode 13 (8.3)
Alan runs into an old friend (a woman) from the days of his marriage who happens to still be friends with Judith and ends up getting into a relationship with her. The woman tells Alan that he's a fantastic lover and Alan starts to feel pretty good about himself - until the woman informs him that Herb (Judith's new husband) is apparently the best lover that Judith has ever had.
Alan immediately spirals out of control trying to figure out what Herb's secret is but comes up empty. At the end of the episode, it's revealed that Herb has a 'special skill' that he uses for gardening that also helps him pleasure Judith.
2 Is There a Mrs. Waffles?: Episode 8 (8.6)
It was common knowledge that Charlie obtained his wealth from writing jingles, but nobody could have expected that the writers would decide to turn Charlie Harper into a children's singing star when his money started to run out.
Under the pseudonym 'Charlie Waffles' Charlie sings and entertains scores of children with his immature songs, but runs into a problem when he gets booked for a concert and divulges that he has stage fright. Contractually obligated to perform the concert, a nervous Charlie gets hammered beforehand and does the event completely wasted - which the kids end up loving.
1 Fish in a Drawer: Episode 17 (8.8)
What a spoof. What a plot twist. What an episode! When Evelyn and Teddy get married at the beach house, it immediately turns into a crime scene (a spoof of CSI) when Teddy turns up dead in Charlie's bed with his pants around his ankles.
The entire family gets questioned and interrogated and none of them seem to have any clear motives... until it's shockingly revealed that Courtney's actual name is Sylvia Fishman (Teddy's was Nathan Krunk) and that the two of them were "scam artists" who traveled the country stealing money from people in an assortment of different ways. It's also revealed that Teddy wasn't killed, but rather died from a heart-attack. A lot of hilarious content to process there.