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1* ActorLeavesCharacterDies: Charlie was killed off by being pushed in front of a train after he was caught cheating on his fiancée, Rose. And just to add insult to injury, the funeral is full of one night stands and angry exes. And after he is cremated, Walden's first appearance has Alan [[AshesToCrashes spilling Charlie's ashes all over the ground.]] Then Alan vacuums Charlie's remains with a Dustbuster.
2* BillingDisplacement: Ashton Kutcher (Walden) receives top billing during the final four seasons, even though it’s Jon Cryer (Alan) who gets the most focus between the two of them. However, both actors are credited onscreen at the same time but it’s positioned in a way where it’s hard to decipher whose name comes first.
3* ContractualPurity: Not the show itself, which was always fairly raunchy, but its guest stars. In its later seasons, the show made a [[RunningGag running meta-gag]] out of casting former Creator/DisneyChannel stars like Music/HilaryDuff, Music/MileyCyrus, Creator/EmilyOsment, and Creator/AlyMichalka to play Walden, Jake, and Jenny's [[ReallyGetsAround loose]], [[LowerClassLout trashy]], [[MsFanservice scantily-clad]] girlfriends, specifically to spoof their family-friendly reputations.
4* CreatorBacklash: Angus T. Jones (who played Jake) left the show at the end of season 10 after he converted to Seventh-Day Adventism. He now treats it as an OldShame, claiming the show to be "immoral" and that he had been a "paid {{hypocrite}}" by starring on it. Though that didn't stop him from making a cameo in the series finale.
5* CreatorBreakdown: The circumstances surrounding Creator/CharlieSheen's exit are an ''explosive'' example. His marriage to Brooke Mueller fell apart and he entered a downward spiral of drinking and drug use. Then he began demanding that he be given an enormous raise (somewhere in the neighborhood of $2 million per episode) and refused to come on set until CBS agreed. As this was happening, he began making bizarre public appearances and strange social media posts. In the end, the powers that be decided that Sheen wasn't worth the aggravation, fired him, killed Charlie off, and retooled the show by bringing in Ashton Kutcher.
6* CreatorsFavorite: Creator/EmmanuelleVaugier described Mia as her favorite character to have played in her career [[https://vancouversun.com/entertainment/television/vancouver-born-emmanuelle-vaugier-relishes-wily-strong-willed-roles in an interview]].
7* TheDanza:
8** Creator/CharlieSheen as Charlie Harper.
9** Creator/PaulaMarshall as Paula, Alan’s UsefulNotes/{{Transgender}} girlfriend from ep. 9-10 of season 11.
10* DyeHard: Creator/JonCryer's hair began to thin dramatically and, while he was open about it, the hair and makeup department used a powdered hair loss concealer to make it seem he still had a full head of hair. After the series ended, he shaved his head and grew a beard.
11* FakeAmerican: Rose, played by New Zealander Creator/MelanieLynskey.
12* FollowTheLeader: Starting with Season 10, the show started to incorporate quite a small bit of the nerd-based humor that made ''Series/TheBigBangTheory'' so popular.
13* LawyerFriendlyCameo: Jenna Elfman and Thomas Gibson's cameo in Season 9 had allusions to their previous roles as Series/DharmaAndGreg, but Chuck Lorre couldn't use the characters' names or established personalities because they are owned by ABC while ''Two and a Half Men'' is a CBS production. Lorre used this fact to comfort viewers who were upset to see the two actors play characters whose marriage is on the rocks, believing that Dharma and Greg's relationship broke down since their own series ended.
14* MoneyDearBoy: A variation; the main reason why Creator/ChuckLorre pushed the network to commission a pilot was because co-creator Lee Aronsohn would cease to be eligible for WGA health coverage if one of his scripts wasn't put into production very soon. Fortunately for all concerned, it turned out that the network quite liked the pilot...
15* TheOtherDarrin: Dolores Pasternak was originally played by Missi Pyle. When she returned two years later, she was played by Creator/AliciaWitt. In brief appearances in later seasons, [[TheOriginalDarrin Missi Pyle came back]].
16* TheOtherMarty: Creator/BlytheDanner played Evelyn Harper in the original pilot, but she reportedly wanted to make changes to the character the producers didn’t like. Her scenes were reshot with Creator/HollandTaylor.
17* PlayingAgainstType: Ryan Stiles. [[Series/TheDrewCareyShow Lewis]] was a {{Jerkass}} and a borderline sociopath while Herb is one of the nicest people on the show.
18* QueerCharacterQueerActor: Evelyn Harper has had sex with both men and women. She's played by Creator/HollandTaylor, who's a lesbian in real life.
19* RealLifeRelative:
20** Creator/CharlieSheen's brother Creator/EmilioEstevez made a guest appearance. Charlie (Harper) actually tells Alan [[NoRespectGuy to his face]] that he's like the brother he never had.
21** So did their father [[Creator/MartinSheen Martin]] in another episode, as Rose's father.
22** In the episode "Yes, Monsignor", Charlie's ex-wife Creator/DeniseRichards played Charlie's recently divorced ex-girlfriend and their daughter Sam appeared as her infant daughter.
23* RecastAsARegular: Jennifer Taylor appeared in multiple guest spots as different characters before being cast as Chelsea.
24* TransCharacterCisActor:
25** Transgender man Bill from "An Old Flame With a New Wick" is played by Creator/ChrisODonnell.
26** Likewise with Paula from season eleven, who was played by Paula Marshall.
27* WhatCouldHaveBeen:
28** CBS did not want Jon Cryer to play Alan, feeling Cryer was a show killer. Chuck Lorre was impressed by Cryer’s reading, however, and brought him in to audition anyway. Lorre later said Cryer was the first person he’d ever seen change Les Moonves’ mind.
29** Creator/HughGrant was originally signed to replace Creator/CharlieSheen. His character was to be a smooth-talking ConMan who tricks Alan into letting him move in, without paying rent. Grant decided that he didn't want to commit to a multi-year contract for a television series, and backed out of the role. Creator/WoodyHarrelson, Creator/RobLowe, Creator/JeremyPiven and Creator/JohnStamos were also considered.
30** The original plan for the ending of the series, according to Creator/ChuckLorre's vanity card:
31--->"I know a lot of you might be disappointed that you didn't get to see Charlie Sheen in tonight's finale. For the record, he was offered a role. Our idea was to have him walk up to the front door in the last scene, ring the doorbell, then turn, look directly into the camera and go off on a maniacal rant about the dangers of drug abuse. He would then explain that these dangers only applied to average people. That he was far from average. He was a ninja warrior from Mars. He was invincible. And then we would drop a piano on him. We thought it was funny. He didn't. Instead, he wanted us to write a heart-warming scene that would set up his return to prime time TV in a new sitcom called The Harpers starring him and Jon Cryer. We thought that was funny too."
32* WriteWhatYouKnow: Creator/ChuckLorre has experience as a jingle writer; he wrote the theme song for ''WesternAnimation/{{Teenage Mutant Ninja Turtles|1987}}''. Overlaps with ActorAllusion (Creator Allusion?) when Charlie plays said theme song on the piano for Jake in an early episode, only for Jake to be utterly clueless about where it's from.
33* WriteWhoYouKnow: Charlie Harper's characterization is basically that of his actor, Creator/CharlieSheen. It's even referred to as such by Trifecta.
34* YouLookFamiliar:
35** The actress who plays Chelsea, one of Charlie's few meaningful relationships for a long time had already appeared in other roles in previous episodes, including the Pilot.
36** Creator/AprilBowlby, who later played Kandi, made an earlier appearance playing a woman in Charlie's shower, called "Bubbles." It is possible Bubbles ''was'' Kandi, as Kandi shows up two episodes later and acts just like her (April Bowlby is credited as "Kimber" in that episode, even though she's never addressed as such in the entire episode).
37** Creator/JennaElfman appeared in a two-part episode in the first season as a woman named Frankie. She later appeared as [[Series/DharmaAndGreg Dharma]] in the Season 9 opener.
38** Creator/JudyGreer, who plays Walden's wife appeared in the fourth season as Herb's sister, Myra.

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