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1* BrokenBase: Should Will and Jack have got together (and now, should they get together in the reboot)? Some see them as meant for each other, and that it would be the perfect, inevitable culmination of seasons worth of teasing. Others hate the idea because they love that the show has two gay leads who have a platonic relationship (a rare occurrence), demonstrating that gay men are capable of being just friends with each other. The debate has very little in-between.
2** Believe it or not the show was quite controversial within the gay community when it first aired, many considering Jack too much of a camp stereotype and others thinking Will was played too straight. Eventually it won both sides over.
3* CrackPairing: A very large portion of fanfiction writers ship Will/Karen.
4* CrazyIsCool: Karen is an alcohol and drug-addicted CloudCuckoolander and the fans love her for it.
5* CrossesTheLineTwice:
6** "I Do. Oh, No, You Di-in't" has Karen introduced to Marion, the brother of her soon-to-be-husband Lyle Finster. The first thing Marion does after barely exchanging two lines of dialogue with Karen is kiss her right in front of his brother and then ''[[SiblingIncest kiss his brother]]''. And then:
7--> '''Karen''': Boy. Your brother sure can kiss.
8--> '''Lyle''': That's nothing. Wait 'til you meet my dad.
9** "Rosario's Quinceañera", which also features a member of the Finster family, arguably outdoes the above. It is mentioned that Karen had a threesome with [[SitcomArchNemesis Lorraine Finster]] and Ly the latter's father. To top it all off, this information is revealed during Rosario's funeral.
10** Karen's treatment of her house staff in general would qualify, especially with the way she often laughs at poor Smitty's misfortunes.
11** In "Anchor Away", Karen refers to her divorce lawyer as Ju, which Grace takes offense at as she thinks Karen is calling him "Jew". Karen "corrects" Grace by saying that the lawyer is Chinese-American and that Ju is his name only for the lawyer to state that his name is Joe and he is ''Korean''-American.
12* EnsembleDarkhorse: Snarker supreme Rosario is also popular with many fans, primarily because of her funny interactions with Karen.
13* FairForItsDay:
14** Offensive as it may have sometimes seemed, by the time it ended, it was one of the first American shows with a gay man as a central character, and remains one of few not relegated to cable at midnight.
15** Additionally, the show's original run happened right during the tipping point of cultural acceptance of homosexuality. As such, it started out as a landmark step forward to have two gay leads on a popular network show in prime time. However, as homosexuality became more socially acceptable and more serious material was made, the show seemed less fresh and daring.
16** One interview with the creators indicates that they were fully aware that they were at a tipping point in social attitudes and were trying to play a delicate balancing act. Essentially they knew that they couldn't have a StraightGay character like Will without part of the audience saying "That's not what ''real'' gay people are like!" and they couldn't have a CampGay character like Jack without the other part of the audience saying the same thing. So they put both in there and hoped they balanced out. The fact that Will became a bit more camp over time was most likely due to RuleOfFunny, but also possibly the fact that Jack started getting episodes that took his feelings and emotions seriously too... they were still in balance.
17* FanPreferredCouple: While Karen ends the show getting back together with her husband Stan, most fanfiction for the show instead pairs Karen with her boss Grace. This is mainly due to the chemistry between the two and the massive amounts of LesYay between them, as well as the fact that Stan is TheGhost. It also easily overshadows Grace with any of her canon love interests, such as her marriage to Leo. On Platform/ArchiveOfOurOwn and Platform/FanfictionDotNet, the Grace/Karen pairing makes up most of the shipping fanfiction for the show.
18* FridgeHorror: In "Fagmalion Part One: Gay It Forward", Grace is confused about whether or not she was inappropriately groped by her neighbor Julie while the latter was giving her a massage. The season 10 episode "Grace's Secret" reveals that [[spoiler:Grace was sexually assaulted by her father's friend Harry when she was 15. This is horrific enough by itself, but it adds another layer to Grace's panic and confusion in "Gay It Forward" as she was likely bringing back memories of what Harry did to her. Considering that people who were sexually abused as children or teenagers may take years to come to terms with their trauma, the incident with Julie may have also played a factor in why Grace finally felt bold enough to tell her father about Harry.]]
19* HarsherInHindsight:
20** A Season 8 episode has Will ask, "Where in the world are Matt Lauer's manners?". In 2017, Matt Lauer was one of the many figures in the entertainment business accused of sexual misconduct.
21** The RunningGag about Grace's [[BigEater big appetite]] feels less amusing after Debra Messing [[https://www.dailymail.co.uk/tvshowbiz/article-8605179/Debra-Messing-admits-way-skinny-Grace.html revealed she felt pressured to lose weight during the show's original run.]]
22*** Adding to the above, the Grace and Jack's b-plot in "The Scales of Justice" deals with them trying to lose weight which also has some RealitySubtext.
23** In Season 3, Karen mistakenly believes that Stan is cheating on her. In Season 5, he does have an affair for real.
24** In Season 5, Creator/GeneWilder appears in several episodes as Mr. Stein, one of the head partners of Will's law firm. Stein's introductory episode depicts him as extremely absentminded and suffering from short-term memory loss, routinely needing to be reminded of his identity and surroundings. Will later finds him having a breakdown in the men's room where Stein admits that he's been absent from the firm because he was in a mental hospital; he claimed he was working in the firm's London office in order to protect his professional reputation. After Wilder's death in 2016, his family revealed that [[https://www.forbes.com/sites/nextavenue/2016/08/31/gene-wilder-and-his-alzheimers-secret/#383b58e247e3 he was suffering from Alzheimer's]], and that he'd kept his illness a secret to avoid upsetting and disappointing young fans of ''Film/WillyWonkaAndTheChocolateFactory''.
25** The series plays Grace's insecurity regarding her relationship with Leo for laughs several times, from her being jealous when she meets his ex-girlfriend Diane to fearing he will cheat on her. These jokes become less funny when the season 6 finale reveals he cheated on her while they were in Cambodia.
26** Any friendship scene between Grace and Karen is harder to watch now, given the HostilityOnTheSet between Debra Messing and Megan Mullally during the revival's final season.
27** In "Von Trapped," Grace meets a group of children at a sing-a-long showing of ''Film/TheSoundOfMusic'' and, after learning none of the children had ever seen the movie before, dramatically asks "What kind of parents do you have?" leading the eldest girl to retort [[ArmorPiercingResponse "Well, they left me here with you!"]] Said girl was played by Creator/JennetteMcCurdy, who would reveal in her 2022 memoir that her StageMom mother Debra was far worse in real life, to the extent she titled the memoir ''I'm Glad My Mom Died.''
28* HilariousInHindsight:
29** Creator/NeilPatrickHarris had a guest role in Season 2 as a gay man who had been converted to heterosexuality. Six years later, Harris came out as gay.
30** Creator/VictorGarber also had a guest appearance on the show before he came out.
31** Eric Allan Kramer guest starred in a Season 7 episode where Leigh-Allyn Baker's character also appeared. The two would later co-star in ''Series/GoodLuckCharlie''.
32** Reed Alexander appeared in the episode "A Little Christmas Queer". The very next episode, "Von Trapped", had fellow ''Series/{{iCarly}}'' alumnus Creator/JennetteMcCurdy as a guest star.
33* HollywoodPudgy:
34** Jack regularly calls Will fat, but is the only one to do so.
35** There were a few rare barbs thrown at Grace by Karen (who usually called her boyish and flat-chested instead.) However, this showed clearly that this was deliberate. A few critics mentioned that the fat jokes thrown at Grace weren't as funny when Debra Messing was pregnant, showing that this was supposed to play off the ValuesDissonance of making fat jokes toward the slender [=McCormick=] and Messing, similar to the fat jokes made toward Vivian Vance during ''Series/ILoveLucy.''
36* HoYay:
37** Karen and Grace got to kiss far more than Will or Jack ever did.
38** Karen with Lorraine. Best summed up when Lorraine was trying to steal some of Karen's jewels. After the takes off the visible jewels, and the ones hiding in her cleavage, Karen merely responds, "And...?" Lorraine then spreads her legs further apart and ''more jewels fall to the floor.'' Karen's response? "Impressive. Had we met under different circumstances, this might be 'hello' instead of 'goodbye'".
39** The show repeatedly implies that Karen and her maid Rosario are more of a couple than Karen and her husband, possibly up to and including sleeping together.
40* MemeticMutation:
41** A marinara fuck. [[labelnote: Explanation]]Uttered by Debra Messing in the bloopers for the first episode of the revived series.[[/labelnote]]
42** "It's the Gay Pumpkin, Charlie Brown" brought the term "pocket gay" into the vocabulary.
43* RetroactiveRecognition:
44** In "Fagmalion" part four, Karen dated a handsome, intense maintenance man named Anton. About seven years later, his actor is providing the voice of a [[WesternAnimation/ThePrincessAndTheFrog handsome, less-than-intense prince-turned-frog.]]
45** She once had a Thanksgiving hookup with a plumber, at Stan's behest--played by Mullally's real-life husband Creator/NickOfferman, now well-known as [[Series/ParksAndRecreation Ron Swanson.]]
46** In the Season 8 episode "A Little Christmas Queer", Reed Alexander played Will's nephew, and the very next episode "Von Trapped" featured a young [[Creator/JennetteMcCurdy Jennette McCurdy]]. They both went on to star in ''Series/ICarly''.
47** Julian [=McMahon=] plays "[[NoNameGiven Guy]]", who chats with Grace in an elevator in Season 1.
48* MisaimedFandom: Megan Mullally has said that women constantly come up to her and say “I’m just like Karen. People at work tell me that all the time”. Mullally’s response? “You know what? The people at your office may not be giving you a compliment. You may be getting fired soon”.
49* SugarWiki/SheCanReallyAct: Music/BritneySpears is surprisingly convincing in her guest role as Amber Louise.
50* TearJerker: Grace revealing to her father Martin that [[spoiler: his best friend Harry sexually assaulted her as a teenager]].
51* ValuesDissonance: While the show was groundbreaking in its treatment of homosexual characters and plots, it leaned ''heavily'' into the NoBisexuals trope and treated people as either straight or gay with no in between. One Season One episode has Will and Grace separately befriending a handsome new man in their apartment building, and when he invites both of them over to dinner on the same night, they spend the whole evening trying to determine which one of them he's into, never even considering that he might be bi. A later episode featured Karen's cook hooking up with both Karen and Will, then explaining that he's pansexual; Will outright declares that pansexuality doesn't really exist and is simply something gay men claim to be when they're in denial about their "real" orientation.

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