These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Arc Fatigue: Season 6 received some criticism because the story doesn't advance as evenly as the previous seasons, with most of the exposition being in "For Immediate Release" and the last three episodes, and with a few retread episodes like "A Tale of Two Cities."
Award Snub: Season 5 received 17 Emmy nominations, among the most the show's received in a single year, and walked away with 0 wins.
As of Season 6, the show's received a total of 31 acting nominations and has never won.
"The Other Woman" provoked some extreme reactions in the fandom.
Megan and her relationship with Don are this. She's revealed herself to be far more than the cutesy secretary and trophy wife she initially seemed to be, but some fans are still mad that Don didn't end up with Faye. Or they just don't want Don to find romantic happiness. Also, Megan's ambition, and particularly her desire for an acting career, make her out to be a strong independent woman to some, a selfish talentless egomaniac to others.
Continuity Lock-Out: In addition to the character development, the gradual change of time from 1960 to 1968 really adds to the viewing experience.
Creator's Pet: Glen. Played by the producer's son, he increasingly moves into this role as it becomes harder and harder to tell if he's supposed to be a Creepy Child or the kid just can't act.
To some extent, Betty Draper in the early seasons. Both Weiner and her actress claim that she will get more understandable and pitiable, if not sympathetic later on. However, it soon becomes harder and harder to tell if she's actually meant to be pitiable in the first place as her abuse of Sally escalates, or due to January Jones's bad acting.
Megan Draper, particularly in Season 5. A sizable contingent was turned off at how hard Weiner and the show was trying to sell her as the perfect woman who was just "good at everything."
More or less everything about Don's sexual behavior after it is revealed in "The Crash" that his first sexual experience was to be raped by a prostitute when he was a teenager. And then he was beaten with a wooden spoon for it by his adoptive mother. It... explains a lot. There's also the fact that his mistress for most of season six, Sylvia Rosen, has a beauty mark in the same spot as the aforementioned prostitute.
Every scene with Pete's hilariously senile mother in Season Six becomes this after Manolo marries her and then murders her for her money.
Pete jokes in season 3 that "Moneypenny" (Lane) "hasn't self-destructed yet."
In an odd combination of this with Hilarious in Hindsight, the doctor Joan goes to for an abortion in Season 4 (before she changes her mind) is in Morristown, New Jersey. A mere five years later, in 1970, New York adopted abortion-on-demand up to the 24th week, while it remained completely banned in New Jersey until the decision in Roe v. Wade in 1973.
Roger complaining in "The Color Blue" about how he 'found' Don. We learn in "Waldorf Stories" that he didn't think a thing of Don when they met - and at the very least only hired him because he was black-out drunk, and may not have actually hired him so much as Don just convinced him that he did and forgot about it.
While discussing the film adaptation of 'The Best of Everything' with Betty, Don mentions how Sal couldn't stop talking about Joan Crawford, a famous gay icon of the 50's and 60's.
Sterling mentions getting drunk and trying on the suit of armor in Lane's office. Sounds like something his son in another franchise would do...
Megan reads an audition script for Dark Shadows and is soon ranting about how terrible it is. This episode, itself titled "Dark Shadows," happened to air on the very weekend that Tim Burton's film version of the classic soap opera was released.
Peggy's mother admonishes her for cohabitating with Abe, advising her to get a cat instead. In season 6, she breaks up with him and does just that.
Ho Yay: Don and Roger, the epic bromance of the Sixties. They drink and womanize their way through the show, and while they may fight, they always make up. In season three, Bert Cooper stages an intervention for them when their fighting (over Roger's second marriage and Don's lack of respect for Roger) causes problems at Sterling-Cooper, and their reunion assists in finalizing Sterling-Cooper-Draper-Pryce. Don's conversation with Roger in "The Suitcase", with Roger begging Don to accompany him to dinner (albeit one with Freddy Rumsen and Cal Rutledge, neither of whom Don or Roger like) is even more Ho Yay-ish than usual:
Roger: I've still got your ticket. Don: It's an attractive offer. Roger: Look out your window, see me waving? Don: (smiling) Goodnight, sweetheart.
Sal has a crush on Ken Cosgrove, which he attempts, all too subtly, to get across in "The Gold Violin." By remaining completely oblivious, Ken doesn't really do any more to dispel it than he does to encourage it, so at end of the episode it's still just hanging depressingly in the air.
What about Don and Lane Pryce in The Good News (season 4, episode 3.) Lane is in the doghouse with his wife so Don takes him out for a nice dinner, they all get very drunk, act rather Ho Yay-ish to each other..their behaviour is even lampshaded by a comedian who sees them in the crowd and makes jokes about how they are a cute couple.
Which makes "Commisions and Fees" (Season 5, episode 12), where Don demand's Lane's resignation for embezzling from the company, followed by Lane committing suicide, all the more depressing.
Joey receives some compliments from Harry Crane and immediately tells his buddies that he's being hit on by an old queen. This is more likely a manifestation of Joey's tremendous narcissism than a sign of any conscious attraction on Harry's part. (Subconscious could be another matter...)
Magnificent Bastard: Don Draper is the best of them. Duck and Pete both try and fail. Peggy is rapidly becoming one. Bert Cooper is one when the situation calls for it. Roger has his moments but his propensity for killer one-liners far outshines his actual cunning.
Mary Sue: There is some feeling among some of the fandom that there are a few too many "Peggy is awesome" moments without her having the counterbalancing failures and torments that afflict others, such as Joan, Don, and Sal. (Her pregnancy storyline being a notable exception.) This could partly be attributed to the fact that Peggy is simply not as morally corrupt as most of the cast, rather than being especially great on her own. It is really is that cynical of a show.
Just about every man on the show falls is enamored with Joan to a strange degree, though this is balanced by her obsolete office politics and marital turmoil.
Megan's initial entry in Season 4 and 5 had hints of this: She was perfect with Don's children, seemed to have 'cured' him of his serial adultery, comes up with the perfect idea for the difficult Heinz account, adeptly rescuing it at dinner when they are about to be fired. However, in "The Phantom", she is shown to be selfish and a tad naive, and later episodes show Don slowly slipping away as she gets more successful in her acting career.
It's getting to the point where he can't shut it off.
Misaimed Fandom/Do Not Do This Cool Thing: Some viewers seem to genuinely view the show as a depiction of "the good old days". They also tend to hate Betty Draper the most for being the character that rains on their parade for showing how "the good old days" could really wreck a person.
Any chance that the majority of the audience might have had to sympathize with Duck Phillips disappeared along with his dog, Chauncey.
Also, Greg, Joan's fiance, crosses this line when he rapes her.
Pete finally crosses it late in Season 5 when he tries to convince Joan to prostitute herself as a pure business decision. Bert, Roger and Lane's tacit acceptance seem to make it a Moral Event Horizon for SCDP itself since the agency's big account has a shadow, one that is pointed out by a few characters.
Real Women Have Curves: Peggy is contrasted with more thinner and/or buxom women like Megan, Joan, and Betty. Yet Peggy is a rounded petite woman with "Hellenic" features (despite being Norwegian and...something Catholic) and is the representative for the ordinary women and their advances of the 1960s.
Pete-fucking-Campbell, initially. He undergoes major Character Development, develops a conscience, is unexpectedly the guy at SC/SCDP who is most aware of the social change on the horizon, and eventually swallows his own pride. By the end of Season 3, he actually knows the meaning of love and of remorse. However, all of that character development doesn't make the moment in Season 5 when Lane Pryce kicks Pete's ass any less satisfying.
Though pimping out Joan to hook Jaguar certainly didn't help his development.
As of season four (and to some as early as Season 3), Betty had become this for a lot of viewers due to her treatment of Sally, along with possible backlash from January Jones' acting in X-Men: First Class along with the show itself, along with a degree of Values Dissonance. It's not unusual to look at message boards and blogs and see comments like "I liked this episode a lot. Probably because Betty wasn't in it." The Huffington Post has even considered her one of the worst characters on TV(through the media itself is a bit more mixed). Changed in later seasons when Betty would be featured in less than half the season's episodes and Megan was getting the big sell.
Bob Benson. Too much screentime indicates he's a Mauve Shirt but he's received almost no characterization. He's an undeveloped character on a show that goes into nuanced and detailed examinations of its characters and the payoff is nowhere in sight. YMMV on whether said payoff worked.
Except the payoff did occur in the last three episodes of Season 6 where he was revealed to had a crush oh Pete, and that all of his references were made up. His background is basically that he's a younger Don Draper
Seasonal Rot: Some fans have accused Season 6 of running into this, due to some strange episodes.
Don't forget Trudy Campbell, whether she knows it or not.
Strawman Has a Point: In Season 2, Don is visibly displeased when Duck tries to bring on American Airlines and forces Sterling Cooper to dump Mohawk Airlines. While Don attempts to argue against it using customer loyalty, it's fairly clear he's opposed because he's not the main attraction.
Greg Harris isn't the most sympathetic character, but his reaction when Joan arrogantly stars to dissect his job interviews is understandable, especially when she smashes a vase over his head.
The Woobie: It's a testimony to the writing of the show that basically anybody but the British overlords can be Woobies. Few of them are pure Woobies though; the vast majority of the characters have both Woobie and Jerk Ass moments.
Sally Draper, thanks to Character Development; Pointing out the various things the adult Sally will have to discuss with her therapist has become a running gag in the fandom.
Sal, especially in "Out of Town" and "Wee Small Hours," and his wife, Kitty.
Don's secretary Allison, after he pretends their sexual tryst at his apartment after the office Christmas party didn't happen and continues on for days like that. She finally has enough and throws a paperweight at his head and quits.
Anna Draper hits Woobie status in 4.03 when we find out she has terminal cancer.
Lane Pryce. His superiors at PPL frequently take advantage of his inability to stand up for himself, he has an unhappy marriage, his father is still abusive (physically and emotionally) toward him in his forties, he isn't respected by most of the other partners despite being one of two people holding SCDP together, he falls in love with Joan but she's not interested in him (his obnoxious means of hitting on her don't help), and after Don finds out about his embezzlement and forces him to resign, he commits suicide.
Michael Ginsberg, after we learn his backstory that he was born in a concentration camp and that the man viewers assumed was his father actually found him in a Swedish orphanage when he was five.
Beth. It turns out that her husband has had her subjected to electroshock therapy on many occasions. In "The Phantom" he brings her in for another session because she is depressed about him cheating on her. Worst of all, she actually thinks that this is for the best.
Megan, as her marriage to Don becomes increasingly unhappy.
Kenneth Cosgrove had his foot broken and was shot in the eye before he left the Chevy account and was chewed out for it, while he was still wearing the eyepatch.