- Peggy and her minion's new Running Gag:
- They're doing the voices from comedian Stan Freberg's hit novelty song "John and Marsha" (the moaning sounds in the voices simulate orgasm even though the two names are the only words on the entire record - scandalous for its day); Freberg, by the way, was also a famous pioneer of comedic advertising, including bits that are still regarded as classics - as an interesting parallel to Don Draper, in real life Freberg won over 20 Clio awards and steadfastly refused to do tobacco commercials.
- This exchange between Roger and Don upon arriving at the office the morning after a Christmas party that Lee Garner Jr. had been invited to:
Don: (In German accent) Did you enjoy the führer's birthday?
Roger: (Also in German accent) May he live for a thousand years!
- Alone and wifeless over New Year's, Don and Lane take in a movie. "You know what's going on here? Hand jobs." "Really?"
- Drunk. And the movie they're seeing? Gamera!
- "I'VE GOT A BIG TEXAS BELT BUCKLE! YEE-HAW!"
- "WE'RE NOT HOMOSEXUALS, WE'RE DIVORCED!"
- After a commotion in Don's office, Peggy's head sloooooooooowly peeks over the office dividers while Don is fixing himself a drink - and then ducks back down just as Don turns towards her.
- The Honda executive's response after his first look at Joan.
Honda executive: [in Japanese] How does she not fall over?
Honda executives: [all laugh]
Joan: They're not very subtle, are they?
Translator: [in English] No. They are not.
- Made even better by the fact that it's not clear if he's referring to the Honda execs or Joan's breasts.
- Peggy riding around in circles in an empty studio on a Honda motorbike.
- Danny Siegel's hilariously uninspiring portfolio in "Waldorf Stories":
Don: "Greyhound. The Cure for the Common Bus."
Don: "La-Z-Boy. The Cure for the Common Chair."
Don: "Budweiser. The Cure for the Common Beer."
Don: "Manufacturers Hanover Bank, The Cure for the Common...Bank."
- Turns into a Brick Joke when Don, in a drunken haze, uses Danny's tagline idea in his Life Cereal pitch. And sells it.
- Peggy calling Stan Rizzo on his claims about being a nudist and Peggy's inability to be anything other than Don's lap dog by shedding all her clothing, asking him to do the same, and then promptly (and constantly) checking to see how that erection of his is doing.
- Peggy's reaction to the work Rizzo had done at the end where she said that she changed just "a little bit" while gesturing with her thumb and index finger.
- The flashback of how Don got started at Sterling Cooper: Roger got totally hammered during their meeting and hired him, despite being thoroughly unimpressed with his work. And in the same episode, Don's drinking forces him into a similar corner.
- Trudy Campbell in "The Suitcase." In the bathroom at SCDP, she tells Peggy she's followed boxing all her life. "My father loved blood sports," she explains, delicately putting on her white gloves. Then when they go out to where the menfolk are waiting, she asks if they're ready to go: "I want a rare steak and to watch those two men pound each other." Who knew?
- Don and Peggy listening to the memoirs that Roger was recording for his new book and their reactions. Such revelations include Bert's disdain for Roger, Ms. Blankenship's sexual prowess back in the day, and an unfortunate surgery for Bert conducted by a one Dr. Lyle Evans.
- "FOR A GOOD TIME, CALL CAROLINE"note
- Duck entering SCDP late at night while drunk and desperate for Peggy is heartbreaking in general, but one scene is made funny when Duck cooks up the idea of relieving himself in Don's office as an act of revenge. He ends up targeting Roger's posh office recliner in confusion.
Duck: Would you let me concentrate?
- Three guys try to shake a vending machine in the right way to make the change (and a watch) it ate fall out, while Peggy comments "I feel like Margaret Mead."
- Then Pete comes out into to the hallway because the commotion disturbed his phone call: "When did we get a vending machine?"
- Miss Blankenship, full stop.
- Even her death is funny, at least at first. It culminates in the removal of her body viewed in complete silence from inside the conference room, with the staff trying to remove her from the building without their clients noticing, with Harry finally adding dialogue about the afghan they've stolen from his office.
Harry: My mother made that!
- And later on, Don asks something of Faye.
Don: I'd ask my secretary to do it, but she's dead.
- Sally and Don's french toast recipe.
Don: What's on this?
Sally: Mrs. Butterworth's.
Don: Go get it. (looks at bottle) ...That's rum; read labels.
Sally: Is it bad?
Don: (takes another bite) Not really.
- Don and Betty talking on the phone after FBI agents check in with her to ask whether or not Don is a secret Communist, and asks questions that throw Betty off because they remind her of the fact that he is actually Dick Whitman. As the conversation progresses:
- Trudy Campbell's maternity nighttime wear.
- In one of the episode commentaries, Matt Weiner says that he put in the script that Trudy would still wear small nighties while pregnant, but even he was surprised by how funny it became.
- Peggy making a presentation for Playtex with lipstick on her teeth, with Harry casually informing her about it immediately afterward.
- "You there! Get my shoes."
- The scene where Joyce tries to kiss Peggy.
Peggy: I have a boyfriend.
Joyce: He doesn't own your vagina.
Peggy: No, but he's renting it.
- Joan to Peggy in the season finale: "Whatever could be on your mind?", when the shock of Don suddenly marrying is the only possible topic. Followed by Joan stating that she learned not to seek satisfaction from the job. They both laugh when Peggy calls it bullshit.
- Roger's first appearance in the season premiere is amid the aftermath of an apparent orgy.
- Don in an L.A. restaurant meeting Pete who's been out in California for a few months and he's gone native, with a deep tan, wearing a polo shirt, a sweater around his neck, plaid slacks and gives a surprised Don a hug instead of a handshake.
- Ken, who still has an eyepatch over his injured eye, tries to throw the earring Joan left in his office and misses completely because he has no depth perception.
- Peggy, Stan and Ginsberg in an elevator. Peggy asks if Stan can work that night. Stan says he can't because he's going to a party.
Maybe if you invite me you can have til Tuesday? Stan:
And now we know you don't have plans for Valentine's Day. Ginsberg:
She has plans, look at her calendar. February 14th: ‘masturbate gloomily'. Peggy: [Death Glare]
- Dawn and Shirley's greeting each other in the break room by their own names as an inside joke how they're often mistaken for each other because they're the only two female African-American employees in the office.
- When Shirley tells Dawn that Peggy thought the flowers Shirley's fiance sent her for Valentine's Day were for her and took them into her office:
Shirley: Who the hell is sending her flowers?
- And the look of embarrassment on Peggy's face when she finds out that they actually were for Shirley and not from Ted.
- The SC&P partners have a conference phone call with Pete and Ted in California. As Pete tells a meandering story of how he was able to get a new client, Bert Cooper deadpans:
"Is this a partners meeting or the most tedious wireless program I've ever heard?"
Roger: "Look when I brought in Chevy I got their very own Mikey O'Brient laid! (To secretary recording the meeting) Sorry, sweetheart. And it wasn't easy! (Again to secretary) Sorry again."
- Betty's crack about Bobby's teacher's open blouse, saying that "they might grab onto the wrong set of udders."
Bobby: She likes you!
Betty: That blouse says she likes everybody.
- SC&P have bought a new computer and installing it into the room that was used as the creative bullpen. They're moving everything out and Ginsberg wants to take the couch and put it into the office he uses with Rizzo even though he tells him it won't fit. Ginsberg loses it and yells, "Damn it Stan, the other couch is full of farts!"
- Roger's secretary Caroline reading the message from his ex-wife Mona about their son-in-law, whom Roger had sent to get their daughter Margaret from a hippie commune in upstate New York:
"Hey, genius, Brooks is in jail in Kingston."
- The visual of Roger in his suit and Mona wearing a fur coat and jewels at the farm commune surrounded by unshaven hippies and seeing their upper class daughter now in hippie clothes and calling herself "Marigold".
- Mona trying to get Margaret to leave the commune:
"Sugarplum, these people are lost and on drugs and have venereal diseases."
- Stan discover's Lou's cartoon, "Scout's Honor" on the Xerox machine and shows it to the rest of Creative, who have a field day making fun of it.
- An irate Lou goes off at a meeting after overhearing Stan and a co-worker making fun of his cartoons in the bathroom.
You know who had a ridiculous dream and they laughed at him? Stan: You? [Cut to Don cracking up]
- Ginsberg's ever growing paranoia over SC&P's new computer starts off as this
- Joan and Roger's befuddled reactions when Cutler proposes that Harry be made a partner. Roger goes so far as to abstain from the voting by walking out of the room.
- And when Cutler asks for objections to the proposal, Joan follows suit.
- When Pete's girlfriend walks into Don's office, Meredith - assuming Don wouldn't welcome the intrusion - asks her boss if he wants her to page him in 10 minutes as a way of getting rid of the visitor. It's the loopy nature of Meredith's delivery (as well as the wink she gives Don and Don's bemused reaction) that makes it all the better.
- While on the plane ride to NYC, Bonnie and Pete join the Mile-High Club. One can tell Pete is unable to believe his situation.
- In "Waterloo" the scene with Meredith and Don in his office. Her complete seriousness and starting by telling Don to sit by patting the couch makes the scene so funny.
Meredith: Look at you. You're so confused. You never even met with Commander cigarettes. I would have known.
Don: It doesn't matter.
Meredith: I want you to listen to me. (takes his chin and turns his face toward her) I know you're feeling vulnerable, but I am your strength. (kisses him) Tell me what I can do.
Don: You can get my attorney on the phone, and we can't do this.
Meredith: You're right. Not right now.
- The look on Don's face after she kisses him is hilarious. It's less shock and more "Um......no."
- Julio, the 10 year old boy who lives upstairs from Peggy and whom she formed a bond with sadly tells her he and his mother are moving out:
Julio: "I don't want to go to Newark."
Peggy: "No one does."
- When Roger informs the partners that, in his attempts to undermine Cutler's coup, he set up a deal to sell the agency to McCann, everyone aside from Cutler votes in approval. Eventually, even Jim agrees to it. When Roger shoots him a surprised look, the response he gets is:
- Pete's realization when Roger informs Joan that this sale means she will get a one million dollar windfall because she owns five percent of the company:
Pete: (ecstatically puts a hand to chest) "And I own ten percent!"
- Harry notices an impromptu meeting gathering to discuss Cutler trying to force Don out.
Harry: Is this a partners meeting?
Joan: You're not a partner yet.
- There's probably some sort of absurd humor in Cooper's sendoff song and dance number, just so we can put it on every moment page.
- Don's face during the whole thing basically boils down to "What the hell am I witnessing?"