Great Moments in Mad Men: Season 5

Great Moments in Mad Men: Season 5


Season 6 of Mad Men is fast approaching and over the course of the season I’ll be documenting all the great moments in each episode. I’m sure they’ll be plenty to choose from.

Before that I’ve compiled a list from each season because let’s face it, there are some doozies. Take a peek and refresh your memory on what were in for come Sunday April 7th.

Disclaimer: If you haven’t caught up through season 5 I wouldn’t recommend reading the lists.



Nobody could ever make a list of Mad Men moments and not include the wondrous performance of “Zou Bisou Bisou”  by Megan Draper. You either love it or hate it there really is no in between, and believe me I’ve asked around. It was amazing the shit storm this one scene caused on the internet the day after.

I happen to fall on the love it side and not for the reasons you may think. I like to look at in terms of the bigger picture. This one performance sets the stage for multiple storylines and interactions throughout the course of the season. Not to mention it’s a killer way for Megan to break herself into the group.

The comments and looks that come from the musical number are priceless. But none are as great as Don and his utter confusion and dismay. He tries to hold it together but throughout he looks puzzled and like he might explode. Everybody leaves the party either horny or upset that their life isn’t as sexy as Megan in a short black dress. Plus leave it to Bert Cooper and his strange sense of humor and timing questioning right before she starts, “Did you buy him a pony?”



Harry and Roger don’t have many scenes together if at all but when Harry is asked to change offices a one-on-one discussion is necessary.  Throughout the series Harry has consistently acted foolish. Whether it be saying the wrong thing at the wrong time or being generally confused he’s quite the dope. He sticks to that behavior when he is called into Roger’s office immediately apologizing for something that wasn’t even the topic of the meeting.

Roger requests that Harry switch offices with Pete but in reality it’s not really a request. He agrees but only after Roger butters him up with cash, or more specifically $1100. Being the fool that he is Harry mentions that Roger will “owe him” and questions if this sort of transaction will be every month. All you can do is sigh, well and laugh of course.



I’m still not exactly sure if the whole “fat Betty” aspect of season 5 did anything positive for the show or if it was just too jarring. We all know January Jones is a stick so when we saw her in a fat suit all season long it was hard to focus on the actual story. It did make for some fantastic YouTube videos as you’ll see below.

She and Sally share some ice cream together and when Sally doesn’t finish hers Betty dives right in without skipping a beat. Her weight gain isn’t far off from what happens to many people after going through divorce or other big life event. It’s clear through her struggles and behavior throughout season 5 she isn’t dealing with things quite as well as Don.



Since Peggy is no longer a newbie at the agency she feels it’s okay to prop up her feet and have a drink with the rest of the boys. Roger finds this behavior ridiculous when he walks into her office asking for a favor. She even attempts to do some flirty maneuver asking what he had in mind when he asks, “What are you doing tonight?” Roger gets right down to business requesting/demanding that she work up something for Mohawk, an account he made clear was only for another copywriter Ginsberg.

Knowing that Roger is desperate she milks him for all he’s worth. Their back and forth is really due to the great acting of Elizabeth Moss and John Slattery. These two have really come a long way since Peggy was cautiously asking him for an office back in season 2.  Watch as she wraps him around her finger.



Every great show needs a dinner party episode and more often than not they are some of the best episodes in the series. Such is the case when Don and Megan attend a dinner party at Pete’s house with Ken and his wife. Really the entire dinner is one great moment as Megan can’t remember Cynthia’s name and Don ends up saving the day when the sink falls apart.

Don’t forget that’s the sink Pete supposedly fixed. As Pete struggles to find whatever tool he thinks will fix the sink again Don disrobes and solves it in a jiffy. Or as Cynthia puts it “Superman” comes to the rescue. I bet Pete wishes he never tried so hard to get Don in his house as all the women stand in amazement at Mr. Fixit.



When a series does their drug episode most of the time you can see it coming from a mile away who will be most likely candidate to participate in illegal activity. However, Roger is not somebody I would have elected as a candidate for a Mad Men drug episode. But this was the 60s and LSD was quite popular. That’s right, Roger does LSD and provides one of the most interesting episodes in the series.

There is some fantastic imagery as he stares at himself in a mirror with half white half black hair. Or when he opens a bottle of vodka only to hear a symphony come out of it. In rewatching the LSD scenes I saw something I didn’t see before and that’s when Roger sees Bert Cooper on a five-dollar bill. Trippy.  The best thing Roger experiences is when he sees right before his very eyes the world series from 1919 and laughs like a small child.



It’s become pretty clear that Roger will never stop misbehaving. When Megan’s parents come into town they along with Don, Roger and Sally attend an award ceremony. Megan’s mother Marie seems to be having some marital troubles with Emile and as a result becomes flirtatious with Don and Roger.

Roger and Marie escape into another room while she goes down on Mr. Sterling. In a very innocent move Sally walks into the room and see’s the naughty behavior. She stands and watches for a minute confused as any child would be but also seems very curious. Here we have Sally being corrupted, to be honest with parents like hers I don’t know where this girl will end up.



It’s uncomfortable to watch Peggy and Don fight since we know they have such an important past. Peggy was the most taken aback by Don’s new marriage and even though she tries to play it off I think even Don could feel some animosity. I’m not sure this comes from a place of jealousy but more from the perspective of questioning whether he really wants what Megan has to offer.

Eventually this tension leads to a blow up at the Cool Whip test kitchen after Megan has announced she’s leaving the agency. When Peggy keeps messing up on the tagline for Cool Whip she and Don argue about Megan and her place at the agency until she declares, “You’re not mad at me. So shut up.”  Then he does something magical, he shuts up. Who else can get Don to do that?



Everybody wonders from time to time what it would be like to be in a relationship with a certain someone. Whether it be what you think they’re like sexually or how they’d be as a roommate we all get curious. I always wonder what would it be like to be with Don Draper, especially if I were Megan and he’s just moved into a new phase of his life where he doesn’t cheat on women. I got a very small part of this answer during episode 9 in season 3.

When the kids return home from Don’s, Bobby drags home a piece of paper he drew on that was once a note for Megan. It reads, “Lovely Megan, I went to buy a light bulb. When I get back, I’ll see you better. Love, Don” I know I know, it’s cheesy as hell and for shits sake he’s an ad man…but still! I’m a sucker and for a moment I thought, “Well crap, that would be nice.” Even with all his bad qualities he does seem like the type to do sweet things like that note once and a while. In the end this note pisses Betty off and she in turn tells Sally about “Daddy’s first wife.” Such a dick move.



Don and Joan made it 4 seasons without even hinting at having sex with one another, although does anybody else remember that little kiss he gave her when it was announced he won the Clio? It was weirdly skipped over as she threw her hands back like “Oh my.” Moving on, Don goes out during the day to buy a car and takes Joan with him after she freaks out on the new secretary. She had let in a man that said he needed to talk to Joan about a surprise and that would be serving her with divorce papers.

After they pretend to be a happily married couple Don signs away a check  as collateral to take the car out for a a bar of course! He and Joan talk about her early days of getting flowers non-stop and terrifying all the men in the office. We’ve seen these two have moments of understanding before but never this in-depth. It’s little things like the sweet way he gives her his coat on their way out that makes it all so endearing.

Sure, they are flirting up a storm but Joan reels him in making him behave for once. They discuss a man in the bar that has been staring at Joan and what his wife might be like at home which produces one of the best lines from her (and here I pull the female card), “I bet she’s not ugly. The only sin she’s committed is being familiar.” She is probably right.



One of the biggest moments, but also the most necessary was when Peggy decided to leave the agency. While Don may come off as arrogant and upset initially it’s really that he is incredibly sad to see her go. He starts off with saying things like, “Let’s pretend I’m not responsible for every single good thing that’s ever happened to you.” Jesus Don, you gonna talk about Jesus again?

Then Peggy drops a line that shifts his mood, “You know this is what you would do.” She’s absolutely right, think about the guy that wouldn’t even sign his contract to stay at the agency. It is what he would do and he probably would have done it sooner. It’s so hard to watch as he kisses her hand and reminds us of an episode in season 4 “The Suitcase” where he grabs her hand and they just share a moment looking at each other. Here we have the connection that runs so deep with them being tested. Ultimately she does have to try something else, it’s almost what he set her up for.



Things have never gone right for Lane whether it be failed relationships in the states or uprooting his marriage from London. Although he has a comfy position at the agency things never really settled. Things only got worse as he faced financial troubles and let his behavior spiral out of control forging a fake bonus check with Don’s signature. This is particularly bad given the agency made a very clear announcement about no bonus checks for Christmas.

This isn’t kept secret for very long and with his trust now compromised Don asks that he resign. He then has a very bad last moment with Joan making a sexual comment she immediately dismisses and then shows up drunk at home to find his wife has bought him car. After failing to commit suicide in the car he travels to the office to write his resignation letter and hangs himself. While Lane wasn’t there since the beginning he held a special place in the show. His death wasn’t a complete shock given all that happened and the strange allusions to death all season but it makes a big impact on the show. I always thought Pete would kill himself first.



As Don and Peggy take a break from their office jobs they find themselves in a movie theater together. Like a true friend he tells her she looks good and asks how the new job is going. She tells him things are going well while he assures Peggy he’s proud of her and knows people move on when you help them he just didn’t know she would move on without him. It feels like something he should have said when she gave notice but was too distraught to admit.

As the movie starts she asks that he give her love to Megan and suggests they all get together sometime. When we first learned Peggy was leaving I don’t think anybody expected she’s be running into Don at movie theaters. As they talk about competing with one another for a ladies cigarette it’s easy to see her departure was a great move. She and Don still seem to share what they once had as the movie starts and they sit back.