Our beloved Mad Men kicked off its final seven episodes of its seventh season on Sunday (hello alliteration), and while I’m so glad it’s back, I’m equally sad that these will be the last seven stories we’ll get to see of Don and company as they head into the 1970s and into the abyss of New York City forever.
While Mad Men has obviously provided us with plenty of “mad men” over the years, there are definitely some better than others. And although #ManCrushMonday is technically purely about attraction, I’m bending the rules a bit today and ranking the Mad Men on their overall likability, because frankly, in a male-ruled world of advertising in the 1960s, there are a handful of egotistical, cheating, at times misogynistic douche-bags, so they can’t all be crush worthy in the traditional sense. So if there’s anything Mad Men has taught us, it’s that there’s more to people than it seems on the outside, and it’s that very complexity that makes us, as human beings, interesting and worth knowing. These are the men that have kept the world’s attention for the past eight years, and the ones we’ll miss the most.
12) Bobby Draper
The fact that four different kid actors have played Bobby is reason for him to make the list alone, and a running joke throughout the series (to the viewers, at least). It’s the current Bobby that has really taken the cake, as well as the title for longest-held position as Bobby Draper. He can actually act and not just spit out lines, and he’s sassy at that.
11) Harry Crane
So Harry Crane is kind of a dud. He may have started Sterling Cooper’s TV division but just makes poor life choices. He’s cheated on his wife (but I guess, who hasn’t), he’s a pushover – he asks Roger for a raise from $200 to $310, and Roger gets him to accept $225 and Harry is super stoked about it. He’s often ignorant and can be dumb, and Don doesn’t like him. I guess what I’m saying is, there’s a reason why he’s on this list… but I just can’t pinpoint why.
10) Pete Campbell
The things Pete Campbell says are usually arrogant and offensive, he is always seeking approval and resents his co-workers when they find their own successes. He’s a white child of privilege who gets away with sleeping around and being a double standard. He has a face that is extremely punch-worthy, so when you see scenes of him getting into fights or walking into walls or falling down stairs, it brings you pure joy. Pete may be the biggest douche on the show, but at least he’s interesting. He’s like a car crash on the side of the road that you can’t help but slow down and watch.
9) Freddy Rumsen
Freddy had a rough start. When we meet him, he’s already hammered, and he stays that way for most of the earlier seasons. It’s no surprise that Freddy is an alcoholic, seeing the environment he works in, but when it comes to a point when he unknowingly pees his pants right before a huge presentation, it’s a problem. Incidentally, that pee incident led to Peggy stepping up and pitching a campaign which ultimately helped her move forward within the company, and it was always Freddy who believed in her talent. He showed up sporadically throughout the rest of the series, and when he becomes sober, the tables are turned and he’s the one confronting a drunken Don. For a man whose life seemed to be in shambles at the beginning, he’s one of the only ones that seems to have it together in the end.
8) Ken Cosgrove (Accounts)
Ken Cosgrove is the Bob Vance of Vance Refrigeration of Mad Men. He’s one if not the only one who actually has good intentions and is constantly the guy you can count on. He always wants to be the best at his job and tries not to get caught up in the drama or politics at work. Instead of cheating and drinking excessively, he spends his time writing sci-fi stories that get published in magazines, and I’m pretty sure if Ken was alive and real today, he’d be one of those cult writers signing books at sci-fi conventions. And he’s unintentionally endearing, since he doesn’t exactly have the best of luck. He lit’rally got shot in the face by a client and has had to wear that eye patch for a couple seasons. Also he’s married to Alex Mack.
7) Michael Ginsberg
We meet Ginsberg (played by the delightfully handsome and charming Ben Feldman) in season five, when Peggy wants him on board as a copywriter. He seems a little off when they first hire him, which is obviously foreshadowing of his future at Sterling Cooper Draper Pryce. He’s got good ideas, but unfortunately for him, Don doesn’t care much for him. And poor Ginsberg, when a huge-ass computer takes over the office, he slowly starts to go crazy. His proclamation of being a martian is truly Xenu-worthy, and his paranoia that the computer somehow transmits signals to make men engage in gay sex takes over his brain. He eventually professes his love for Peggy and in the most shocking/disgusting scene since the lawnmower/foot incident of season 3, Ginsberg hands Peggy a box containing the severed nipple he just cut from his person. Honestly, I just feel really bad for the guy.
6) Stan Rizzo
Stan joined SCDP in season 4 as the art director and was this misogynistic type who flirted with every woman that passed by. The one woman who hasn’t reciprocated romantic feelings for (and never should) is Peggy. It’s their relationship that ranks him at number six. They literally bare their souls for each other by actually stripping down and for the last few seasons, we’ve seen Stan turn into seemingly the only stable mad in Peggy life since Don goes off the deep end as we approach the 70s. Stan and Peggy have both helped each other evolve into better people, and that’s really all you can ask for in world where it seems everyone’s going downhill.
5) Sal Romano
SAL! I miss Sal. A lot of fans miss Sal. Ever since he made his last appearance on the series in season three, people keep asking when he’s coming back. Unfortunately the answer to that is never. The closeted art director who was married to a woman and finally had a tryst with a bellhop but then when a big-time client tried to come on to him, Sal refused and in turn the client forced Don and the other bosses to fire Sal. It was a super warped sexual harassment case that was sad to see play out on TV, especially knowing how difficult it was to be gay back then, and comparing it to the world we live in now.
4) Don Draper
Even if you haven’t seen Mad Men, you know that Don Draper isn’t exactly the most moral protagonist. He’s no Walter White, but he’s no Phil Dunphy either. In the pilot, it’s not until the very end that we find out that the womanizer we meet in the beginning actually goes home to a wife and two kids in the suburbs every night. While Don may be the head honcho at work, his secrets, as we come to find out, are deeper and more complex than we ever could have imagined, and that’s why he’s such a flawed character. Even in the title sequence, we see a man in a suit free falling from the top of a building, and it seems as if Don has been living a parallel life to that image for the past seven seasons. We don’t know where and how he’s going to end up, but like the promo pic above – he may be in over his head soon enough.
3) Dick Whitman
Speaking of Don’s secret background, we find out that Don is actually Dick Whitman. After taking on the Don Draper persona from a fallen fellow soldier in the war, Dick Whitman “dies”. But in a turning point in the show, we get to see not only the real Dick Whitman’s origins, but his interactions with the late Don Draper’s wife, Anna. That guy who shows up to Anna’s door to tell her that her husband is dead is someone we’ve never seen before. He’s a compassionate, almost shy man who is the complete opposite of the often arrogant Don Draper. In any scene with Anna, we get to see the real Dick Whitman – the one that happily provides for a widow, spends every Christmas with her, and gushes about how much he loves Betty when he tells Anna they’re going to get married. Fast forward to years later, when most of the people close to Don not only know about his sordid past, but don’t hold it against him – a feat he’s had since the beginning. Now we just have to see if he can get over his past himself.
2) Bert Cooper
Bert provided the Cooper of Sterling Cooper, founding the company with Roger Sterling’s dad in 1923. He basically played the seniority card throughout the show, often walking around without shoes (because he didn’t have an office), staring at his Rothko paintings, and providing excellent advice to the young blood around the office. Bert was like the strong grandfather of the office who everyone trusted. He was smart and loyal and frank – and to that I say, Bravo.
1) Roger Sterling
Roger Sterling has so many faults. He, again, like many others in the show, is an adulterer, constantly drinks and smokes, gets naked, participates in orgies, has threesomes (and ends up having a heart attack), gets high on LSD, and says the most inappropriate politically incorrect things to clients and co-workers alike (and has a book to prove it). But like other memorable TV characters like Dwight Schrute and Ron Swanson, they all have their own quirks and oddities and beliefs that we may not agree with, but it sure is fun to watch it play out. And I’ll miss that.
(Dis)Honorable Mentions: Dr. Rapist Greg Harris, Henry Francis, Ted Chaough, Duck Phillips, Jim Cutler, Glen Bishop, Bob Benson
Cookies + Sangria 
