1. In “The Doorway,” Don Draper is reading The Inferno.
The Inferno follows Dante’s descent into Hell, as he travels down through the incrementally horrible circles. It’s not quite that literal with Don, but Season 6 of Mad Men does show his journey to a very dark place — and it gets progressively worse with each episode.
2. Later in the episode, he gets too drunk and throws up at Roger’s mother’s funeral.
It’s really embarrassing. But it’s also one of the first cracks in the veneer. The audience is used to seeing Don as someone who’s suave, charming, and, above all, able to hold his alcohol. This Don — sweaty and sick — will recur throughout the season as he loses grip on his life.
3. In “Collaborators,” Don flashes back to an early moment of trauma while in bed with Sylvia.
He remembers seeing his mother having sex in the whorehouse where he grew up. His face when he returns to the present with Sylvia is contorted and, again, sweaty.
4. He then gives Sylvia money, as though she’s a prostitute.
He’s not really paying her for sex — the money is for her son Mitchell — but it reads that way. And it’s a low point for Don, at least suggesting that he’s now paying for something he used to get for free.
5. At the end of the episode, Don can’t even enter his own apartment.
He stands in front of the door for a moment before slumping against the wall.
6. Don starts to look visibly sadder: in “To Have and to Hold,” he stays in bed while Megan goes off to work.
Her role on “To Have and to Hold” has become more prominent. And yes, that title feels especially appropriate given that her increasing independence means that Don is losing his hold over her.
7. Later in the episode, he jealously watches Megan do a love scene, then seeks solace with Sylvia.
This is not the face of a casanova: It’s someone who’s looking for comfort because he’s barely holding it together.
8. In “The Flood,” Don drinks heavily after the assassination of Martin Luther King Jr.
He drinks more in Season 6 than in any past seasons. Behold, the less-than-flattering morning after.
10. Don is visibly scared when Ted flies them both in “Man with a Plan.”
And who could blame him! But it’s a significant image, as the audience sees Don looking flushed and queasy. And, perhaps more to the point, vulnerable. As a passenger on the plane, Don has relinquished all control to Ted; note how he uselessly grabs on to the strap.
11. His need for control plays out in his kinky sex games with Sylvia, but she gains the upper hand.
After an episode in which he degrades and manipulates her, Sylvia proves she’s still the stronger one when she’s able to walk away. That she does this after Don has been playing a hypermasculine, aggressive role makes him look all the more pathetic.
12. At the end of the episode, he’s still in shock, mourning his relationship as Megan mourns Robert F. Kennedy.
The space between them is key: As Season 6 progresses, Don also becomes increasingly isolated from everyone around him.
13. Don cannot handle his breakup with Sylvia, and he lurks outside her apartment in “The Crash.”
14. And the discarded cigarettes suggest he’s been lurking for a while.
They’re also a message to Sylvia, who will soon reiterate that she’s not interested.
15. Don begs Sylvia to come back, and when she refuses, he throws the phone against the wall.
He’s completely losing his cool. What’s ironic is that even though he’s clearly experiencing emotion, his telling Sylvia “I’m feeling a lot of emotions too” reads false.
17. Along with everyone else in the office, Don gets a shot of amphetamines in the ass.
But instead of giving him a much needed burst of creative energy, it sends him completely over the edge. He’s unfocused, confused, and — you guessed it — sweaty.
18. The longer his trip goes on, the worse he looks.
He hasn’t been sleeping well throughout Season 6, but now he’s literally unable to rest. And he’s losing time.
19. In desperation, he returns to Sylvia’s apartment.
Once again, the audience sees Don standing at a door without entering. Here he just puts his head against the door: It almost looks like he’s sleeping, but he’s standing up.
20. Meanwhile, he continues to flash back to his traumatic childhood.
The audience learns that the first time Don was with a woman, it was an act of rape by a prostitute. He’s sick and he doesn’t seem all that aware of what’s happening — all the control is taken away from him. This is Don before he was able to use sex to his advantage, when it was something done to him without his consent.
21. Back in the present, Don is more frantic than ever at work.
He appears desperate, which is not a typical Don Draper trait. And he looks like shit.
22. Once Don finally makes it to his apartment, he’s stunned to find he’s been the victim of a home invasion.
He wasn’t around to protect his wife, his kids, his home.
23. And now, at his lowest, he collapses, landing on his face.
For the first time in the episode, he’s able to get some rest, but it doesn’t exactly look comfortable. Also note how similar this shot looks to when he had his head pressed up against Sylvia’s door.
24. Eventually, he makes it to bed, looking worse than ever.
That empty stare. Those hollow eyes. This is the new Don Draper, and it isn’t pretty.
25. In “The Better Half,” Don has sex with Betty.
Perhaps he’s trying to relive his past glory. Either way, he wakes up alone.
26. Eating alone, he sees Betty and Henry together.
The look on his face underscores the futility of the previous night’s encounter: It wasn’t a successful conquest so much as a shadow of the way things used to be. And it leaves Don once again isolated, forced to watch his family — with a new husband and father — from a distance.
27. Don’s separation from Megan continues in “A Tale of Two Cities,” when he goes to L.A.
Megan calls Don because she doesn’t feel safe, but there’s nothing he can do from across the country.
28. He ends up collapsing on his hotel bed.
Alone again, naturally.
29. Later in the episode, Don attends a Hollywood party where he gets high and hallucinates.
Check out the vacant stare and the bags under his eyes — it’s like an amphetamine shot to the ass all over again.
31. Turns out he’s really drowning, and Roger has to revive him.
As party fouls go, nearly dying in the host’s pool might top the list. So much for Don making a good impression.
32. In “Favors,” Don manages to sleep with Sylvia again, but Sally catches them in the act.
Don with his pants around his ankles is one of the lowest points imaginable. The whole thing is shameful and embarrassing.
33. Don tries to catch up with Sally to no avail.
He’s panicked, which is something the audience hasn’t really seen from Don Draper before. Compare this Don with the one who stood up to Pete after Pete discovered the truth of Don’s identity. And for a man who’s always well dressed, there’s something especially unnerving about seeing him frantically tucking in his shirt.
34. In the lobby, Don can barely speak to the doorman.
He asks Don if he’s OK, because sweaty, vacant Don is clearly anything but.
35. Later Don returns home hammered.
Again, Don has been drinking too much all season, but it’s never been a more obvious escape. He looks toward Sally for forgiveness, but she avoids his stare. Don is a mess, as evidenced by Sally’s friend offering to cut his meat for him, because he appears incapable of doing it himself.
36. Things only get worse when Arnold Rosen shows up at the door.
There is fear in Don’s eyes: Does Sylvia’s husband know about the affair? Did Sally tell him? Actually Arnold is there to thank Don for helping Mitchell avoid the draft, but the terror is real. Don doesn’t have a handle on things, and he realizes the jig could be up at any moment.
37. Outside Sally’s door, Don pleads with his daughter to listen.
She tells him that he can’t talk to her anymore. Don has effectively lost any authority as a parent. Sally has seen him with his pants around his ankles, literally. And he continues to lie to her, insulting her intelligence as a young woman and destroying any trust she had in him.
38. He ends up returning to his room, resigned.
He ultimately can’t get Sally to listen, so he gives up. The shot of the hallway at the end of the episode underlines the new distance between father and daughter — as well as Don’s ever-growing isolation.
39. By “The Quality of Mercy,” Don is a shell of his former self, reduced to sleeping in the fetal position in a child’s bed.
Now that he’s lost control over his life and everyone in it, Don is infantilized.
40. Megan urges Don to slow down and take better care of himself.
For a while, he was at least able to put up a front of having it together. This Don isn’t even trying.
41. She goes on to tell him that he looks terrible, because he does.
Seriously, has Don Draper ever been less appealing? One could argue that he’s truly sick (or at least really hungover), but this new look is really just the culmination of a season-long downward spiral. To put it in extreme terms, his soul has been rotting from within, and now it’s finally starting to show on the outside.
42. When Betty calls Don to talk about Sally, he can’t even put up a fight.
Betty tells Don that Sally is no longer interested in staying with him. He’s mostly too drunk (or sad) to care, which Betty picks up on. Remember the volatility of their conversations in the past?
43. And when Megan comes home, Don continues his self-imposed isolation.
She reminds him that he can watch TV in the bedroom — with his wife at his side. But Don either doesn’t hear or doesn’t care. He’s a zombie.
44. At the end of the episode, Peggy confronts Don for his detestable behavior.
Again, he’s incapable of responding. She calls him a “monster” to his face, and he sits there in silence. He has no friends or allies, and no real desire to fight back.
45. Instead, he returns to the fetal position he began the episode in.
This is the last shot of the episode. At this point, it’s hard to imagine Don sinking any lower. He’s reached his nadir. But if that’s the case, what’s next?
46. In the season finale, “In Care Of,” Don continues to drink heavily.
He gets so drunk, in fact, that he punches a minister. Which is frowned upon in most circles.
47. And he winds up spending the night in jail.
“I shouldn’t be in here,” he says. The sense that Don is trapped has never been more apparent than it is now, with him literally behind bars.
48. The next day he tells Megan what happened, which means finally acknowledging that he has a problem.
So what’s the next step? Rehab? AA? No, Don wants to move to Los Angeles and start fresh.
49. He’s fully defeated.
This is the worst he has ever looked.
50. At the office, Ted actually makes Don drink to stave off the symptoms of withdrawal.
If the audience had any doubts about how serious his alcoholism has become, this scene drives it home. Don is visibly suffering from an addiction, to the extent that his colleagues have noticed.
51. His hands are shaking.
Delirium tremens is a classic symptom of alcohol withdrawal.
52. And finally, as he hits rock bottom, Don breaks down and starts to tell the truth.
He’s not purposely sabotaging the meeting with Hershey’s, but that’s essentially what happens. On the one hand, this is likely the beginning of Don Draper’s redemptive arc: He’s reinventing himself, perhaps as Dick Whitman. On the other hand, Don has never been worse at his job.
53. Don tells Megan that they can’t move to L.A., and she leaves, maybe for good.
His feeble “I love you” feels like too little too late.
54. At the end of the episode, Don’s partners force him to take an indefinite leave of absence.
This is what they did to Freddy Rumsen way back when — it’s the closest they can really come to firing Don. And given his behavior all season, can you really blame them?
55. Don has now lost everything.
“Going down?” Lou Avery asks. But Don is already at the bottom. His marriage is over, his kids are gone (Sally even uses the alias “Beth Francis”), and he’s out of a job. The only place he can go from here is up — but it’s going to be a daunting climb.