To celebrate final ‘Mad Men’ season, let’s look back at Don Draper’s hottest messes

04/10/2014 6:17 PM

04/19/2014 7:21 PM

When we left him in the finale of last season’s Mad Men, ad man Don Draper had performed an incredibly self-destructive act, blurting out the truth about his hard-luck upbringing as the son of a prostitute at a pitch meeting with Hershey’s. Or was his breakdown actually a brilliant, subconscious, last-gasp attempt to save himself from the ocean of lies in which he has been drowning?

We won’t know the answer until this season plays out, starting at 10 p.m. Sunday on AMC. Season 7 is Mad Men’s last, although that description is something of a tease: There are 14 episodes left, and the network took a page out of its Breaking Bad handbook and plans to split the season in half, showing seven episodes now and the rest next year in what can only be described as a plot to drive fans insane.

So in honor of Matthew Weiner’s terrific series that is less about advertising than it is about a changing America, we remember Don not at his best but his worst. He is, in the words of actor Jon Hamm to Time magazine, “a miserable drunk” whose partners ordered him out on sabbatical at the end of last year. Then, in what may be only his second honest act in the series, he drove his three children to the slums to eyeball the decrepit wreck of a house he grew up in.

Will Don’s spiral continue, or will he be redeemed? Either way, here are the worst mistakes Don has made so far:

• Rejecting his brother Adam’s attempt to reconnect. Sure, he gave Adam some money, but his refusal to bond further led Adam to depression and eventual suicide.
• Almost every moment he spent with first wife Betty (January Jones). He changed his identity and lied about his past; he spied on her visits to a therapist; he slept with every attractive woman in Manhattan and beyond.
• The other women. So, so many other women, from Midge, his hip mistress in the Village in the show’s first season, to department store owner Rachel (who shockingly threw him over) to consultant Faye Miller, cruelly discarded for the younger Megan, who would become Don’s wife. Oh, and there was daughter Sally’s teacher and … well, we could go on, but you get the idea. Don’s romantic dance card was always full, and everything ended badly. Sometimes very badly. Such as the time he was …
• Being so careless while carrying on with his neighbor Sylvia (Linda Cardellini) that his teenage daughter walked in on them and got quite an eyeful. Also a bad idea: allowing the same teenage daughter anywhere near the equally badly behaving Roger Sterling (the epic and dapper John Slattery). With these two men in her life, Sally doesn’t need a sex education class, though a therapist might be in order.
• Abandoning Megan (Jessica Paré) at the Howard Johnson’s in Plattsburgh after a fight and driving away. Which brings us to …
• Telling Megan in last season’s finale that he won’t be opening the firm’s branch in California after she has quit her soap opera gig to follow him there. He’s apologetic. She’s furious. “I don’t even know why we’re fighting for this,” she tells him. We’ll see if they’re still fighting for it Sunday night.
• Not taking his protege Peggy Olson (Elisabeth Moss, who like Hamm could use an Emmy) seriously enough and losing her to a business rival. The show’s best moments have always been about Don and Peggy, one of them representing the past and the other a symbol of the future, and her gentle resignation crushed him. Of course, now she’s back under his thumb.
• Not throwing the vile Pete Campbell (played to oily perfection by Vincent Kartheiser) out a plate glass window at any point in the series. Pete Campbell is awful enough to make you long for an AMC crossover with The Walking Dead. Pete can’t even drive a stick; surely he’d have no chance against bloodthirsty zombies?
• Not sleeping with Joan (Christina Hendricks), ever, not even after that lovely moment in the bar at Christmastime. Don! Have you not LOOKED AT HER?
• Impregnating Betty with that third kid — what’s his name, Eugene? — when their marriage was clearly over. The Drapers already had Sally and Bobby, and they get a fair amount of airtime, especially Sally (Kiernan Shipka). But by creating Gene, the Drapers saddled the writers with a kid too small to merit a worthwhile storyline.

Now: How about a couple fingers of Canadian Club?

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