Wow. This one was possibly more bizarre than last week's, but I think it was easily the best of the season so far. Creative pitches a Samsonite commercial to Don, but he's unimpressed even with Joey's Joe Namath impression, and after he chews Peggy out in a manner that's become de rigeur, she calls Duck, who just so happened to send her flowers for her birthday along with an invitation to come work as Creative Director at a women's-product-focused agency he's starting. She's flattered at first, but when she pieces together the fact that Duck got canned from Grey (the incident at the Clios may have been the last straw), her enthusiasm wanes, and he confesses that he's been a mess since whatever it was they had going on ended.
Meanwhile, the SCDP boys are going to see Muhammad Ali via the magic of closed-circuit TV, but Don decides to beg off to work on Samsonite, part of the reason being that he missed a call from California he knows is about Anna but is broodily postponing returning. Seemingly unaware that it's Peggy's birthday, he keeps her late to go over Samsonite, causing her to miss her own surprise birthday dinner, which in turn prompts her fetal boyfriend Marc to dump her right then and there. She then yells at Don about Glo-Coat only to get it back twice as good from him, and when she breaks down in tears in the restroom, it's the lowest she's seemed in quite some time.
Later, Don's recording ideas for Samsonite when his tape runs out, and when he looks for a new one, he comes across Roger's drunken memoirs. Don calls Peggy back in and jovially plays them for her, and Roger reveals that Miss Blankenship was, I think, a dominatrix or some such, while Bertram unnecessarily had his testicles removed, and all I can say is these are quite the revelations to air when everyone in the world but me is away for Labor Day. The ice broken, Don takes Peggy out to dinner, and she confesses that despite the constant pressure to get married, nothing does it for her like working. They also trade morbid family histories and discuss secrets they share before heading back to the office, ostensibly to finish up the work but really so Don can vomit rather profusely. Peggy then finds Duck literally trying to take a dump in Don's (well, Roger's, but he thinks it's Don's) office, which leads to Duck and Don throwing some hands before Peggy can get Duck out of there.
Later, Peggy comes back to check on Don, who is trying to get up the nerve to return that call but instead falls asleep with his head in Peggy's lap. Later, Don has a vision of a spectral but smiling Anna seemingly crossing over, and in the morning, he finally makes the call and learns that Anna has passed, and despite the fact that he surely knew that was happening, he breaks down, but Peggy is there not only to comfort him but also, in a way, to take Anna's place. Later, when she returns to see him, he seems at first like it never happened, but when he takes her hand, it's clear that their relationship has gone to a new level. Doesn't mean he's not going to chew her out next week, though. Just saying.
Talk then turns to the fight, and as we'll learn Stan is going to represent some bets to his barber, who's a bookie on the side. Danny puts twenty-five on Ali (or "Clay," as he was still commonly called) by knockout. After Ken gets some lines about how Liston's going to win and Pete tells us his heart often beats rather speedily thanks to a congenital issue, Don arrives, and after Harry gives him his ticket, Joey tells him about Stan's barber, and Stan opines that Ali would make a hell of an ad man. Don agrees and then amusingly follows by putting a hundred on Liston, and Ken hilariously makes an "Our god has spoken" gesture in the others' direction before Harry asks Don if he's going to join them at the Palm for a pre-fight shindig. Don tells him "Absolutely" in a tone only slightly more enthusiastic than he would use to announce his intention to attend an upcoming root canal party before calling the Samsonite team into his office, and after Creative leaves, Harry tells Pete and Ken that if it comes up with Jennifer, he did pay for the seats. Even though she's not my, or I suspect anyone's, cup of tea, I wish Jennifer were around more often so she could keep Harry from swinging whatever passes for his dick around.