rogueattorney
Adventurer
This ad is targeting people who played D&D roughly from 1975-1985 and then entirely left the hobby of RPGs. That's also the era that is approximately when D&D peaked in terms of total number of players. I think those people will be reminded of a fond memory that they had forgotten about until now. And the trigger of that ad will be enough for some of them to want to buy it for themselves and their kids.
I think this is right. Speaking as someone who lapsed as a customer of D&D in about 1994, but continued to be a rpg'er who played old D&D products and other rpg's, I had a hard time leaving the new box set in the store. In the end, I did leave it in the store and bought the Dragon Age boxed set instead. I knew that I would be dissatisfied with the D&D box because I knew about 4e and knew that it's not the type of D&D game I'm looking for.
Guys less dialed into the rpg scene aren't going to know these differences. The ad, the box, they look like they came straight from 1983. It's the rpg equivalent of picking up Def Leppard's Pyromania to rock out to while taking your kids to school.
But, yet again, I wonder what the reaction of these hypothetical players will be to this old-school aesthetic/new-school design. WotC might get them to buy the box, but will they get them to sign on as long-term customers employing a rule set that, in my opinion, bears little resemblance to the rule system these lapsed players are familiar with and are presumably nostalgic for? WotC must be quite confident of the self-evident improvement of the rules. I am less so.