The Waldorf Astoria’s Art Deco lobby is seasonally attired in lighted wreaths, but the ballroom pumps disco and upbeat ’80s pop while a huge screen flashes ancient brand names. Shearson, Braniff, Handi-Wrap, and Meister Brau share the Jeopardy!-like grid with hardly-knowns like Lucky Whip, Kool Shake, and Nudit.

Groggy after a night of drinking with a couple of old lacrosse buddies from college, Tim Miller takes his place in the crowd of about 50, his friend Dickie Grieves beside him for moral support. It’s Dec. 8, 2010, and the Eastern Shore realtor—he’s never been to New York’s Waldorf before—is nervous. Read more.