What You Get: A Gold Plaque
The cocktail menu at The Roosevelt Room is more like a billboard than a menu. It stretches across the wall behind the bar, encompassing seven different eras from the “Early Years” (the birth of the cocktail through 1880) to tiki (1930s-1950s) to the “Dark Ages” (1950s-1990s) and beyond. That means there’s everything from classic stalwarts like Sazeracs and Aviations to once maligned drinks like Long Island Iced Teas and White Russians. Drink your way through the entire menu and you’ll be rewarded with immortality—well, in a way. Once you drink your way through the 50-plus cocktails you’ll get your name engraved into a gold plaque mounted above the bar. You’re limited to six drinks per visit, so plan accordingly.
The Bar: The Riddler, San Francisco, CA
What You Get: Embroidered Bomber Jacket
Try 100 of the Champagnes on the menu (which is most of them) at this SF Champagne bar and you’ll earn yourself a place in the Riddler 100 Club, which comes with a gold-embroidered black bomber jacket. It’s like belonging to the girl gang from Grease—but much, much cooler. While 100 bottles might seem like a lot, you’ll have no problem finding a reason to return to the chic and airy wine bar over and over again. Between food like tater tot waffles, expertly curated wines and adorable little touches (reserved tables are marked as being reserved for female icons like Michelle Obama and Beyonce), it won’t be long before you fill your scorecard. Bonus: You can even drink out of a Chambong.
What You Get: A Fez, a Trip to a Distillery and More
The Rumbustion Society at this San Francisco tiki stalwart began the day the bar opened in 2009 and was an immediate success. Owner Martin Cate had hosted a similar club, the Kill Devil Club, at his first bar, Forbidden Island, and knew he wanted to continue the tradition at any future bars. And he followed through: As you’ll see, the Rumbustion Society is not Cate’s only club. In the Rumbustion Society, customers essentially go through a self-guided master class in rum. There are levels to climb and, as you go from one to the next, achievements to unlock. As Cate puts it, he added a “gamification element.” Guests drink their way through three different levels: Disciple of the Cove (20 different styles of rum sampled in one-ounce pours), Guardian of the Cove (80 more rums sampled in two-ounce pours) and Master of the Cove (another 200 rums). Once you pass a (very easy) quiz after completing the first level, you are awarded a Rumbustion Society card and merit badge. Complete the second level (and take the oath of allegiance to Smuggler’s Cove) and receive another merit badge, a brass plate on the wall and a red fez. You also get to attend private tasting events. Finally, once you complete the third level and become a Master of the Cove, you get a limited edition tiki mug and a trip to a rum distillery. If you dare to go above and beyond and sample 500 rums, you become part of the Black Tassel Brigade, which earns you a black tassel for your fez and other, secret benefits.