On the Menu: Tallboy Oakland

Welcome to On the Menu, where we explore what makes a bar’s menu unique, intriguing, and all-around delicious.

Opened in May, Tallboy is the new project from bar industry vet Den Stephens (North Light) in collaboration with beverage director Zach Edwards. Aiming for both irreverence and accessibility, the Oakland bar serves a playful lineup of thoughtfully honed Martinis and cocktails, Jell-O shots, slushies, and a freezer stocked with premixed cocktail shots, dubbed “Cheekies.” We sat down with Stephens to find out how the menu came together, how to revamp a drink with a bad reputation, and what cocktail nearly ended his partnership with Edwards.

Imbibe: You call Tallboy a “cocktail dive bar”— what does that mean to you?

Den Stephens: Dive bars have always been the most democratic spaces in food and beverage. The hope was to say, “Why can’t we create a space for a lot of people to congregate that’s warm, unpretentious, inviting and has a lot of regularity?” Whether that’s price point, the service, a sense of familiarity both in what’s being offered and how you’re being treated. Why can’t we celebrate all these things that we love about dive bars but also make you a Martini that is going to change your life? Or a Daiquiri that’ll help you see god? That was the entire goal of this project … I wanted a sense of casual informality that belies the fact that we’re making really ambitious, well-crafted drinks.

What was your aim when building the menu?

We wanted it to be irreverent, cheeky, fun, and accessible. Any of the sort of “cocktail works” that we do, we wanted to keep that behind the scenes and present the drinks in a way that feels super accessible. From the beginning, it was essentially “‘tinis and weenies”—Martinis and hot dogs. I love Martinis—they’re one of my favorite cocktails, and I think there is a lot of room for interpretation in that genre. And I think the irreverence that we’re approaching these drinks with allows people to say, “Hey, I don’t know exactly what that means, but I’m willing to try it.”

How did you land on your lineup of Martinis?

We took a lot of inspiration from the late ’90s and early 2000s, going beyond just a sense of ironic detachment and saying, “We really respect these drinks.” The DNA of these drinks is really good, often something just needs to be tweaked to make it fit within a modern palate. Take the Lychee Martini. A lot of people have baggage with a Lychee Martini because they had a two-ingredient version that was too sweet and they paid $20 for it 10 years ago. So how do we make our version of that? We added fino sherry and a lychee liqueur but also lychee puree, with mezcal as the base. It’s floral, delicate, slightly smoky, and it finishes super long and dry. It’s eminently crushable.

And then we probably made 30 or 40 Appletinis before we landed on the one we have. I thought our beverage director and I were going to have the fight that finally broke us up after five years over this drink… But it was just about figuring out what made each drink sing, all while staying true to the essence of the drink. So the Appletini is crunchy, tart, kind of funky, and really fresh. We knew that we wanted to work with Sour Apple Pucker, because it’s a hallmark of that drink, and we knew we wanted it to be vodka based. But we’re also using fresh Granny Smith Apple juice, a 2:1 demerara syrup, lemon, and a tiny amount of overproof rum, which was the je ne sais quoi that kicked it over the edge. It’s my favorite, so of course, it’s our least-selling cocktail.

You have some playful categories on the menu, like the Cheekies shot and the Jell-O shots; why were those elements you wanted to incorporate?

Mainly just for fun. It’s this little crushable moment that lets you dip your toe in the water of the cocktail experience without pulling the trigger on an entire drink. I like a Boulevardier, but I don’t actually want a whole Boulevardier, respectfully. But an ounce is great. The format allows us to present them at a really accessible price point, and allows people to try a lot of different options. Plus it makes a really fun boilermaker.

The Jell-O shots were a fun template to revisit some of the Martinis that we thought were best left in the early 2000s, like the Porn Star Martini. I always wanted to love it because I love passion fruit, but I never really got the whole passion fruit-vanilla combo. So we took the vanilla out, we made it a Jell-O shot, and we call it the Onlyfans Martini. It’s one of our top selling items—we literally can’t make them fast enough.

What’s been the most popular drink on the menu?

It’s a dead heat between our Tallboy Martini and the Dirty Martini. People took the concept really literally, which is fun. We shake our Dirty Martinis, and we don’t double strain them—we want there to be that little raft of ice over the top. Frankly, it’s delicious. It’s a house-made brine, and we don’t put any vermouth in there. The Tallboy Martini is stirred, and it’s a 50/50. But we use Manzanilla sherry instead of dry vermouth, so it’s really dry with the saline character. We use two gins, Gordon’s and Bombay Sapphire, and it’s very aromatic. We express a lemon disc over the top for a lot of nice oil, but it still gets an olive, and a couple sprays of Jacobsen sea salt saline just to double down on the sherry. It’s a session Martini for sure.