Cocktail Culture: Jessica O’brien

Jessica O’brien Makes Weekly Cocktail Masterpieces At Sister

Robin Babb
7 min read
Making Drinks with Mass Appeal
Jessica O'Brien mixes up a custom cocktail for her Monday night pop-up (Eric Williams Photography)
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If you follow Sister Bar on social media (or, you know, if you actually go to the bar), you’ve likely seen one of Jessica O’Brien’s cocktail creations. At the start of every week, O’Brien creates a new special cocktail for Sister and serves it at Jayo’s Cocktail Pop-Up every Monday night from 6pm to closing time (or until they run out). The drinks she makes are anything but ordinary: expertly balanced, flavor-forward drinks that look about as good as they taste. The Weekly Alibi met up with O’Brien recently to chat about her creative process and the critical recognition she’s gotten for her drinks.

Alibi: Did you go the bartending school route?

O’Brien: No, there was just one guy that I learned from in San Francisco. His name is Rich. Me and him just got along. I was bartending at this bar. And one day he was like, “Jessica, you have a palate. Get behind the bar with me. Let’s start learning some shit.” So he kind of took me under his wing and taught me everything I know. So it was like, the School of Rich.

Where did you bartend in San Francisco?

There’s this place called The Cavelier, it’s right on Fifth and Market. It’s attached to this hotel called Hotel Zetta. So I bartended in the hotel lobby bar. I miss the Bay sometimes. But I grew up here. I moved back so that I could travel, because I wasn’t able to save any money out there… [Before I moved back to New Mexico] I was emailing this place [Sister]. I emailed them like 10 times saying “I want to work at Sister. This is where I’m going to work.”

So you got the job before you even moved back out here?

Pretty much. I still had to have an interview and all that stuff. And then I worked at Artichoke Cafe for a minute when I first moved back. But then they asked me to do the cocktail program here, so it was clear this was gonna be my full time.

In the two years you’ve been back in New Mexico, you’ve gotten a lot of recognition here.

Yeah, it’s really cool. Trying to introduce people to cocktails is interesting … Not everybody’s gonna be able to just go jump into a Manhattan or Old Fashioned. That’s what I like to do … I wanted to go to culinary school first, before I even thought about being a bartender. But this is incorporating a lot of my cooking skills obviously. Big balances of flavors and stuff. So that’s what it is—making drinks that make people go “Whoa, that’s really fuckin’ cool.” So we come out with a different craft cocktail every Monday and we serve it until it runs out. Usually it sells out in a couple days, if not that night.

What does that process look like? Are you just making drinks at home all of the time? Some of these ingredients are things I imagine Sister doesn’t just have behind the bar regularly.

No, it’s literally like, I’ll wake up on Monday and go to Talin or El Super or anywhere I know they’ll have some random-ass fruit on sale. And then I’m walking down the aisles and see “Oh, there’s a shit ton of kiwi!” And then my mind just starts going: “What goes well with kiwi? Oh, kiwi-pineapple sounds good.” And then I’ll grab a bunch of kiwi and pineapple and bring it back here and make it work. … I’m really good at procrastinating, and what I’ve learned is that if I think about something too long, then my head is like “No, that won’t work, that won’t work.” So I have to work very in-the-moment. Going to the store, smelling the fruit, thinking of something I haven’t ever done before. This past week I did one with a snow pea rosemary simple syrup. I called it After the Rain because it was the day we got that big rain. (Find O’Brien’s recipe for this drink in the sidebar!) I just wanted something green and sprouty, and it was so refreshing and delicious. I had a couple people say, “this is my favorite one!” But a couple people say that every time.

Do you feel like there are certain flavors you gravitate towards?

I think I gravitate towards not just what I like, but what I think the masses will like. I’m rarely making something that’s super boozy-forward, just because that’s not really the clientele that comes in here. If I were to work back at Artichoke or at a smaller bar, where it’s more of you talking to the people a lot more than just serving the masses, that’s when I would do something a little more boozy-forward. I also lean towards things that are seasonal. So I always like using what’s fresh and what’s in season right then. What’s gonna taste good on this day? If it’s rainy or cold, I’m gonna make a hot drink. If it’s bright outside I wanna make something that makes me feel like I’m on vacation.

You’ve gotten a lot of great reception for your cocktails. How does that feel?

It makes me feel great, honestly. When I first moved back here I did my first competition and I was like, “I don’t know what I’m gonna do,”—but then I won. It was this huge confidence boost—“Oh, I actually do know what I’m doing!” And the every Monday thing has gotten me to where I can just try new things … it’s good for me, and for the bar.

You’ve won a ton of things since you’ve been here, like the 505 Food Fight.

Yeah, I’ve won that one twice. And then I’m gonna do this competition during the Cocktails & Culture week. (This happened last weekend, June 2 and 3! O’Brien won Third Place in the People’s Choice Competition.) We’re actually doing two of them. The first one we’re doing is called the Chef and Shaker event, where they send us a liquor, we make a dish with the liquor, I make a cocktail with the liquor to pair with the dish. It’s a Bloody Mary competition, and then right after that it’s going to be a “Chopped”-style type of deal with a mystery ingredient—which is like what I do every week! So I’m super pumped.

What’s it like working at Sister specifically?

It’s pretty fucking awesome. Great shows, great beer, great cocktails. This is my family here—we all call each other “sister.” It’s the best place I’ve ever worked, my boss is the best boss I’ve ever worked for. It’s funny, I made this promise to my friend when I moved out here: “I’ll go back for two years and then move back to Oakland.” And my friend told me, “You’d better not go down there and fall in love with somebody.” And at the time I was like, “Yeah girl, please.” But a year later I had to tell her “Sorry, I fell in love with a bar!”
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