Like most sommeliers, Derrick Westbrook grew his experience through working in restaurants and tasting rooms. At Chicago restaurants including Next and Elizabeth, he created extensive wine lists and his ideal food pairings. But these days, Westbrook, who now adds wine shop owner, wine culture curator, and Little League baseball coach to his title, is crafting a new kind of pairing experience with wine and music.

“Wine and jazz are very similar,” Westbrook says. Both disciplines have “rules,” but what makes a song or a glass more interesting is when those rules are broken — with intention. It’s that creativity, along with his desire to share and guide people through wine tasting in a fun and exciting way, that led Westbrook to start Samples and Samples, an event series showcasing both wine and music selections he curates. At each one-of-a-kind tasting, he selects a track and a remix or new version that samples the original song, and pairs each with a comparable wine. The result is an experience that’s as informative as it is entertaining: At this past summer’s event, Westbrook introduced guests, including this author, to variations of Sauvignon Blanc, from a low-alcohol wine to a richly textured wine from Marlborough — all while playing tracks by Kanye West, Curtis Mayfield, Justin Bieber, and the Fugees.

Westbrook’s approach to wine education is the ideal fit for his bubbly personality and professional background. Throughout his journey, from growing up in Tennessee (where he had his first sip of Champagne at the tender age of 8); to his first steps into the beverage industry at a small Italian restaurant in Birmingham, Ala., where he worked while attending college; and ultimately landing in Chicago where he honed his craft in tasting rooms, Westbrook has picked up the tools to build his vision for the future of wine.

Get the latest in beer, wine, and cocktail culture sent straight to your inbox.

In this interview with VinePair, Westbrook speaks about his love affair with wine and hip-hop, his favorite inspirational Jay-Z quotes, and tells us about his continuous effort to make wine more approachable for everyone — which he can now do at his own shop, Juice @ 1340.

1. When did you first fall in love with wine?

This reminds me of that “Brown Sugar” question, you know, “When did you fall in love with hip-hop?” So in the spirit of that, wine and I were dating for a while. You could say we had a little situationship thing going on. I’d see wine when it was convenient but was never really committed. I liked it and I enjoyed the time I spent but I wasn’t sure. For me, it was either wine or the nonprofit world, where I worked in education and policy change.

But I fell in love on this day: We were building the wine list for 57 Street Wines. It was my first time building a retail wine list and we had already tasted through tons of wines trying to build the massive list. There was this Riesling that I tried … Alsatian Riesling, and I’d known the producer and tasted their wines several times, but the rest of the team had not. Our distributor brought in their grand cru, and I told everyone they were going to love this wine. At that point we tasted it and there was dead silence. The room went quiet and I was like, “Yeah! That’s it.” That moment that I could share my love affair with someone else, that was the moment. Wine had always been a singular, selfish moment for me, and this was a moment that I could share it — and guide people into this world that I loved.

2. From growing up in Tennessee to college in Alabama, and then life in Chicago, how did each place help shape your interest in wine?

I left Tennessee at 18 to go to college, and up to that point my relationship with wine was nonexistent. But my first time ever having it was when I was 8, and the running joke is, that’s the day I became a somm [laughing]. When I got to Birmingham, that’s where the spark really happened. I was in college working at a small Italian restaurant building a wine list and had the opportunity to taste things. I knew that I could sell more glasses of wine than cocktails, even though cocktails were more expensive; and then I realized that learning the stories made it easier to sell bottles of wine. I liked that entrepreneurial feeling, and had found the space where I had entrepreneurship and something that fed my curiosity.

Soon after, I moved to Chicago. Birmingham had given me all the tools I needed and in Chi I found the lane, I learned how to talk about tastings and the experience of wine in a little bit longer format. In tasting rooms, people are curious and I had to learn how to explain the “why” and “how” that relates to the people who are drinking the wine.

When I ran my own beverage program and did a blinded tasting, and hit them all, that’s when I realized, “Oh, I’m built for this, like I’m good at this,” and that the studying [Westbrook is a certified sommelier] I’d done had paid off. Each city gave me something: Nashville built me and made me who I am as an individual and created that perspective. But in Birmingham, hustle and curiosity came together, which is during college, kind of indicative of what you want for that time in your life. And last but not least, Chi is where I found it as a career and realized that I was built for this and could do it.

3. What are some of the challenges of creating/hosting a wine event that is both approachable and informative?

I think it’s a new avenue, thinking about wine tastings in a way that’s not just a wine dinner. So the challenge is getting people to understand the concept, … to get them to think about wine as something that is inclusive and still important. One thing that I always think about is that wine and jazz are very similar. There are all these rules, but if you have a foundation of rules, just like with jazz, if you have a foundation with music, then you learn how to break them — and why you’re breaking them. And I want people to understand that. The biggest challenge is getting people to see it and try it for the first time, and making sure that I’m always learning and being exposed to new avenues, which is great because I’m always curious.

4. Can you talk a little about the idea behind Samples and Samples and how
you curate the playlists and corresponding wine lists?

It’s super interesting, sometimes it’s wine first, sometimes it’s music first. If I’m in a mood where I’m listening to the same type of music, I’ll stop and I realize there’s these tones, textures, and colors and notes that I keep bringing myself back to. Right now, I’ve been listening to a ton of Outkast. They have lots of contrasting elements. I find myself drinking wines that have very stark and contrasting flavors. So living life is kind of how I curate.

I’m also always listening to music –– be it in the shop [Juice @ 1340, where Westbrook is one of the owners] or in my headphones –– and when I’m drinking something the wine puts me in a mood. If I’m drinking big, complex wines, I want to listen to rappers who have tons of intricate lyrics, or I want to listen to chords and key changes. The experiences that I’m having in one area pushes me to the other, in an artistic sense. In a structural sense, it’s all about tones and notes. To me acidity equals horns and bass equals drums and tuba. I hear music in the flavors and textures that I taste wine, and I taste wine in the tones that I hear music. And I allow myself to be taken wherever the music or the wine takes me.

5. What is your favorite wine/music pairing right now?

One of my favorite pairings right now is Outkast and Chablis. There’s a record by Cautious Clay called “Karma and Friends” where he’s sampling the drums from the Outkast record “Elevators,” and that made me think about how now Outkast is the group that people sample — and that reminds me of Chardonnay and Chablis, particularly. Most people think that since it’s winter you should have something big and bold, but Chablis can have weight and texture. If it is influenced by a little bit of oak, it gets a nice heaviness. But you can also have Chablis that is light and crisp with damn near no oak and get these high-tone notes, and I think that’s like the beautiful juxtaposition between Andre 3000 and Big Boi of Outkast. It’s not about the Old World versus the New World, it’s about these two things together. And that’s the focus of this next capsule event.

6. Tell me about the upcoming event.

We’re doing Samples and Samples the day before my birthday. So it’s part celebration, where we’re putting out a capsule “Old World versus New World” featuring Outkast. For this event, I’m drilling down on a particular playlist and a particular field of wine. Old World wines, old-school music; New World wines and new-school music. Being able to be in both spaces at once is something that has been resonating with me from a personal and professional perspective.

7. How have your events changed since Covid-19?

I’ve been focused on intimacy and creating bodies of work around my events, which is something I’ve always wanted to do. Covid has made me more intentional about that.

8. Music and art have the ability to transcend adversities and bring people together. How do you feel this relates to breaking the stigmas of wine in various communities? Why is this important?

I think Jay-Z said it best when talking about race and music. He said, “The great thing about hip-hop is that if your favorite artist is Black then it’s really hard to have hate.” I think about that from a wine perspective: If the people who are talking about this thing you love don’t always look up to you, then I think it’s easier to become more accepting of different backgrounds or more proclivities. The more diverse group of people you have talking about beverage means more people can find identities that relate to them. We talk about the stigmas in various wine communities, but there’s also the stigma of availability –– be it price point or exclusivity. I always tell people, let’s start at taste, like, is it yummy? My job isn’t to change what you taste, my job is to give you the language to articulate what you’re tasting and experiencing. For me, it’s my way of placing my one grain of spiritual sand in a direction that gives people their identities back. The stigmas are prevalent but it’s nice that I get to debunk them in a way that’s informative but also fun and exciting. That’s why it’s important to me and that’s what I love the most about it.

9. In the future, how do you see diversity within the wine industry changing?

My job is to grow this thing as big as possible and then sneak someone else in the door with me. I think about it in terms of legacy; if I can create space for them, people who look like me and don’t look like me, then we can create a wine community that looks like our actual community. That’s the important but also fun part. Things are changing, slowly, and though we’ve come some distance there’s so much more to do.

10. Who in the wine world is inspiring you these days?

The mentors I’ve had, like Regine Rousseau, Brian Duncan, Andre Mack — I look up to them. They inspire me from a looking-up standpoint. But also, I’m really inspired by who’s next. I hate to think of myself as a mentor, but I like the kind of people in the wine industry who are behind me and interested in this as a career.

That, and even the kids who don’t even drink wine yet. For instance, I coach Little League baseball, and me being a sommelier and a baseball coach feels like I am giving them a different opportunity from a life perspective. And that is the place for me. That is most exciting, because they only know about the opportunities that they see. When I tell them I’m coming from work, and they say, “Oh, what do you do?” and I tell them — and they’re like, “What’s that?” — I think that’s fun that they see me as a regular person, they don’t see the wine stuff, the articles or the accolades. They just care about whether I can help them get better and can they win. It makes me want to work harder to have more free time to be around them. And I think that’s where the real inspiration comes from.

11. What advice would you give to up-and-coming somms?

Stay curious, and to be true and authentic to yourself and the way that you approach wine. As long as you’re in it to learn and find your voice, find someone else and try to follow. And make sure you love this, because it can be taxing and tiring [laughs]. It’s a tough industry, for sure.

12. What’s your next professional move?

I just opened a wine shop in June so for me it’s about growth and more ownership opportunities and creating more paths within the industry for people who want to do this. Trying to grow in the industry as much as possible. The guiding light is being able to sow seeds and watch those things grow.

This story is a part of VP Pro, our free platform and newsletter for drinks industry professionals, covering wine, beer, liquor, and beyond. Sign up for VP Pro now!