Growing up in the Bronx, Jermaine Stone planned to become a rapper. His visions of hip-hop stardom weren’t far-fetched: By his late teens, he had caught the attention of luminaries including LL Cool J and Chris Lighty, appeared on the radio, and even had a stint with the New York rap group Sporty Thievz.

To support his ambitions, Stone took a job packing boxes in a warehouse at the wine retailer Zachys. The role would alter the course of his life: A quick learner, Stone quickly rose through the ranks, learning the ins and outs of the wine industry and eventually becoming the company’s logistics manager, overseeing the transport of some $60 million in fine wine annually. About a decade later, he joined the wine and spirits brand Wally’s as the founding director of its auction arm in New York, where he honed his expertise. Over time, Stone came to realize that the focus of his work wasn’t resonating with his peers: He constantly saw his friends readily order a $600 bottle of champagne in a club, but refuse to pay $150 for a quality bottle of wine in a store. He wanted them to appreciate wine, too, and to show them that the drink, and the people behind it, could be anything but bland.

So in 2016, Stone founded Cru Luv Selections, a consulting and marketing firm with the aim of selling wine to his community. Its efforts ingeniously, and seamlessly, blend the worlds of fine wine with hip-hop, which Stone treats with equal reverence. His venerable knack for finding commonalities between the two domains shines in his company’s output, which includes the Wine and Hip-Hop podcast, on which Stone interviews a musician or a wine professional about a song or bottle of wine they choose, and the pairing he makes for their selection. Select video footage from the recordings feature on Wine and Hip-Hop TV, a YouTube channel that builds on the podcast with special segments such as “Tasting Notes From The Streets,” which sees Stone pairing some of his favorite foods with beverages from all over the world. (Previous episodes have coupled chicken and waffles with Zardetto Prosecco, and Jamaican beef patties with Spätburgunder, a German Pinot Noir.) There’s also the Wine and Hip-Hop Wine Club, which sends subscribers a selection of wines to try while listening to a dedicated playlist, and invites them to join Stone on Zoom to discuss the notes of both. Throughout, Stone’s insights—lucid, knowledgeable, casual, and cool—get to the core of both wine and music, and lay out what ties them together in unexpected ways.

We recently asked Stone to put together for us a playlist of his favorite hip-hop songs, and make a wine pairing for each. Below, he walks us through the ideas behind the sets.

Listen to Stone’s “Wine and Hip-Hop Playlist” on Spotify.

“What I Look Like” by Sporty Thievz, paired with Bandol Tempier Rosé 2019

“When I was in high school, this song was a hood classic. Sporty Thievz had that song ‘No Pigeons,’ a parody of TLC’s ‘No Scrubs.’ It challenges gender roles, which at the time was a radical idea. The group was seen as very misogynistic, and if you choose to look at their music that way, it’s easy to feel that. Nowadays, however, gender roles have changed a lot. There’s a ton of complexity within them. As a concept and at face value, you wouldn’t think so. That reminds me of rosé as a category, even though some display great complexity. If you’re drinking rosé, you might as well go Bandol. I feel like rosé deserves a bit more credit in the same ways that this song and these artists do.”

“Homecoming” by Kanye West, paired with Zardetto Long Charmat

“Kanye West put this song out twice. One is a version with Chris Martin on the Graduation album, which was cool. But the original version, featuring John Legend, is insane. It came out way back in the day before Kanye was signed to Roc-A-Fella Records, when he was still doing a lot of his music independently. At first, it sounds like he’s talking about this girl that he met really young, what they went through, and his coming back. But really, it’s a love song for the city of Chicago.

Zardetto is known for the hidden messages on its labels, which you peel back to reveal an Italian phrase translated into English. There are two meanings, similar to the way that the song has two meanings. The drink is made from one hundred percent upper-echelon glera, which we have to pair a billionaire’s songs with.”

“Gnat” by Eminem, paired with Auguste Clape Cuvee Renaissance Cornas 2019

“This is one of the best lyrical performances of all time of any audio recording ever. It’s like a bicycle, with a lot of different spokes and some really cool tongue-in-cheek metaphors. Eminem says two metaphors in one line, and does that like two hundred times. That is not an exaggeration.

The Auguste Clape Cuvee Renaissance Cornas 2019 is similarly dense, with a long finish. The sip is gone, but you’re still savoring it. It continues to evolve in your mouth, like these Eminem lyrics. You get his lines like five for six seconds after they’re sung.”

“100 Bars” by Canibus, paired with 1998 D’Oliveiras Bual Vintage Madeira

“This is a very complex rhyme: ‘My brainwaves on an encephalograph show that I’m stark-ravin’ mad’—you have to know what an encephalograph is to appreciate that line. It’s also a long song—six minutes or so—and there’s no hook, nothing. It’s just raw and aggressive. I paired it with the ’98 D’Oliveiras Madeira, because it’s going to last forever. Like a song that might put you on your ass, this wine might put you on your ass. You can’t drink the whole thing by yourself.”

“Royal Flush” by Big Boi featuring Raekwon and André 3000, paired with 2008 Domaine Dujac Clos de la Roche Grand Cru

“When some people think about complexity, they think of the importance of balance. Although André 3000 has a lot of complex metaphors in this song, he was also concentrating on flow. His lyrics are spaced out, confident, and easy to get, but at the same time, really meaningful: the definition of perfect complexity. I had to pair that with Dujac Clos Grand Cru. It’s a perfect balance, everything that you want out of a wine. If I had to pick one last wine to drink, this would be it.”

“F.I.F.A.” by Pusha T, paired with Krug 2002 Vintage Brut

“In Pusha T’s lyrics, he doesn’t miss a single word. On ‘F.I.F.A.,’ I especially like that he connected his tone of voice with everything else he was doing. It’s an extremely visual song. For me, champagne is very visual, very explosive. I see fireworks. Krug is one of my favorites. It’s super accessible.”

“Another Brick Please” by Fred the Godson featuring Jaquae, paired with Chateau d’Yquem Sauternes No. 2

“Fred the Godson was a personal friend. He was a hip-hop legend, and someone who did not get his due as a lyricist. The double entendres he used were fun, because they’re so basic that you would just never think of them. ‘Like cheap ass seats, everybody he knows bleeds.’ It can be a little too good when there’s so many back-to-back.

As for the pairing, we don’t really buy 750s of Sauternes, in all honesty. It’s a half-bottle type of thing, a restrained serving that mirrors how Fred’s lyrics might be best consumed. The drink has amazing complexity and a beautiful acidity that you can get with a wine with this level of sweetness.”