E-40 and Ja Rule got real about taking control of the liquor industry’s love affair with hip-hop.

IN 1996, EARL STEVENS, the artist commonly known by his serving-size-related nom de plume, E-40, was paid $60,000, the most money he had ever received for a single day of work. The Vallejo, California, native drove to San Francisco to record a jingle and shoot a commercial for the malt liquor brand St. Ides, produced by the SF-based brewer McKenzie River Corporation.

Since the late ’80s, the company had (somewhat controversially) made a name for itself by branding its cheap, high-ABV malt liquor in a splashy campaign that was art directed by the artist and producer DJ Pooh—paying rappers across the country including but not limited to Notorious B.I.G., the Wu-Tang Clan, Ice Cube, Rakim, Kool G Rap, and 2Pac to do precisely what E-40 was doing: make a short song and video to be played on radio and television stations.

The relationship between rap and St. Ides was somewhat symbiotic. The artist got the check and the exposure that came with selling product for the retailer, which mined rap’s countercultural cool as well as the artist’s fan base as a demographic grower. “In the ’90s, it wasn’t too many resources at all for us, bro,” 40 recalls in a recent conversation with TASTE, looking back on the opportunity. “No one threw us a rope, you know what I mean? We had to make a way out of no way. I’m here because I held on like a hubcap to a tire in the fast lane.… We had to build shit from the ground up.”

Twenty-nine years later, E-40 is a player in his own right in the $645 billion a year spirits industry. Launched in 2013, his company, Earl Stevens Selections, features a deep roster of products—“like five brands and probably 26 SKUs,” as 40 describes it—selling everything from tequila to sparkling wines in flavors like watermelon and cotton candy, all currently distributed in 41 states.

Earl Stevens Selections is hardly alone. Many musicians have gotten into the alcoholic beverage industry, pitching everything from canned cocktails to special-edition cognacs that retail for thousands of dollars.

Beyoncé just launched her whiskey SirDavis on the cover of GQ; Cardi B sells a vodka-infused whipped cream called Whipshots, and Dr. Dre and Snoop Dogg literally sell Gin & Juice. The relationship between rap and the alcohol industry has come a long way from rappers serving as mascots for bodega rotgut. How we got here is a story of an industry evolving and maturing, of artists rejecting the institutional power structure, and recognizing, then taking ownership of their tremendous financial might.

RAP IS the most biographical and conversant form of American popular music. Most rappers’ lives and habits are knowable and relatable through their lyrics in a way those of folk singers and punks could never be. Whether it’s Common endorsing Assata Shakur through his poetry or E-40 rapping about getting bent on a particular brand of wine, the references and the cultural ephemera that creep into rhymes have always mattered and served as a blueprint for the young fans who look up to the artist as a role model: what to read, what kind of car to drive, how to dress, what to eat, where to drink, what to drink, how to live.

As such, rappers occupy the liminal space that rap writer and historian Dan Charnas has described as “artist merchants” in his seminal book about the industry of rap, 2010’s The Big Payback. “Hip-hop has a natural affinity for capitalism and branding, and it’s very at home in that area. It doesn’t consider consumerism anathema to artistry, as is the case in other genres,” Charnas tells me.

But there were few instances of corporate America catching on to this potential before St. Ides. Malt liquor is essentially fortified beer that tastes skunked and curdled even when fresh-cracked and ice cold, the backwash of already bad domestic beer often served in a family-size container. St. Ides’s 8.2% alcohol by volume doesn’t seem as gaudy today, in a world of normalized Belgians and tripels with percentages that can reach the double digits, but through the ’70s, ’80s, and ’90s, it was seen as a low-cost, high-efficiency getting-fucked-up delivery system, making it an intuitive market for the underserved, uncatered to people who have to get drunk on a budget.

You can follow the nightmarish history of the role race has played in socioeconomic status and redlining in America and understand why using Black culture as a vessel to market to inner cities made good business sense for a malt liquor brewing company.

“Well before hip-hop, malt liquor companies established Black Americans, especially Black men, as their primary and, I would say, only real target audience,” Charnas says. “In the ’70s, Soul Train would air Colt 45 commercials, and Billy Dee Williams was very much a part of that.” By the early ’90s, the G. Heileman Brewing Company reported that 75% of the customer base for its malt liquor, Colt 45, was Black. So malt liquor is both bad and bad for you, and from the outside, the politics look terrible.

Labeling the white-owned St. Ides’s marketing strategy as exploitative is easy, but it’s not fully telling the story from the point of view of the rap industry. “It was a big deal for rappers to be in a St. Ides commercial at the time. If you was in one of those commercials, that made you the shit,” E-40 says.

For whatever issues critics back then (or today) may have had with St. Ides and the proposition of pitching malt liquor, these were the branding opportunities available to rappers. Even as they profited off rapper endorsements, brands like Timberland vocally distanced themselves from their Black clientele as the US government scapegoated hip-hop for the havoc Reaganomics had wrought on Black communities, attempting to legislate the “societal ill” via racist paternalism.

At the time, rappers couldn’t even endorse brands in their own videos, as outlets like MTV would blur any visible logos and labels because it was considered free advertising. It was all part of a decades-long attempt by mainstream American institutions to suppress hip-hop. “It’s a class privilege to think of art and commerce as separate. Hip-hop had to be able to sell itself, and rappers had to be able to be entrepreneurs in order to survive. So they found a way,” Charnas says. And this was rap’s dilemma. Whenever an opportunity to break into the mainstream or make real money presented itself, there was a concerted effort by the state to cancel it.

It should come as no surprise that throughout the ’90s, St. Ides faced several fines and forced shutdowns at the hands of the New York State attorney general and the federal Bureau of Alcohol, Tobacco, and Firearms. Infractions included an ad featuring Ice Cube lyrics that was interpreted as suggesting St. Ides “increases sexual prowess,” “glamorizing gang violence and promoting sex,” and “predatory marketing practices” allegedly targeting minors in advertising—in other words, using rap music to sell its product.

These crackdowns were a motivating factor in McKenzie River deciding to discontinue the brand in 1998. After a round of corporate hot potato, St. Ides ended up in the hands of the Pabst Brewing Company, which still produces it today.

In its wake, the marketing opportunities around rap artists exploded, along with record sales. Hip-hop became a billion-dollar industry, thanks to a dawning acceptance of how much potential revenue was out there beyond “just” the music. Rappers became models and makers of clothing; they sold cars, kicks, magazines, fast food, and soda in addition to booze. The bottles artists began to rap about leveled up commensurately as a new age of conspicuous consumption and luxury materialism crept into lyrics.

The 40s were gone, and in their stead came high-end imports. An exemplar is 2Pac’s 1996 song “Thug Passion,” dedicated to a fifty-fifty sparkling cocktail of his own design that was one part Alizè, a passion-fruit-flavored French vodka, and one part Cristal, a 150-year-old Champagne from the winemaker Louis Roederer.

It is fitting that the big bang for rapper-booze entrepreneurship was a perfect illustration of the blatant disrespect—if not outright contempt—major corporations had for the hip-hop community and the millions of dollars hip-hop fans pump into their companies annually. In 2006, Frédéric Rouzaud, the president of Louis Roederer, was asked whether hip-hop’s attraction to his product could be detrimental to the brand. “That’s a good question, but what can we do? We can’t forbid people from buying it. I’m sure Dom Pérignon or Krug would be delighted to have their business,” he said.

It was an expensive sound bite. The quote made headlines, and Jay-Z, who had spent years promoting Cristal in his raps for free, publicly boycotted the brand. The lead single for his next album, the 2006 “post-retirement” comeback Kingdom Come, is “Show Me What You Got,” which operates less as a music video than a four-minute soft launch for a then obscure Champagne called Armand de Brignac (which Jay-Z was secretly a 50% partner in with Sovereign Brand CEO Brett Berish, who was instrumental in putting rappers front and center in the marketing and ownership of liquor brands, and today owns the Luc Belaire sparkling wine brand with Rick Ross, and Bumbu Rum with Lil Wayne, among other ventures.

Jay-Z would buy out Sovereign’s share in Ace of Spades and D’ussee in 2014 to own both outright ) and its signature chrome bottle with a spade emblem at its heart. It was the dawn of a new age.   

André Hueston Mack was the beverage director at Thomas Keller’s Time Warner Center jewel box Per Se before he struck out on his own to become a renowned winemaker, media personality, and restaurateur. He’s also Black in an industry where that was once a rarity, and he has a unique perspective on how hip-hop has shaped alcohol culture. “Rappers were already dictating what people would drink when they go out to bars, clubs, restaurants. Lil’ Kim rapped about moscato, and all of a sudden Sutter Home started making more moscato than it did white zinfandel, so it makes sense that rappers got into the supply side,” Mack says.

Before Armand de Brignac, Jay-Z had Armadale, a Scottish vodka distributed by Roc-A-Fella Records that dissolved when his partnership with mogul producer Damon Dash did—but in motivating the rapper to get in on the high-end wine market, Rouzaud had inadvertently created a monster. Armand de Brignac and Jay-Z’s cognac, D’Ussé, became behemoths. In 2021, Jay-Z sold half his stake in the brands to the luxury retailer LVMH (which produces, among other bottles, Dom Pérignon, Moët & Chandon, and Hennessy) for over $600 million, or more than 10,000 times what St. Ides paid E-40 for an ad. In the mid-aughts, many rappers followed Shawn Carter’s lead.

The former music executive and current Metropolitan Detention Center inmate Sean Combs went into business with Diageo, turning its struggling vodka brand Cîroc into a global label shipping millions of cases a year. Ludacris launched a cognac in 2009. In 2013, Nicki Minaj became a partner in MYX Fusions, a fruit-infused Moscato brand. It was the same year E-40 founded Interactions and Transactions, a 100% Black-owned S Corp whose goal was to begin developing and producing alcohol brands.

Today owning and selling your own booze has become a standard article of rap stardom, or even mid-level rap popularity. For some rappers, it’s a vanity project to sound like the business mavens they advertise themselves as in their raps and a way to shoot for some of the demographic St. Ides once dominated with similarly shitty swill. For others, it’s another creative outlet, a chance for artists to explore and develop a passion project—a labor of love, putting the wine or spirit they’ve dreamt about into the world.

“WINE IS ART to a winemaker, so it’s just like asking an artist what their personal connection is to their work. It’s everything. The whole idea is that if you’re in control, you wanna make the wine that you would like to drink, so along with the diversity comes a lot more range in the styles of wines that are available,” André Mack says. Ja Rule had always been a basic-ass pinot grigio guy. But some circumstances, some meals, demand body and heft, so the Queens-born MC branched out. “I was trying to find a red I enjoyed and couldn’t really find one, so I decided to make one that was to my liking, a red that was more for the guy who may not be a wine connoisseur but wants to enjoy a glass with steak,” Ja Rule tells TASTE.

His solution? He got in touch with Wines That Rock, a novelty producer that historically made collectibles like Star Trek wines featuring expressions like their Risan Picard Sauvignon Blanc, sold in a bottle that looks like a beaker with what I think is Klingon written down its label. But Ja took the assignment seriously on what he describes as a joint venture with the brand, linking up with Ross Reedy, an established winemaker with a global pedigree who was born and raised in the Alexander Valley, in northern California’s wine country. They collaborated to produce 500 bottles of Red Rose Cabernet Sauvignon, which currently retails on the Wines That Rock site for $100 a bottle.

That product is yet another example of what Mack is saying: why representation is important in any field. Few winemakers have Ja’s life experience or interests, so unsurprisingly, with the tools at hand, he ended up creating the ideal accessible Cali Cab for, oh, let’s say, a young artist from Hollis who has recently become successful and wants to begin his wine journey, moving from crushable whites to his first hammer at the entry level of taste if not price.

Rather than some oak bomb a few years from hitting its drinking window that you drop $200 on and need to age for three years, then let breathe for two hours before you can have a glass, Ja custom engineered a pop-and-pour, lush and slutty juice bomb that hews closer to its notes of stone fruit and berries than its mild tannic structure. “It was a really pleasant surprise,” he says. “More than I imagined a red wine could be. I’m really happy with the product.” So much so that he’s getting back in the game with Amber & Opal, an organic elevated botanical honey whiskey, working its way to shelves as we speak.

Mack sees the development as a cultural shift. “Today wine is way more diverse. There are more people of color in the industry than there were five, ten, twenty years ago. People are seeing wine being consumed by people that look like them, being talked about by people that they admire, and the long-tail effect of that is more people than ever, from all walks of life, coming to the space.” He continues: “If you don’t see anybody that looks like you doing something, you don’t think it’s for you, and I think by democratizing the wine world, by opening all of this stuff, you add different experiences, which leads to different expressions.”

This explains why this shit matters. It’s not just a way for artists to capitalize off their name recognition; it’s another form of artistic expression, a marriage of personal and financial interests. For Alison Roman, knowing your brand means a popular Substack and a cookbook selling simple anchovy pasta recipes. For E-40, it means something else. The rapper’s on-wax booze advocacy dates back to 1993’s “Carlos Rossi” (with the mild typo hilariously left in) off his studio debut Federal, an anthem dedicated to the purveyor of four-liter jugs of cheap juice.

“Rapping about wine and spirits, that was one of my main things, even before I thought I was going to be able to make my own. Carlo Rossi is what we used to drink before studio sessions. Pay eight bucks, get a big-ass jug, and go hard.” He reflects. “Coming from Vallejo, near Napa, it only makes sense for me to be a wine connoisseur.”

A FEW WEEKS AGO, I went to Eclectic Wine & Liquor, a retail shop in Bed-Stuy on Fulton Street off Nostrand Avenue, one of the few places I could readily find on Google that carries Earl Stevens Selections (the Prosecco, Moscato, Sweet Red, and Sparkling Cotton Candy, which is currently out of stock but I’ve been told is being reordered). When I got there, faded life-size cardboard cutouts of Rick Ross and Brandy holding their various products greeted me behind the floor-to-ceiling plate glass window, and it reflected the offerings within, carrying artist brands like Jay-Z’s cognac and Lil Wayne’s rum.

When I asked about bringing in these products, the shop’s proprietor—who requested not to be named in this piece ostensibly promoting his establishment, because Brooklyn—told me he takes a pragmatic view of stocking his shelves. “My inventory is built based on what the community asks for. I’ll take a shot on selling something if I get a request, maybe because some rapper is talking about it, but to see if it’s this one person or something the neighborhood wants. I think for certain artists the product certainly helps. Beyoncé launched a whiskey, and it sold out right away, so I’d bring it in again. But as a rule, if it sells, we keep it. If it doesn’t, we won’t.”

The proprietor shared that these products tend to have their moments that mirror the success of the artist attached to them. In other words, slapping your name on a bottle can bring short-term success based on your fame as an artist, but building a lasting product takes good taste, good-faith engagement, discipline, and smart business decisions.

Ja Rule never made a St. Ides commercial, but when I asked him about the journey of rap and rappers from spokemodels to owners, he compared it to the other industry that rap began working for, then slowly took equity in: streetwear. Companies such as Timberland, Tommy Hilfiger, and Ralph Lauren saw their popularity and sales soar in the ’90s when rappers began rocking their apparel in videos and eventually print and TV ads. A wave of rapper-owned clothing labels soon followed, with strings attached. “Everybody was doing clothing deals at the time, and you know it’s basically 8% deals. I couldn’t understand it. You’re telling me I’m going to own 8% of my company and you guys have the other fucking 92%? So I started my own company, and [Recently deceased producer and Murda Inc. Records founder Irv Gotti and I]  owned 100% of it,” Ja says.

“I was trying to find a red I enjoyed and couldn’t really find one, so I decided to make one that was to my liking, a red that was more for the guy who may not be a wine connoisseur but wants to enjoy a glass with steak.”  — Ja Rule

But what he quickly learned is that there are advantages to entering into an existing framework, with all the sourcing, labor, distribution, and institutional knowledge necessary to navigate the variable rules and regulations of sales from state to state, handled by a corporation that has spent decades learning and streamlining the process.

It speaks to the education rap writ large has gone through, developing networks and acquiring resources, both financial and structural, and why the rapper-owned liquor explosion has slowed down somewhat. The novelty has worn off, and the reality that everyone can’t be Jay-Z and every product can’t be Ace of Spades has dawned on the industry. Entrepreneurial empowerment and the artistic freedom that ownership affords a creative person come at a price. “If you have a vision for something, you should have ownership of it. But in some cases, you can have 100% of nothing, or 10% of something that is very, very valuable. You have to pick and choose your spots for equity,” as Ja puts it.

“I’m independent because I’ve been doing it all my life. It’s a new product, same hustle,” E-40 says. He recalls building his wine and spirits brand like he used to sell his music, hand to hand. He once sold mixtapes out of liquor stores in Vallejo. Decades later, he started a label selling cases of wine direct to consumers on the internet. “I got me a distribution deal with records just like I got a distribution deal with Southern Glazer’s Wine & Spirits,” he says.

When we spoke, I asked E-40 to walk me through the research and development process, expecting him to share some colorful stories about what tasting and developing new products for the market is like. Instead he began burying me in arcane legalese, delving into trademarking recipes, getting artwork designed and approved, and the minutiae of dealing with the California Department of Alcoholic Beverage Control, like a persnickety, detail-oriented patent clerk. He’s an artist-entrepreneur who made the journey from pitchman to brand ambassador to brand owner over decades, and he doesn’t pay his business lip service. He has truly invested in learning and growing his empire.

Remember that we are discussing a group of people who became famous as writers, musicians, and artists. The pursuit of craven capitalism and the all-encompassing high stress and long hours of entrepreneurship demands are not a natural fit for all of them. The point is not that every rapper should have a brand but that, at last, we’ve reached a point where artists who are interested in and suited for brand ownership have the resources to pursue it. Dan Charnas tells me, “Once something becomes mainstreamed, there’s an easier route. Corporations will say, ‘You take less money, and we do most of the work, and we plug you into our system.’ It’s the mainstreaming of hip-hop that has made the incentive to become entrepreneurs less urgent.”

But for those chosen few, it’s fucking cool—an invigorating challenge with the potential for huge rewards that in some cases have created generational wealth and minted a new class of Black billionaires. A rapper can now reach the same stratosphere as the Gwyneths and Oprahs and Ryans of the celebrity brand industry, a level that was closed to them in all respects besides exploitation for generations.

It’s a particular stripe of rarefied progress that is easy to be cynical about, but for the artists of the ’80s and ’90s, who only had malt liquor commercials to look forward to as the pinnacle of their commercial (and often financial) success as spokespeople, it’s progress. “We were fighting for a world in which good things can happen, which meant we were fighting for two things—access and equity—and both happened,” Charnas says. André Mack sees it as more than a way for a select few to enrich themselves but a net societal good. “Celebrity wine culture is helping wine become a part of popular culture. Wine is a condiment, to food and to life, and rappers getting into the industry are helping people realize that,” he says.

I ask Ja Rule why he felt that the risk and all the work was worth it to produce an expensive bottle of wine with his name on it—why it’s more fun and more meaningful to sell your own shit rather than stump for someone else and take the easy money. He pauses, then says, “Look, I’ve always been the artist to say to myself, I would rather create something, do it, and own it, versus somebody pimping me out.”