We were halfway home from the Warriors game when E-40 told me that he was perkin’. “You know what perkin’ means?” he asked, from the back seat of the chauffeured SUV. Half turned around in the front, I told him that I did: he meant that he was drunk. This is one of countless terms you rarely hear outside of the Bay Area, but which you frequently hear on E-40’s records, along with a fleet of others that are more or less unique to his vocabulary, including: turtle (weed), gouda (money), undersmell (understand), elroys (police), and botch (bitch). He paused, then he used one I hadn’t heard before. “I ain’t gonna lie,” he said. “I’m a little warped.”

It had been a big night. We had our first drink outside the VIP entrance to Oracle Arena, standing by the metal detectors. E-40 goes to about half of the Warriors home games, he always sits courtside — usually with his wife, Tracey — and he likes to drink Cape Codders while he’s there. In that respect, this night was quite typical: Tracey, his partner of 31 years, was his date, and, for the 45-minute ride over from his home in Danville, he brought a handle of Tito’s vodka with red Solo cups perched on the spout and a jug of cranberry juice. He’d intended to mix up some drinks as we made our way to Oakland, but, he explained as we pulled into the stadium parking lot, I had distracted him by asking too many questions. So he made cocktails for the three of us as we prepared to hop out.

We exited, drinks in hand, to a chorus of admiration (“You enjoying the fruits of your labor?”) and aspiration (“Lemme sing the hook, bruh!”) from the valet guys. It’s hard to overstate how beloved E-40 is in the Bay Area. Just about everyone we encountered from the parking lot to the interior of the arena — children, concessions employees, the guys checking tickets — seemed to be fans. But it turns out that even famous rappers can be compelled to down a large beverage before clearing security.

He was wearing a black Panama hat low on his brow and a black hoodie emblazoned with the cover art from his most beloved album, 1995’s In a Major Way, where he’s imprisoned within the face of a Rolex watch, standing over a stove littered with drug paraphernalia, peering back at the viewer over his shades. As we made our way through the bowels of the stadium toward the bar, I could finally see that there was an entire paragraph of explanatory text on the back: “In a Major Way was released March 14th 1995 on Sick Wid It/Jive Records, and is E-40’s first certified platinum solo album. A true classic in every sense of the word, In a Major Way embodies an era, with vicious wordplay and beats that slap to this day.”

That E-40’s most celebrated record requires, in his mind, an entire paragraph of explanatory text is telling of both his longevity — now about 22 years old, the album predates many of his listeners — and his status in rap music: perpetually, and frustratingly, circling around the lip of massive mainstream popularity, without ever quite dropping in. It was telling in another way, too. During halftime, over a plate of complimentary nachos and a gargantuan vodka-cran — he drinks them out of Pepsi fountain cups — E-40 explained that the sweatshirt was going on sale in his online store the following day, and he had been wearing it courtside, taking advantage of his incidental TV appearances, because he figured it’d help move a few units.

Plenty of rappers make a fortune in music, then roleplay as skilled entrepreneurs. Some do so successfully, but few had to become savvy businessmen in order to become famous. Not so with E-40. Before he ever met with a major label, he had built his own small empire in the Bay Area, selling his own tapes independently. And since then, he’s devoted his spare time to a number of colorful side-hustles: a couple franchise restaurants, a nightclub in San Jose, real-estate flipping, and, most recently, his own malt liquor, wine, and pre-made cocktail.

E-40’s hardwood perch at the Warriors games puts him cheek-to-jowl with the Silicon Valley elite that have come to radically reshape the Bay Area over the last decade and a half. Though E-40 might be a few times cooler than those guys, he projects a similar self-image, that of a cunning and eccentric entrepreneur who found success by exploiting weaknesses in sclerotic systems. But Silicon Valley’s many successes have complicated E-40’s. Technology has transformed the music industry in the way it has transformed so many industries: the barriers to entry are gone, but there seem to be fewer winners, the spoils accruing to the few at the expense of the many.