AI Says These Are the Best Bay Area Rap Albums of All Time

The headlines are all about AI these days — most recently with an “AI Drake” song and a Biggie version of Nas’ “NY State of Mind.” Both have gone viral and reintroduced a running debate about the dangers and legal implications of artificial intelligence. One thing is painfully clear: it’s not going away anytime soon.

I grew up along Highway 101, on the northern edge of Silicon Valley — just one exit away from where Google’s Mountain View campus would eventually sprout, and only a few miles from Facebook’s headquarters in East Palo Alto. I won’t lie — my lifelong proximity to every tech trend has made me skeptical, if not resistant, to the latest technologies.

So when my wife started messing around with OpenAI’s controversial ChatGPT on her new phone, I surprised myself when I asked her to engage the hyper-algorithmic platform to answer what I thought was a basic question:

“What are the best Bay Area rap albums?”

Deep down, I was curious if the decades I’d spent digging through crates, listening to cassettes, burning CDs, freestyling in the back of parked cars and on corners, doing graffiti, attending hip-hop events, reading about the subject, taking college courses about the genre, discussing the craft with artists and religiously streaming the newest talents on today’s apps would compare to the almighty knowledge of ChatGPT.

Here’s what it spit out.

Ironically, A.I. approves of funky homosapiens

Before listing what it deemed the best 10 Bay Area albums, ChatGPT opened with a preamble: “The San Francisco Bay Area has been an important hub for hip hop since the early days of the genre, and has produced some of the most innovative and influential rap albums of all time.” Truer words have never been typed by a non-corporeal cloud.

Though the list in its entirety had some disastrous flubs (more on those later), I was impressed by the specificity of the suggestions. This isn’t just a beginner’s list that any bozo might posit at trivia night in a desperate attempt to appear knowledgeable. It actually offers some gems, worthy of consideration for any true Bay Area hip-hop head.

Here are the highlights from OpenAI’s suggestions, as they randomly populated my screen:

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‘93 Til Infinity by Souls of Mischief. Classic record, no pushback here.

Deltron 3030 by Deltron 3030. To be fair, I’m not sure this is considered a strictly “Bay Area rap” album. It’s a collaboration between two Bay Area legends and a Canadian, and is as much a science fiction odyssey as it is rap. But sure. We’ll toss it in.

The Coup by The Coup. Of all the Coup’s releases, ChatGPT picked this obscure, cassette-only 1991 EP — technically not an album — released decades before the group’s frontman and Town activist, Boots Riley, pursued an alternative career as a dope filmmaker who premiered his latest script, I’m A Virgo, at this year’s SFFILM.

Hyphy Hitz. A sweep-kick compilation of Bay Area hyphy anthems featuring The Federation, Keak Da Sneak and The Team. Looks like it came from the bargain bin at Walmart.

The Jacka Presents: The A.R. Street Album by The Jacka. A 2012 label showcase that features Bay Area mainstays like Husalah and Fed-X. An odd selection, though ChatGPT did respectfully note Jacka’s passing in 2015.

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In A Major Way by E-40. My personal favorite here, and still among the most-played CDs in my outdated stick-shift vehicle to this day. (I told you, I don’t fully trust automation.)

Overall: a couple miscalculations, but it represents the diversity of the region’s soundscape. You get a mandatory Hyphy compilation from the early aughts; a bit of darkly synthesized mobb music from the early ’90s; a taste of the East Bay’s weird, underground flavors; political credos from a group of revolutionaries; and the soundtrack of a street legend, murdered in his prime. That’s a solid encapsulation of what makes Bay Area rap so prolific and multifaceted.

So far, if you didn’t know that a non-human compiled this list, it probably wouldn’t arouse any suspicion that it was churned out by a computer. What would absolutely be a red flag, though, is the remaining four albums.

A.I. inevitably misinterprets and misinforms

Anyone worth their salt in hip-hop knows that regional pride is one of the most beautiful and sacred aspects of the culture. You would never catch a New York-bred rapper repping Chicago, and you wouldn’t label a Southern rapper’s music as representative of the Midwestern experience. It’s practically hip-hop law to flex your area code; to misinterpret or overlook these regional distinctions is definitely a violation of hip-hop’s territorial ethos.

So to put Public Enemy (a pioneering East Coast group), Aceyalone (a distinguished L.A. lyricist recently nominated for a Grammy), Dr. Dre (is there anyone, besides Snoop, who is more representative of L.A.?), and Arrested Development (an Atlanta-bred collective) on a Bay Area rap list is alarmingly off-base.

To the credit of ChatGPT, it provides context for its choices, and that’s where its failures got especially interesting.  It’s where the cultural layers became nuanced, and where ChatGPT — whose parent company, OpenAI, is based in San Francisco — failed to distinguish literal information from regional common sense.

According to the bot’s Ultron-esque index, Public Enemy’s Fear of a Black Planet was recorded in Sausalito; Aceyalone’s All Balls Don’t Bounce was recorded in Berkeley; Dr. Dre’s The Chronic features “Bay Area artists like Too $hort, MC Ren and Eazy-E”; and Arrested Developments’ 3 Years, 5 Months and 2 Days in the Life Of… was recorded in San Francisco.

And none of that is true.

Public Enemy recorded Black Planet at Green Street Recording Studios in New York’s SoHo. Aceyalone did his thing at Kitchen Sync Studios in Hollywood. Dr. Dre and his crew of Compton (not Bay Area) rappers laid it down at Death Row Studios in Los Angeles, while Too $hort doesn’t appear anywhere on the project. And Arrested Development, the group that always reps the South? They recorded their debut in, you guessed it, the South.

You’re maybe wondering how the hell ChatGPT got it that wrong: In what parallel multiverse does Long Island become Sausalito? Why would a group that helped put ATL on the map suddenly switch coasts and record in Frisco?

And even if these albums had been recorded in the Bay, would they be considered foundational to the legacy of Bay Area rap, and representative of our region’s unique vibe? I’d vote no.

My weekend dabbles with ChatGPT — the highly-touted, highly-automated information generator that can’t yet distinguish cultural fabrics because it is, obviously, lacking a sensory connection to our world — once again reminded me what I’d already sensed. Tech is cool, but it will never be able to replace the grains of our fullest, most intuitive humanity.

Maybe that’s because ChatGPT has never danced to Mac Dre or The Whole Damn Yey at a house party in Oakland or San Jose. And let’s hope it never does.