Caleborate’s already been recognized at least 20 times today, here on Telegraph Avenue. It’s become a running joke: as soon as he starts telling me something important, the short, eloquent rapper gets interrupted, usually by girls, and asked for a selfie. When he makes the turn to Dwight Way, bumping into a kid in glasses, a striped shirt and backpack, he offers a polite apology—”Oh, sorry, man.”

“Wait, wait!” says the kid, popping his earbuds out and fishing for his phone. He holds up the screen to show what he’d been listening to, at that very moment: Caleborate’s own album 1993—one of the best, if not the best, Bay Area rap albums of the year.

The album’s only been out for three days, but judging by the hordes of fans on the street here in Berkeley, you’d think it was already platinum. The two share a laugh and a requisite photo, and the kid echoes just about everyone else who’s stopped the 23-year-old rapper today to give ups to 1993.

Fame in the East Bay is a strange ladder, with different rungs. For every Metallica, Counting Crows or Green Day who made it to the top, there are a hundred tiers in Caleborate’s field—Mystik Journeymen or Hieroglyphics or Living Legends, rap artists who once made a name for themselves by selling tapes on this very street.

As Caleborate stands in front of Rasputin Music, dreaming of the day the store displays his album art in its sidewalk gallery (“that’s when I’ll know I’ve made it,” he says), I notice a tall figure in mottled dreadlocks and a goatee walking toward us. He’s fiftysomething, pudgy, wearing a Gram Parsons T-shirt and carrying a tote bag.

I do a double-take, and then it hits me: it’s Adam Duritz, the lead singer for Counting Crows.

I turn and watch Duritz walk Telegraph, past hordes of uninterested young students, down the block and around the corner. Nobody recognizes him. Nobody. Meanwhile, yet another fan stops to take a photo with Caleborate, this young, hungry rapper from Berkeley who hasn’t made it yet.

If Caleborate set out to make an album designed to appeal to older rap fans raised on Eric B. & Rakim and A Tribe Called Quest, he certainly succeeded: 1993 hits on all the pleasure centers from the golden age of hip-hop. But that’s not what he intended. “I made 1993 to speak for and to people in their twenties everywhere,” he says. “People need that confirmation that someone else is in these shoes too.”

So, with millennial subject matter and a ’90s aesthetic—soulful samples, boom-bap drums—songs like “For Sallie Mae” and “August 28” speak to the reality of being young, broke, and ambitious in the Bay Area, a reality Caleborate knows all too well since moving here five years ago.

Born in 1993, the kid known as Caleb Parker grew up in South Side Sacramento. At age 10, he immersed himself in Kanye West’s The College Dropout, particularly the song “Last Call,” which inspired him to pick up the alto sax. (“Allure,” from Jay-Z’s The Black Album, was another song on heavy rotation.)

He eventually went to Sheldon High, where he played basketball, did some theater, and started writing music in junior year—an anomaly in a mostly white school, where students often referred to him as “that black kid that raps” (he still uses “TBKTR” as his publishing acronym). In 2011, his dad went through a divorce, moved to Atlanta, and suddenly left his son to live with his brother in Berkeley: “One bag, no money, and a couch where I lay,” as he raps on 1993’s “August 28.”

There are passing mentions on 1993 of Caleborate’s dad’s time in jail, and when I ask about it, his normally upbeat demeanor turns pensive. “I don’t think it was mentally healthy for my dad to leave California and go to Atlanta,” he says, softly. “When you’re mid-50s and you’re away from your kids, your grandchild was born and you’re not there for that, your brother passes and you’re not there for that—you’re not there for any of these things, and you’re alone? Me and my dad kinda share the same mind, so I know how potentially dangerous being alone and having that kind of idle time can be.”

Disorderly conduct was the charge against his dad; it involved getting upset with some kids in the neighborhood who were doing something they shouldn’t have, but that’s all Caleborate can really say. He didn’t even know where his dad had disappeared to, until he and his family turned to Google and found his dad’s name in the county jail records. It was a shock to the son who spent every single day with his dad until age 18, talking about everything, receiving guidance.

“I worry and I’m concerned for his safety,” says Caleborate, who now stays with his aunt in Berkeley. “But then at a certain point, I just washed my hands of the situation. And I think that’s the scariest part of all. I love my dad and I miss him, but I’m worried that maybe I’m OK now, you know what I mean? That’s what scares me. That I could say, ‘I’ll take it from here.’”

His dad was in jail for over a year. Caleborate kept busy writing and recording an album, Hella Good. He didn’t tell his dad about it.

Hella Good was promoted in a distinctly 21st-century fashion: through rampant, repeated commenting on YouTube videos by artists to whom Caleborate’s own music owes a debt, like Chance the Rapper, Childish Gambino and J. Cole. His pitch was simple.

1.I’m a 20 year old rapper, student and graphic designer
2.I’m going to an Art University studying to be news broadcaster, but music is my main dream.
3.I work on campus at my school as well as off campus assisting and eat ramen for dinner, I really work hard AND chase my dream at the same time!
4.I have two albums out now and I’m working on another album all on my own dollar!
5.I REALLY hate spamming, but it’s all I got. Give me a (“THUMBS UP”) so others can notice me. THANK YOU! 🙂

The tactic worked. (Most of the replies took the form of “I wanted to hate you for spamming, but can’t lie, your shit is tight.”) He made enough of a splash to attract fellow East Bay hip-hop talents like G-Eazy, who last year appeared on the single “Want it All” free of charge; to go on a west coast tour with P-Lo and Kehlani’s DJ Noodles; and to take a hiatus from attending Ex’pression College to focus on his next album.

The Friday before 1993’s release, Caleborate performed in Lower Sproul Plaza at UC Berkeley to over 1,000 people, warming the stage for headliner Kehlani. Though technical issues interrupted the set, he showed skilled ease on the mic (he staunchly refuses to rap over his own vocals), and covered for the set’s glitches with his natural charm, shouting out popular spots on Telegraph between songs.

Likewise, 1993 is more polished than Hella Good, and more focused on every level. Its production, by P-Lo, Julia Lewis, Mikos Da Gawd, Wax Roof, Ian McKee, HBK’s Kuya Beats, Cal-A and more, is a smooth, satisfying IV drip of memorable beats and samples. And Caleborate’s lyrics, in particular, operate like a Jenga puzzle, with key words and phrases holding up entire lines later in the song.

And though his natural nasal tone is initially reminiscent of Chance or Kendrick, he’s grown into a voice and flow that’s indisputably his own, used to amplify issues like gentrification and displacement—issues that have decimated the black population in the Bay Area (and have priced out fellow rap artists like Zion-I).

But like Lil B, the most positive rapper in the Bay Area and perhaps the world, Caleborate crafts songs that always reach for a sense of hope. There’s a conspicuous lack of violence in 1993, for example, even though just this year Caleborate lost a childhood friend, Darien McLaurin, who was shot, Caleborate says, “over some gang shit in Sacramento.” On the day we walk around Berkeley, he and Kale, his DJ, repeatedly wrestle with the tragic and untimely death of Terrance McCrary, Jr.—a.k.a. T-Mack, the 22-year-old Berkeley High grad who was shot and killed last month.

That may explain Caleborate’s subtle reference to certain white rap fans in 1993’s “250 AM”:

The hipsters all at the shows with the money and the clothes
and they all wanna say the N-word
Oooooh, the truth hurts, don’t it?
My friends die over shit you flauntin’

“I did a show with Vince Staples for Noise Pop, and I had this weird moment where I’m watching him perform ‘Blue Suede,’ and I’m lookin’ in the crowd, and it’s like… not very many black people,” Caleborate says. “Everyone there, they all fit this hipster demographic: they kinda look like techies, they got thick mustaches and flannels, and you’re listening to these lines from ‘Blue Suede,’ and you’re like… does this even make sense? I don’t want you to be down because it looks cool and sounds cool. I want you to be down because you actually understand what it’s like in my shoes, or at least want to understand it. Not just to wanna take the picture, or be in the crowd and say that you were doin’ some hood shit when my song came on, and then you go back to your regular life and that’s it.”

The UC Berkeley campanile cuts off Caleborate, loudly tolling its bells across campus, which gives him a moment to think. He looks up. “Just know that it’s real for us,” he says. “It’s not just a lyric in a song. It’s a moment that I have to live with for the rest of my life.”

Hiero Day is a joyful celebration of Oakland’s heart and soul, an annual block party that brings together younger artists like Rexx Life Raj, Elujay and Rocky Rivera with the old guard standbys of Souls of Mischief, Too Short, Paris and more. At this year’s fest, Caleborate has an early afternoon slot on a sunny side stage, but it doesn’t keep the crowd from losing their mind.

It’s a party setting. Caleborate sings “Consequences” (“I just wanna chill, smoke, drink an’ be cool”), points to his shoes when someone yells “Free the Ankle!” (wearing no socks has become his hashtag trademark), and, for the song “Saggin Par,” jumps off the stage and breaks through the metal barricades separating him from his crowd. The beat drops and bedlam ensues; a pit forms, Caleborate screams along with dozens of others in body-slamming cathartic release, and for a moment it actually feels like a punk show from the year 1993.

Then, back on stage is Caleborate, the skinny bald kid who looks on the bright side. The kid who’s seen his dad go to jail, his friends killed, his peers suffocated under a mountain of debt, his city mutated by crippling changes, his culture co-opted by techies, and he starts talking about the one thing that keeps him afloat: having a dream.

“I appreciate y’all because y’all came out,” he says, wiping the sweat away. “We all blessed because we alive today, OK?”

Caleborate’s new album ‘1993’ is out now. For more, hit him up on Instagram, or walk down Telegraph with no socks—you’ll run into him sooner or later.