Pitchfork writer Alphonse Pierre’s rap column covers songs, mixtapes, albums, Instagram freestyles, memes, weird tweets, fashion trends—and anything else that catches his attention.

Baby Osama is New York as fuck. On a curb, in the Lower East Side, she brags about how there is nobody in the city messing with her Nike ACG boot collection. In Bed-Stuy, she turns a routine interview into a new Come Up DVD. And, over the Williamsburg Bridge, she’s relaxing in the back of a Suburban with cracks in the front window as her 16-year-old little sister holds down the aux cord with a mix of Max B deep cuts and five-borough favorites. At one point, while Method Man and Redman’s “How High” blasts out into the bustling Saturday afternoon city streets, Osama, born eight years after Meth & Red’s 1995 song dropped, leans over to her sister and says, “We have to ask Daddy if he remembers this one.”

The goal for today is to make it to Osama’s set at the fourth edition of Young World, a multi-generational, free music festival started by New York rap luminary MIKE. Held at Herbert Von King Park, in Bed-Stuy, the day has fast become a signature summertime event for the local hip-hop community. Baby Osama, out of the South Bronx, is included on the lineup beside names like lyrical giant Earl Sweatshirt, sing-songy viral Brit Skaiwater, and beat-making legend Pete Rock. It’ll be the first time she ever rock outs in front of a crowd this massive.

Getting there proves to be the hardest part. Our driver for the day is a Jersey City man named Flip, who is joining in on the party a little bit too hard. The throwback New York playlist in the car has him feeling himself, freestyling any chance he gets. (He’s not bad; he could have at least held down the JR Writer spot in the Diplomats.) When he stops the car so Osama can grab some cheap eats at an LES empanada hotspot, Flip, a self-proclaimed Max B superfan who likes to call himself Flippavelli, interrogates Osama for her NYC rap knowledge.

He brings up French Montana. She brings up Chinx. He brings up Stack Bundles. She’s unfamiliar, but instantly curious, suspending a hunt for a lighter to google the late Far Rockaway rapper. Meanwhile, Flip is in disbelief: “You’ve never heard of Stack? He was the gorgeous gangster. The handsome hustler. The heartthrob of the hood.” As soon as we’re back in the whip, Flip throws Stack’s “That’s Me” on at max volume, and Osama and her small group of fashionable friends nod along in the back. When the song ends she requests more Stacks.

Osama’s New York hip-hop enthusiasm is no surprise. Her best song of the year is “Free Max B,” and it’s built on producers Saint and Divine’s flip of Max’s “Porno Muzik,” turning the soulful lusting of the original into a bouncy, “sexy drill” anthem. On the song, a featherlight Osama sounds like she’s singing underwater, and her lyrics are a mix of romance and raunch. The best thing about her music is that, despite being part of a new wave in the city, her flavor bridges the gap between New York old and new. Even her stories of relationships and running around the city with her friends feel like they could have happened in any era. That’s true, too, of her new mixtape, Sexc Summer, a short collection of midnight club songs with heart. She’s jealous on “If I See U Wit Her”; horny on “Body”; heartbroken on “Did Me Wrong.”

The mixtape is the latest addition to Osama’s burgeoning, versatile catalog. My introduction to her was the pluggnb-ish “RX Baby,” a melancholic Auto-Tune-aided ballad. But she’ll pretty much sing-rap over anything. Jerk? Sure, and with a sentimental bent. Jumping in on the New York club drill wave? You bet. Most of the time, it’s simply swagged-out, spacey croons and lilts, like personal favorites “Pacer Test” and “Feelin Like Sexy Red.” Nobody on the Young World lineup sounds exactly like her. “That’s the best part, I don’t fit in,” she says, adjusting the sling on her arm that she got a few days ago after getting into a scrum outside of the airport. Shrugging everytime she tells the story.

The first obstacle on the way to Young World, though, is another performance at a thrift store event near Union Square. Inside the shop, there are teenagers (and, inexplicably, a few toddlers) digging through enormous piles of clothing just plopped on the ground. About half a dozen influencers from the fashion corner of TikTok are there, too. For her very casual concert, Osama is handed a mic, and a circle forms around her as she does a 15-minute set in the middle of the floor. The audio is a little muffled, but she feeds off the energy of her friends and sister who are grooving right in front of her with their arms locked. The toddler to my left hits a dance move to “Free Max B.”

After the set, it’s off to Young World. Flip is driving like a madman, and Osama and crew keep requesting Ja Rule’s “New York,” but he keeps playing tracks from a random DJ Clue mixtape. His car is malfunctioning a bit, too, adding to the chaos: The windows are opening and closing, and the air conditioner keeps turning to heat. By the time we get to Herbert Von King, Osama has only 10 minutes until she’s supposed to hit the stage. But she’s not concerned, making herself a drink and getting her hair combed by her sister, as her manager rings again and again.

Osama is on after MIKE, who is finishing up his performance, the crowd in the palm of his hands. She doesn’t seem to have much jitters or any need for a pre-stage ritual. Next thing we know, Osama and friends are on the stage, staring out into the sea of festival-goers. At first, Osama is tamer than I expected, and it’s clear that she’s going to have to win over the crowd, many of whom are probably here for Earl. She yells at them to move, and her friends show them the “Reemski.” As she gets the hang of it, she starts to jump around and her energy starts to translate into some moshing. For her last song, “I Don’t Mean It,” which puts a thudding twist on Beanie Sigel’s “Feel It in the Air,” she sips on her drink and stands on top of a massive speaker, swinging her hair around. In that moment, she feels incredibly cool, the most important thing a New York rapper can be.

Mixtape of the Week: Bloody!’s The Players Club

It’s nothing new for a rap mixtape to be all about sex and drugs, but Bloody! makes his music as raw and degenerate as Spring Breakers. His new mixtape, The Players Club, is extremely grimy, and, while the lush beats try to suggest that this is a project of love and not debauchery, it is all debauchery. He’s also such a blunt and vulgar rapper, and his melodies are so imperfect and naked, that songs like “Drug Love” and “Azarath” feel like they take place on that dingy mattress on the floor in Carti’s “Ketamine” video. Maybe it’s in poor taste to play the tape as much as I have already, but I’m not above some summertime depravity.

Lil Bo 954: “Fancy”

Lil Bo 954 and funky Detroit-meets-South Florida beats go together like Tom Thibodeau and Villanova guards. The harder the bassline and the thump of the drums, the better. “Fancy,” the finale on Lil Bo’s new tape One Step Away, is exactly that. The smooth, sped-up vocal sample bleeds into a rhythm that rattles like an old lawnmower, which is perfect for Bo’s laid-back (but never inaudible) flow. He’s usually good for a bar or two that I’ll remember—this time it’s “You the type of nigga that don’t get no money, just post pictures”—but he’s best at catching a groove. This is the kind of easy-listening Florida rap that just makes you want to hit cruise.

SuperThrowed Fay Fay: “Simon Says” [ft. Ghost53206]

There’s a new SuperThrowed Fay Fay mixtape—out on YouTube only, naturally—called Baby Driver. It makes sense because all of the Milwaukee rapper’s songs sound like him and his guys are reading off their phones while swerving in highway traffic. He always seems to be in a rush, like the recording booth will automatically lock and fill with hot lava if he takes more than two minutes to lay down his drug-dealing flashbacks. If you called this music half-assed I wouldn’t disagree, but it’s that no-fucks sprint that gives songs like “Simon Says” the feel of a flashy montage. Based on their bars, Fay Fay and frequent sparrer Ghost53206’s movie would feature scenes from the interrogation room and the kitchen, plus close-ups on their new watches and buffs. Producer TaeHuncho’s lush, gleaming bent on high-speed Milwaukee slap music makes the fast life feel a little dreamy, too.

A Meetup Between Rap Column Favorites Xaviersobased and Earl Sweatshirt

Now that I think of it, Xavier would sound pretty good on “East.”