A Night With FunkFlex, New York Rap Historian and Booster

“Where you find the energy to be on this type of time?”

Fat Joe had been awake since 5 a.m. to prepare for a CNN segment, and now it was almost 10 p.m., and he was fading. But FunkFlex, the New York radio mainstay, had requested his presence at a small gathering of the New York rap tribes a couple of nights before Thanksgiving, and so Joe was holding on just as Flex was revving up.

For more than three decades, Flex has been the carnival barker-in-chief of New York rap, a nighttime radio fixture on Hot 97 (WQHT-FM) — the rare D.J. whose hysteric chatter can merit real-time listening — and a stalwart of nightclubs throughout the city and the tristate area. He is a humorist and an antagonist, sometimes with a target in mind, and sometimes simply for the theater.

In the main, he is a booster, a barometer for how New York understands itself through its hip-hop — a bridge from the 1980s to the present day. In the era when New York rap was at the center of hip-hop globally, Flex (then Funkmaster Flex) was at the center of New York rap. But those are bygone days now; even with the rise of drill, New York rap remains a regional concern. And so lately, Flex, 55, has been wondering how he might bring New York back — if not to the center of the conversation, then at least to a sense of hometown pride.

Last week, he put out a call to see what might happen if various generations all ended up in the same room, the studio on West 25th Street where he usually films his freestyle series for YouTube. He put the call out to some of the city’s young rising drill stars, and also into the group chat he has with some of the city’s elders: N.O.R.E., Busta Rhymes, the Lox, Fabolous, Fat Joe and more.

From the beginning of the night, dividends were being paid. B-Lovee, one of the most promising drill rappers from the Bronx, was telling Fat Joe, three decades older, about his neighborhood. “That’s the first place I ever seen KRS-One in person,” Joe told him. “Van Cortlandt Park, South Bronx, block party.” Sheek Louch, one-third of the Yonkers rap crew the Lox, looked on. Flex turned to B-Lovee and said he couldn’t tell him who had been supplying him with his music that hadn’t yet come out, but that it was in good hands.

For the last few months, Flex has been setting aside time on his Thursday night show to play unreleased music, a means of pushing back against the algorithmization of hip-hop. Local radio D.J.s were tastemakers once, but playlists are far more powerful now. Flex knew this, because he himself had fallen victim to them.

“I was going the easy route — Apple, Spotify Rap Caviar. I was picking my music through there for a while,” he told Jim Jones later that night. “I called you one morning like 7 a.m. It’s Thursday, things are being released and my phone ain’t ringing. Nobody’s asking me to play [expletive]. It bothered me — I ain’t hot? What I feel don’t [expletive] matter?”

Flex had to accept that he’d lost a little bit of his gusto over the years. And so he recalibrated, digging in and seeking out music no one had heard — songs that hadn’t yet hit streaming services (even if just a few hours in advance of their official release), or more excitingly, old unreleased songs languishing on hard drives. “I’m getting a lot of songs that had samples that didn’t clear,” Flex said. “I’m getting a song that didn’t make ‘Paid in Full,’” the classic 1987 album by Eric B. & Rakim.

As he was saying this, there was a light commotion at the door as Roddy Ricch, in town from Los Angeles to promote his “Feed tha Streets III” album and the only non-New York rapper in attendance, came by to record his freestyle for Flex’s YouTube series. When all three members of the Lox — Jadakiss, Styles P, Sheek — entered the studio after he laid down his verse, he melted just a bit: “They done put the pressure on,” Ricch said. “Real spitters in the building.”

After Ricch left, the hot seats went to Jim Jones, in a lavender Moncler puffer jacket and a tangle of chains, topped off with one featuring a diamond portrait of the Mexican drug kingpin El Chapo, and Dyce Payso, one of Jones’s protégés. After Dyce Payso rapped a verse, Jones caught a feeling and murmured his way through some untested lines. “Everyone came up here with bars,” he said sheepishly. “I’m just breathing.”

Flex and Jones got to talking about the golden era of the Diplomats, when Flex was perhaps a tad late in playing their music on the radio. Cam’ron, the crew’s leader, brought him to West 140th and Lenox Avenue to see the potency of the movement firsthand. “Did I catch up fast?” Flex asked Jones. “Very fast,” Jones concurred.

Now, New York was starting to feel familiar to Jones again. “Shout out to all my drillers out there,” Jones said. “It’s feeling like ’02 when I step outside. It’s feeling like the Tunnel.”

To Flex, Jones added, “You got the city looking forward to Thursday again.”

Following the success of his Thursday night anti-algorithm sessions, this gathering was the first step Flex was planning toward providing New York with a sturdier foundation. He described a plan to put out an old-fashioned mixtape — physical copies only — featuring unreleased songs and freestyles that aren’t otherwise available on the internet or streaming services.

Just after midnight, he was discussing his upcoming club schedule while picking at a Tupperware container filled with cucumber and cherry tomatoes. “Every three months, we gonna do a clubhouse session like this,” he said to Tat Wza, his longtime consigliere, who had been manning the boards all night.

B-Lovee had been there all night, mostly quiet, mostly listening. When he finally got up to leave, Flex told him to pull up to the New York-centric Thanksgiving party he was hosting, featuring local royalty French Montana and Lil’ Kim, and also the drill stars Fivio Foreign and Ice Spice. “We gonna set a tone,” he assured him.