ASAP Rocky Names His Top 10 Flyest New York Rappers of All Time

Pretty Flacko has shown some love to the Big Apple's freshest dressed MCs, but do you agree with his list?

July 17, 2026

ASAP Rocky has long been considered one of hip-hop's flyest rappers, and now he's sharing who else deserves that title, specifically from his home of New York City.

Sitting down with Complex's Izzy Izzo at the re-release event for the 1994 classic Puma Suede, Rocky was asked to name the five flyest New York rappers of all time.

As he began naming people, Rocky decided to double the answers. "I got 10 for you," he said, before going on to build a list that covered four decades of NYC style.

Rocky began by setting one ground rule: he would be excluding himself in order to "save room" for others. He then ran his 10 picks (although, he actually named 11) in a loosely ranked order.

Rocky put Fabolous near the top without hesitation, a pick that drew no pushback from anyone in the room. Cam'ron came next, but Rocky widened the frame immediately: "Well, Dipset, we got to say Dipset," he said, taking the whole collective.

Grand Puba and Slick Rick made the cut, as did Mos Def (aka Yasiin Bey), who he called "Pretty Flacko Sr." and described him as "one of the flyest mothafuckas."

West Coast legend 2Pac got a mention, with Rocky pointing to the late legend's Harlem roots and a series of fashion-world firsts. "He was born in Harlem," he said. "First to wear Versace. First to the Armani show, front row."

He then floated Bad Boy as a collective, specifically Mase, Diddy, and 112, saying: "Puff had everybody looking like fly." Nas got in after Izzy brought up the Queesbridge legend. "We gotta go Esco," Rocky said.

The DMX and Ruff Ryders slot came with a specific sartorial memory, as did his next pick, Wu-Tang Clan. "DMX was fly, and I loved how the Wu-Tang was dressing, bro," Rocky said. "For me, I loved the way ODB was dressing, OD baggy dungarees with a flannel hoodie."

For what ended up being his 11th and pick, Rocky kept it close to home, showing love to ASAP Mob. "And number 10, I'm going to just throw ASAP Mob in there," he said. "We was going crazy. Y'all know we went crazy. You know what I'm saying? Keep it a buck."

Check out ASAP Rocky's full list below: