Long Island may not always get its flowers in Hip-Hop, but from Public Enemy and EPMD to Rakim and De La Soul, the 516 is sacred ground. Enter Jaeo Draftpick. He’s repping Long Island with pride, lyrical grit and a new hustle.
DJ Thoro sits down with the MC-turned-entrepreneur, whose journey includes high school field trips to Violator Records and overcoming legal setbacks. Fresh from a London trip, he’s got a new single “Twisted,” a tribute to the Keith Sweat classic. He’s got stories, punchlines and a chip on his shoulder for every time Long Island is left out of the Hip-Hop conversation. Read on for the most entertaining, raw and unapologetic version of Jaeo yet.
AllHipHop: You kicked this off with a slick line—”The kid from the island like Gilligan.” Where exactly are you from?
Jaeo Draftpick: Long Island all day—everywhere from Westbury to Hempstead. I don’t claim just one area because Long Island is huge. I rep the whole thing.
AllHipHop: Let’s play a little Hip-Hop trivia. Name some icons from Long Island.
Jaeo: Oh, easy. Rakim, Biz Markie, Keith Murray, Prodigy, Granddaddy IU—RIP. Even Meth lived out there. And Roc Marciano. People forget about these legends.
AllHipHop: You’re up here promoting something. What’s the latest?
Jaeo: I just dropped a new joint called Twisted 2K25. It channels the Keith Sweat classic—nah, not sampled, but inspired by it. Produced by Dub Easy. It’s smooth, it’s fire, and it hit streaming March 21st.
AllHipHop: You mentioned performing it for the first time in London. How’d that happen?
Jaeo: Crazy story. I planned a work-play trip to London with the homies. Someone’s relative owned a lounge. I played my music there, they rocked with it immediately. Invited me to perform the next night. Whole thing was organic. That vibe was love.
AllHipHop: You talk like a student of the game. What set it off for you?
Jaeo: A field trip to Violator Records in high school. Shout out Mr. Jenkins. I met Chris Lighty—didn’t even realize how major he was ‘til later. But that day made me want to be in the business—somehow, some way.
AllHipHop: That same Mr. Jenkins later banned your video shoot?
Jaeo: [laughs] Yeah, same dude. We shot a video in a school he was principal at later. “Look At My Drip.” Choir was in it, lyrics weren’t wild—but they asked to take it down. Same guy who helped spark the dream tried to shut it down. Wild.
AllHipHop: You also mentioned past struggles. Can you talk about some obstacles?
Jaeo: I’ve been in and out the system. Violations, 30 days here, 45 there. Having a kid in high school. A lot of things pulled me away, but I kept coming back to music. And it paid off—“51631” landed me a deal with Tommy Boy.
AllHipHop: That’s major. And you didn’t stop there. You launching a dispensary now?
Jaeo: Yup. It’s called Lifted Essentials in Wading River, Suffolk County. One of those conditional licenses came through based on prior convictions. Crazy how those Ls turn into Ws. That’s why I don’t glorify the rap sheet—but I own it.
AllHipHop: You dropped a freestyle earlier. You still a spitter first?
Jaeo: Always. I do the songs, the commercial records, but I came up writing to Nas on karaoke machines. I rap for real. That track got me noticed.
AllHipHop: If you could collab with anyone—dead or alive—who would it be?
Jaeo: Cam’Ron is one of my favorite rappers. A-Boogie too. Old Kanye—not KKK Kanye. Michael Jackson, no question. I used to dress like him as a kid. That’s real influence.
AllHipHop: What separates you from the 30,000 other rappers out?
Jaeo: I’m versatile. I can do trap, boom bap, melodic stuff. I’m from Long Island, forgotten in Hip-Hop. I rap, but I also build. Music got me into business, ownership, expansion. You ain’t got to sell your soul for success. Just grind.
AllHipHop: And the last project?
Jaeo: Nice Try Wrong Guy. That was the last album. The next one’s Just a Guy. Stay tuned for that. Everything I do is intentional.
AllHipHop: What does “Jaeo” stand for?
Jaeo: Just About Everything Outstanding.