Milano Constantine "Closer"
Paragraphs of a poet's soul.
Manhattan-bred MC Milano Constantine formally came in the game back in 2000 as a newcomer on the self-titled D.I.T.C. crew album. It’s not easy to stand out amongst heavyweight MCs like Big L, Big Pun, Fat Joe, Lord Finesse, Diamond D, A.G., and O.C., but Milano held his own, ripping verses on “Where Ya At” and a personal favorite of mine, “Hey Luv.” Here’s the story of how he met D.I.T.C. producer Showbiz and ended up in the mix, courtesy of his interview with Unkut back in 2013:
Milano Constantine: That was a mutual friend, through my moms. It was like, “That’s Showbiz! Oh, shit! ‘Soul Clap,’ that’s wild!” I ain’t wanna run up on him and tell him I could I rhyme. I finally did, and I blew his mind. He was like, “Yo, you sound like Nas or somebody.” I think I was like twelve or thirteen. It’s wild, I’ve known Show for a long time.
When I got outta high school, that’s when I really set forth. Showbiz was like, “Come to D&D, we’re gonna do a cipher.” When I got there, it was Big Pun and fifteen other dudes. I think Sunkist was there, O.C. I set it off, I look at Pun and I’m all nervous, jittery and shit, and I just went for mines, like the old Diamond D joint. I just started going off, then he went, I went, the other guys went and me and lo and behold, me and him was the last people in the cipher. He spit some artillery shit, and I just bow-out gracefully and start laughing, and he start laughing with me.
At the end of the session he said, “Yo, I love your shit. I would like to do a song with you.” I’m like, “You would like to do a song with me? How the fuck is that possible?” That’s how we did “Where You At.” I met him on a Wednesday and went to the studio on Friday. It was amazing, I couldn’t believe it.
Milano landed a deal with Warner Bros., but his album The Believers never saw the light of day (even though it had production by monsters like Buckwild, Showbiz, Lord Finesse, and T-Ray) until about six years ago when it was given a proper physical release via Slice Of Spice. It’s currently unavailable on DSPs, but check out this super-dope track off it, “Awful,” which is actually not produced by any of the names listed above—it’s credited to D.I.T.C. affiliate Ahmed.
Milano Constantine “Awful”
Milano’s been pretty prolific through the past decade (even through battling health issues), dropping projects with Showbiz, DJ Skizz and Marco Polo, Big Ghost Ltd, DJ Ready Cee, and more. Lyrically, he’s always crazy nice with the rhymes. The clever wordplay, the swift flow, the fly talk—I’d throw him right up there at or near the top of my “Most Underrated MCS” list any day. Listen to him rip this.
But beyond his penmanship, his production is ill, too. In fact, one of my favorite songs of his, “Closer,” is self-produced. It’s off a two-song single he released back in 2016 titled P.O.P.S. (Paragraphs Of a Poet’s Soul), dedicated to his late father.
Milano raps, “I’m twistin’ lime, had drinks on the rocks/Go off in deep thought when I think of my pops/I’m at the brink when I stop, almost, seen the goal post/Listen to these jewels that I got from these old folks/’93 Volvo, on these tracks pole vault/Hot over the stove I’m in my own zone/Rowed the boat up shit’s creek, it’s knee deep/Plus my family got the thing-thing if need be/Paint the scenery up-close and vivid/Off drumrolls my vision is cutthroat, you dig it/Pour rum out for spirits, libation/Rock crowds Live Nation I lace them/I’m getting closer…” Sheesh.
IP’S PICK OF THE DAY 9/9/25: Milano Constantine “Closer”
He laced Queens MC Aye Wun on this “Clyde” cut too.
At the end of the day, it’s guys like Milano that make me still love rap music. MCs who care about their craft and get busy regardless of the accolades. Sometimes I just skip the songs and watch this on-air Shade 45 freestyle with Tony Touch and laugh at how good he is.
Nuff respect to the great Milano Constantine. Gotta celebrate the unsung heroes of this shit, because if we don’t, who will?