It’s a low-key winter afternoon and Milo — the 26-year-old rapper, producer, and Ruby Yacht label owner who appears at Drom on February 13 — is holed up inside the Soulfolks record store in Biddeford, Maine, that he plans to open in April. He’s recalling the times when he’s had to kick people out of shows and college Q&A sessions for hurling racial insults. “Guys would come to my shows, walk to the front of the stage, and say, ‘Milo, you’re a nigger,’ ” he says. “White guys. At the show. What am I supposed to do?”
Milo classifies these incidents as part of “a time-honored American tradition of being able to pay money to come and throw expletives and physical violence at black people.” They’ve mandated he develop the ability to flip into “someone who speaks violence” and play the role of an “enforcer” as he travels the country performing music. “To do that over the course of years and get good at it is not something that I’m defined by,” he says. “But that’s a vocabulary we can talk about, too.”
The vocabulary that usually defines Milo — who also releases projects under the Scallops Hotel guise — is more intellectual than visceral. He’s been anointed one of the leading lights in an art-rap scene that has roots going back to Los Angeles’s Project Blowed stable in the 1990s, was kept simmering by the Hellfyre Club label during the 2000s (which he recorded for), and now counts Open Mike Eagle as its chief torchbearer.
Milo’s sound is typified by woozy and relaxed production embellished with off-kilter atmospheric ticks. Over this he lays down lyrics quick to reference literary, art, and philosophical figures, including painter Jean Dubuffet (discovered by Open Mike Eagle during a museum visit with Milo) and French New Wave director Agnès Varda. Book-smart boasts like “I be to rap what Keynes be to Locke” and “I feel like Arthur Miller when The Crucible drop” don’t exactly scan as righteous fight club music. But a defiant nonconformist spirit bubbles through Milo’s work, fired by an upbringing completely soundtracked by hip-hop.
Milo dates the dawn of “being conscious that this is hip-hop” to age four, when he put a cassette of Coolio’s “Fantastic Voyage” into his mom’s purple boombox. His mom’s taste, though, skewed more toward the socially conscientious side, and he credits her with first playing him the Afrocentric styles of X Clan (whom he referenced on 2016’s Too Much of Life Is Mood) and the firebrand rhetoric of Dead Prez. “My mom and I would be in the car talking about, ‘I’m down for running up on them crackers in their city hall!’ ” he says. Factor in a father who was all about Biggie, plus an uncle-turned-babysitter who was an MC in Chicago, and Milo received the sort of well-grounded foundation that’s allowed him to channel his hip-hop forefathers while presenting his own spin on the culture. The heart of his music taps into what was once hip-hop’s cardinal rule: Be original.
Against this background, it’s natural that Milo rallies against the sense of a growing conformity across music and society — even if it’s meant that he’s started to be pigeonholed himself. “I prefer people who chose to occupy the fringes and who chose to be avant-garde with their shit because they know the connection art has with reality,” he explains. “It’s fuckin’ easy to be part of the Get Along Gang and do what [record labels] expect of you, and when they expect so little of you it makes you look like a fuckin’ dummy.
“As conformity devours us as a country, it’s really important that artists choose to be weird, and it’s a serious undertaking. I want to be loquacious, I want to talk too much, I want to have clarity and not have clarity at all. I just want to fuckin’ poke at it all the time. As artists we have a duty to our communities and our society to say some shit that not everyone else can say.”
And if that results in some listeners assuming your music needs consuming with a Wikipedia page permanently onscreen to decode some of the lyrical references? “Well, damn, that’s a pretty thin definition of what I do,” Milo says with a hint of bemusement. “If somebody thinks that, that’s cool — I’ma keep it funky though.”