Tucked away on the ninth track of what I think can truthfully be called one of Milo’s darkest, most prickly releases — Plain Speaking — Milo says

I imagine myself saying on the Oprah Winfrey Show That life is hopeless and finicky It’s morbid and limiting to be constantly absorbing their energy Translating context This is a pamphlet explaining the uselessness of the rap song’s conquest Your measurements seem prophetic I interjected They mistook my rhetoric for poetics

My basic thesis for the rest of this piece is going to be that this line has a lot to say about the way Milo thinks about things like art’s engagement with the world, what kind of art he’s making, and how that art’s been perceived.

To be straightforward: I would say that — yes — Milo has made music with a lot of references in it and — yes — Milo is more ‘artsy’ than most rappers working today — — but if you appreciate his work as if these two things were its most important characteristics; if you understand Milo’s corpus as something which was made in and belongs to an ivory tower; if you treat his music as if its only proper place was in that finest of lumber rooms, among the unicorn horns and broken pots; I would say that Milo would be very sad indeed.

He would be very sad — and angry, even, which is an emotion a lot of people seem to (sub)consciously ignore in Milo’s music.

Timpko, for instance, references Milo’s time in California working with the Hellfyre Club, a west coast collective headed up by Nocando and peopled by such illustrious names as Busdriver and Open Mike Eagle. Although Timpko makes the (quite correct) point that Milo was at first overjoyed to be working with this group, and that he undoubtedly grew a great deal as an artist while he was a member, his account of Milo’s departure is a little bit sunnier than I remember it. I remember a lot of twitter exchanges about work not being compensated; Milo in recent interviews has spoken about the economics of LA not working out, about things as concrete as rent prices and things as pervasive and abstract as class interests affecting the art made out there.

Indeed, Milo’s time in LA, and the events surrounding his departure, seem to have made him much more cynical — or at least guarded — in his approach to art. Plain Speaking is, after all, work from the period immediately after Milo relocated to the midwest, and it’s basically anti-rap. The semi-spoken-word style Milo’s received much praise for is the primary method of delivery; aside from lines like the one quoted above — “This is a pamphlet explaining the uselessness of the rap song’s conquest” — there’s other chilly meditations, like “I love rappers how shepherds love sheep for whool,” which is the outro for ‘Bookoo Bread Co.’, and “Your favoriate rapper talks too much about his fucking self,” which is the twice-repeated intro to ‘True Nen.’

The more general point is that Milo has matured, a lot, before all of our eyes, and he knows it, and he’s been telling us as much in his own beautiful indirect way for a few years now. The more specific point is that Milo seems to have grown more angry than sad, over his past few releases, and this is something a lot of the discussion about his music seems to miss.

This anger isn’t just about certain aspects of hip hop in America right now; it’s also manifested in a growing political consciousness in Milo’s work. Stfdc, for instance, contains what might become one of his most beautiful and undying koans — “The black man’s Bruce Banner is an iCamera” — as well as more than a few lines about the racial tensions in America, the blithe hypocrisy of some of Milo’s white fans, and more. Milo is increasingly looking out at and speaking of the world, in other words; his songs aren’t just about what’s going on in his own head. This isn’t to say that he hasn’t thought about these things for a while, and it’s not as if his earlier records are completely apolitical, either — but the point anyway is that politics is a part of his work which is growing in its pronouncement.

At the same time, he’s distancing himself from the wunderkind aesthetic which people first started loving him for. He has a line in the opening track of stfdc that skewers the kind of overly-cerebral wordplay I think (and I think Milo thinks) a lot of people still associate with him: “You scrawled the word ‘discursive’ in / cursive / and called yourself subversive / we all belly-laughed” (emphasis my own but you can hear it in the song.) Then there’s the more overt statement from ‘Going No Place’:

That’s not boasting You were used to me rapping my book list Indeed a nigga might look bookish You can be next in line to catch a hooked fist But nah, right?

To reference an old Milo standby: I’m reminded of the way that David Foster Wallace took pains to distance himself from his earlier work, after he had written Infinite Jest. D.T. Max, Wallace’s biographer, recounts how at book signings, when a longtime fan would bring A Broom of The System, Wallace’s first novel, for him to sign, he would make an exaggerated little show of grimacing knowingly and signing That Old Thing.

And I can’t help but imagine Milo reacting the same way to copies of Things That Happen at Day / Things That Happen at Night, or A Toothpaste Suburb — a laugh, a self-conscious scratch of the head; signing Those Old Things with the same knowingness Wallace did. The knowingness of an artist who can visualize, almost, the distance they’ve walked since they first made those intimate signposts of what was going on in their heads.