It’s such an oddly specific and low-stakes flex: “I’ve been on every podcast that I listen to.” It’s also, presumably, an entirely true statement. If you’ve ever heard Open Mike Eagle on a podcast, you already know that he’s an ideal podcast guest: funny, gregarious, open-hearted, interested, informed enough to speak with some credibility on whatever the topic might be (especially if the topic is professional wrestling, which it frequently is), blessed with a warm and sonorous speaking voice. He should be proud at being on all these podcasts, at becoming the soundtrack to all these people’s dog-walks and dishwashing marathons. But nobody, with the possible exception of Joe Rogan, is getting rich off of podcasts. And Joe Rogan already had Fear Factor money.

Open Mike Eagle is a rapper who likes to make big, towering statements. Last year, that meant the release of the album Brick Body Kids Still Daydream, a full-length exploration of the now-demolished Chicago housing projects where some of OME’s family lived while he was growing up and of the feelings surrounding those buildings. OME’s new mini-album What Happens When I Try To Relax doesn’t have any unifying concept like that, which makes it more accessible and less imposing than some past OME works. If the new record has a central idea, it’s that it takes a long and honest look at OME’s career and his place in the rap ecosystem. It also looks at decisions he’s made, like the decision to make Brick Body Kids Still Daydream: “I made a audio mural you can walk through / About my auntie that I don’t even talk to.”

What Happens When I Try To Relax opens with “Relatable (peak OME),” a song that’s specifically about OME’s attempts to be more accessible so that he can continue to pay his bills by making rap music. It’s a sort of extended inside joke of a song, but it’s also one of the more sonically welcoming songs in the man’s recent catalog. And it’s genuinely funny, too: “I don’t wear a monocle / I don’t know which sequels are truly canonical / I’m sorry, don’t follow you.”

“I’m hella political, super-political,” OME says on “Relatable,” and it sounds like irony at work. But Open Mike Eagle is political, and some of the best moments on the new record are honest and layered looks at what it’s like to be black in America today: “Through my roots, I respond, react / Cuz my folks need jobs and some Wozniaks / In my nightmares, I swear there’s some Nazi blacks / That say, ‘Pull yourself up by your Huarache straps.'” And that extends to the man’s own self-examination, getting into the layers of weirdness that come from performing for the mostly-white audiences who have always been drawn to underground rappers like him: “Hey Brain, what we doing for the night? / Tryna reach black kids in a room full of whites.”

I haven’t written at length about Open Mike Eagle before. That’s not because I don’t like his music; I do. It’s because he’s such a good writer that writing about him is an intimidating proposition. Consider this dazzling extended aside about Pearl Jam: “I think about the kids that Jeremy killed / Eddie Vedder, put something on this therapy bill / He probably made hella bedwetters / That know every word to ‘Yellow Ledbetter.'” Open Mike Eagle would probably also be just as happy if I didn’t write about him: “I’m getting bread but I’m still living in the red / If you gon’ write about me, get it airtight.” Um.

And yet What Happens When I Try To Relax is a fascinating record, one that practically demands some kind of response. It’s not as heavy or layered as some of Open Mike Eagle’s past records, but it leaves plenty to think about. Again and again, OME gets into the level of economic struggle that comes with his chosen career — the sort of career where you can be famous to people who listen to multiple podcasts but where you’re going to have to continue working, where your triumphs are going to be small and more emotional than financial. Open Mike Eagle will never be a part of rap’s A-list. He seems to be mostly OK with that: “I saw Kendrick at Leimert and didn’t say shit / I saw Vince at the club and didn’t say shit / Cuz this independent hustle is adjacent.” Those lines come from the song “Southside Eagle (93 bulls),” about which OME says, “I really wanted to write a song that was uncomfortably honest about my personal economy.” Mission accomplished.

The adjacent hustle is a real thing. For more than a decade, Open Mike Eagle’s friend and collaborator Serengeti has been making albums from the perspective of Kenny Dennis, a character who he invented. Kenny Dennis is a middle-aged Chicagoan with a thick mustache, a thicker accent, a long-past struggle with alcoholism, and a heartening devotion to his local sports franchises. Serengeti has made so many songs about Kenny Dennis. One of those songs, “Dennehy,” is a longstanding underground hit, a song that will be fun to rap along with until the end of time.

But Serengeti has been so focused on this character that he once made an album that attempted to explain why Kenny Dennis knows how to rap in the first place. (It’s There’s A Situation On The Homefront, the fictional 1993 debut from Kenny’s old rap group Tha Grimm Teachaz.) Serengeti recently announced that he’s retiring the character. It makes sense. To get this deep into one idea is to ask a lot of your audience. And when you ask a lot of an audience, it’s hard to make a living.

Open Mike Eagle is making a living. After kicking around the underground rap landscape for years, he’s probably more famous now than he’s ever been. He’s one of the people behind The New Negroes, a musical and comedy TV show that Comedy Central greenlit last year. (Its first episode taped back in April; we don’t yet know when it’ll air.) OME also just made his pro-wrestling debut, which he says is also his last match and which means he’s retiring undefeated. As publicity stunts go, this one was glorious and life-affirming. I hope it worked. The independent hustle can’t be easy.

Just ask Milo. Once upon a time, Milo was a member of Hellfyre Club, an LA-based indie-rap supergroup, along with Open Mike Eagle. And there’s a moment on What Happens When I Try To Relax where OME shouts out both Milo and Soulfolks, the record store that Milo recently opened in Biddeford, Maine. Milo has been making music for a while now, and he’s been having a hell of a year. In January, he released Sovereign Nose Of (Y)our Arrogant Face, an album under his Scallops Hotel alter-ego. In August, Nostrum Grocers, Milo’s duo with Brooklyn rapper/producer Elucid, released their self-titled album. Both are very good. Then, last month, Milo released his own album Budding Ornithologists Are Weary Of Tired Analogies. It’s one of the year’s best rap albums.

Even compared to a peer like Open Mike Eagle, Milo is a brain-warpingly dense and insular rapper. His lyrics are full of asides and allusions, and certain lines of his — “Set it off by disagreeing with Lacan” — make me want to go back to college so that I can more properly figure out what the fuck is going on. He raps in a thoughtful mutter over broken, refracted, jazz-addled beats, many of which he produced himself. Sometimes, he loses himself in pure imagery, in the way that words fit together, even as he makes his points: “Clouded lemon tree / Solomon grew accustomed to the bowing and bended knees / The scent was heavenly,” “Time became aberrant in my other hand / Black Orpheus boogie man / How to rap with a hammer post-Scribble Jam.”

But just like Open Mike Eagle, Milo spends a good deal of his new record pondering his own role within rap, and it’s not especially rosy. Sometimes, he doesn’t trust the people who like his music: “Leave the show like ‘Milo spoke so well’ / Threaten to poke a hole through my fontanel.” Sometimes, he wonders about his own validity, or at least he takes on the voice of people questioning his validity: “Who is he but a charlatan braggart? / The nigga’s an actor, non-factor, underground hip-hop miasma.” Sometimes, he wonders why anyone would ever listen to him, “They yelling ‘Bro, you inspire me’ / Like I ain’t the nigga who said ‘Oh well’ to life’s entirety.”

And Milo’s questions are not idle. Shortly after the release of Budding Ornithologists, Milo tweeted that “Milo is officially finished” and that the album would be the last that he released under that name. Milo isn’t retiring from music. He’s said that he simply envisioned that album as the end of this particular arc: “I’ve trained myself well, I know how to execute most of my artistic ideas, I know how to get an audience, I know how to make a living off this. I’m interested in working on something now that reflects that from the genesis.” (He also says that his record store is doing well, which is pretty incredible when you consider that it’s an all-rap record store in Maine.) I hope that’s true.

Guys like Open Mike Eagle, Milo, and Serengeti are too good at making rap music to ever stop making rap music. But the music they make is so specialized and specific that I honestly don’t know how anyone can feed their kids making it. I hope they keep making it. But if they ever truly stop, if they find something else to do with their lives, I understand.

FURIOUS FIVE

1. BandGang: “License”
A step-by-step scamming tutorial that sounds a lot like “I Got 5 On It.” I shouldn’t even have to sell this.

2. Powers Pleasant: “Please Forgive” (Feat. Denzel Curry, IDK, Zombie Juice, & Zillakami)
I don’t think I’ve heard a posse cut this growly and incoherent since that first horrorcore era. That’s a compliment.

3. City Morgue: “KenPark” (Feat. Sickboyrari)
One of these days, I’m going to have to write a column about ZillaKami, one half of City Morgue and one of the key figures in a whole new wave of unhinged mosh-rap screamers. This song is named after an impossible-to-find, verging-on-porn Larry Clark movie, and it makes me want to headbutt a cinderblock into rubble.

4. Teyana Taylor: “Gonna Love Me (Remix)” (Feat. Ghostface Killah, Method Man, & Raekwon)
Teyana Taylor is only 27, but apparently she remembers how great Wu-Tang relationship-raps were, and she went and made one of her own. Meth’s Lorde reference almost made me do a spit-take.

5. The Cool Kids: “Black Mags Pt. II”
All I ever wanted from the Cool Kids was more songs that sounded like “Black Mags.”

IT WAS ALL GOOD JUST A WEEK AGO

Quality Control is leading the 2018 race of ironic label names, with GOOD Music and Cash Money Records only a marginal distance behind.

— Matt "Diet" Wilhite (@TrimHalpert) October 19, 2018