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A Chicago Story // Chief Keef and Tobi Lou Got Each Other Back in their Experimental Bags

Evan Dale // July 18, 2023

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Tobi Lou

At the center of the NBA offseason stage, Damian Lillard — who occasionally daylights under his rap moniker, Dame D.O.L.L.A. — is somehow finding time while maneuvering his way through the trade gauntlet to drop a verse on Tobi Lou’s first (public) album of the year. It’s a verse that the Chicago rapper has half-jokingly said he kept short so as not to be outshined even further by the point guard who legitimately — and not just from the perspective of the classic tale that an NBA player embarrassingly turns wannabe rapper for a Summer — has bars. And even so, Lillard’s feature on Tobi Lou’s new project is not the most unexpected one. Instead, it’s Tobi Lou’s vivacious creative chemistry with fellow Chicago enigma, Chief Keef, that steals the show.

Tobi Lou is prolific. A product of the internet rap era that he — the owner and operator of an app, TobiLoop, where he releases extensive (and expensive) additional content to his canon — is certainly a proponent of, he’s never long without his presence being felt in some way. Musically, that means a lot of projects, though rarely an album - or at least one for the masses (Baggy Weather was released to his app earlier this year). Before that, it was the bass-heavy Non-Perishable in 2022, and the marathonic Live On Ice in 2019. But, if we’re all being honest, nothing like the bubble-rapped, creatively dynamic, inventive, and ultimately experimental run of early EP’s: Tobi Lou and the Moon, and the Loop, and the Juice, has made itself felt throughout the course of a full-length project since. Until now.

Chief Keef is kind of an open mystery. The most influential force of a Chicago Drill renaissance that swept around the world at his behest after the release of Finally Rich in 2012, it’s not as if he’s suddenly stopped making music after it. But, has anyone really been listening? The answer to that question is not a fault of his own. Sosa was the victim of early internet rap fame where his absolute explosion into the stratosphere of international recognition, also meant that he was simultaneously frozen in time and memefied. Love Sosa, Hate Being Sober, and Don’t Like are still - and always will be - his most popular tracks; the core to his identity from an outsider’s perspective. Most people haven’t been keeping up unless they’re reliving their former glory through a decade’s ago lens. Until now.

Tobi Lou

It’s not on one track, but two, where Tobi Lou and Chief Keef link during ‘Decent. And something about their collision of sounds, of energies, of narratives feels propelling for both artists. Both Chicago rappers who led a subgenre shift that skyrocketed them to recognition; both unique characters whose internet presence feels as documented by forces outside of music as it does by the force they hold within it; both trailblazing creatives who seemingly need a little spark to unearth something new for themselves at a time when audiences always want to hear the same old signature. Both, together, radically new for themselves, creating again, as they once did: freely.

There must have been some mutual inspiration when they stepped in the studio alongside one another. There is of course recognition from each that the other is a major player in their city, and in their soundscape. And together, overtop the solemn, acoustic beat of Forecast, they change both of their narratives by thriving on something more experimental than either of them have delivered since their explosions from the underground sent them soaring to new heights with only one direction to fly in.

But now, thanks to their mutual presence alongside each other on Forecast and Hit & Run (which we’ll talk again more in depth about shortly because it’s Chicago’s newest, truest Summer anthem) they beaming in myriad new directions again.

Weaving in the signature flow of fellow Chicago rapper and profound lyricist, Saba, hand in hand with the changes of pace that production from inernetboy leaves on a beat, makes the compositionally vast landscape of Hit & Run particularly plentiful for both Tobi Lou and Chief Keef — who take on a quickfire verse and an anthemic hook, respectively — to find firm footing ion the experimentation.

There’s a case to be made, that even if each artist had rediscovered a taste for the experimentally nuanced and altogether new, that without one another’s mutual presence, this moment wouldn’t have been noticed in the way that it is. There are a lot of Tobi Lou fans who didn’t even know he was releasing a project because so much emphasis had been relegated to his app over the course of the year to date. Chief Reef’s presence however, turned all their heads.

There are a lot of Chief Keef fans still rinsing his old work, where a focus on drill changed the hip-hop landscape a decade ago. But they haven’t tuned in to see what he’s been doing with his time lately: evolving, as all artists do. But working with an experimentally founded, unique Chicago name like Tobi Lou caught them by surprise and got them on board, too. When fans on both sides — or fans of both, as likely persist through the powerhouse Chicago hip-hop scene — did in fact tune in, everyone is being taken aback by how much sonic evolution is occurring for both artists when they collaborate. They seem like their old selves again, albeit new at the same time.

Mutually, Tobi Lou and Chief Keef got each other back in their experimental bags, and ‘Decent is far more than decent because of it. Reminiscent to the self-aware, uncaring, art school projects that Tobi Lou used to put out, 'Decent is also radically new, even when weighed against the 2018 version of himself. Whether or not the Chief Keef collaborations brought you here, definitely take the time to time to listen to the whole thing, because it's Tobi Lou's best work in years.

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