As much as the surprise-release is exciting, Third Side of Tape is also bittersweet, since its liner notes finally name and give a release date to the boxset that will likely mark the actual end of Lil Ugly Mane’s career: Oblivion Access, out this June. You want to look forward to it, but you also don’t.

Before he went even more underground, in 2013, Lil Ugly Mane only ever gave a handful of interviews. One was to Mishka, who he told, “Making the cover is the best part of making music. I feel like I've started projects in the past just cause I had made a cover and wanted to use it for something.” It’s understandable, then, that during his quiet period, he continued releasing installments of a clothing collaboration with Thunder Zone, the label run by the Milwaukee rap-rocker Juiceboxxx. Their takes on hip-hop couldn’t be further apart, but they’re an illuminating pairing: Juice is another guy with a deep catalogue of idiosyncratic music, and interest in noise music, and he partakes in a similarly doomed kind of introspection. On the outro to a Juiceboxxx tape released the same year as Lil Ugly Mane’s “Evil Deed,” Juiceboxxx shouted over the horns from an SNL credit sequence, “I don’t know what the fuck I’m going to do next, man. Maybe go to college, start calling myself John… Rewind the tape, start over.” He’s still releasing music, but not without sprinkling in songs like this spring’s “Might Stop Rapping (Might Get a Real Job).”

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For both of these guys, it’s easy to see how the business of art can feel like a dead end. For every year that passes, being a 30-year-old rapper seems less appealing; it’s unfortunate and backwards, but an artist is rarely more commercially valuable than when they’re new. At times, the whole economy of new music feels like planned obsolescence. And so it is that, like the cult electronic pop duo Air France, who published a letter of retirement after collapsing under the weight of the pressure to make an album that felt original, or the blog Hipster Runoff, which self-combusted after too much self-analysis, Lil Ugly Mane is making the winding-down of his career a commentary about its own non-viability. Listening to the disparate Third Side of Tape, you’re sort of forced to compare your own rolodex of reference points to Lil Ugly Mane’s. In my case, it makes me feel like I know nothing. It’s hard to imagine him going creatively bankrupt. So maybe I’m being crazy, and overlooking the lamer and self-satisfied aspects of his whole drawn-out exodus, but I really like to think that Lil Ugly Mane’s quitting is about what he says: how incompatible his arty vision of rap was with the reality of releasing music, even if that’s just personal stress when a few thousand strangers start having expectations of you.

Beyond the announcement of Oblivion Access, the liner notes to Third Side of Tape call back to “Evil Deed.” He says that “I Quit” by The Descendents is a better song, and that had he listened to it first, he “would have probably just posted a YouTube version of that song and a link to the Google image results for ‘Dalai Lama laughing’ rather than spending any time whatsoever making my own song.” Like a lot of Lil Ugly Mane’s stuff, that's funny and sad, and it’s a joke I'm still glad he made.