LOS ANGELES trio clipping. are the latest anomalous group recording for that unlikely incubator of outsider hip-hop, Sub Pop. As home to intergalactic explorers Shabazz Palaces, South African "Township Tech" artist Spoek Mathambo, and the now-defunct astral soul sisters THEESatisfaction, the Seattle label best known as grunge champions in the 1990s and for nuanced indie rock in the 2000s has also nurtured adventurous rap artists during the past decade. To date, Sub Pop has released two clipping. albums, providing a substantial platform for music that colors way outside the lines of modern hiphop.

On 2016's Splendor & Misery and 2014's CLPPNG, producers Jonathan Snipes and William Hutson fuse rugged, abstract beats with the sort of sculpted noise and bizarre percussion timbres that sound more like the domain of avant-garde alienators than of RZA and J Dilla disciples or Metro Boomin. MC Daveed Diggs—who's won Grammy and Tony Awards for his work in the popular musical Hamilton—spits verses that encompass turbulent street life and robust, youngblood horniness, although bolstered by an undercurrent of existentialism. Post-gangsta anecdotes told at a PhD level, in a sense.

Sonic eccentricity dominates clipping. tracks. "Dream" consists of a bell tolling and faint, sluggish funk beats topped by a dazed recitation of kush-inspired poetic visions. On "Or Die" (as in "get money or die"), Diggs literally sounds like he's in a war zone as he raps. "Get Up" uses pitched-up EKG beeps for percussion. And has any other hip-hop group had the audacity to remix John Cage? No. Rest assured, XXL won't be putting clipping. on its cover anytime soon.

Clipping. describe Splendor & Misery as a concept album about the "sole survivor of a slave uprising on an interstellar cargo ship, and the onboard computer that falls in love with him." Once again, clipping. rise to the unusual subject matter's challenge with stark, dystopian productions that will appeal to fans of horror-obsessed noisemongers like Pharmakon and Wolf Eyes. That it's a party-wrecking record rather than a trove of radio-friendly or club-ready bangers seems of no concern to clipping. (or to Sub Pop, for that matter). This is high art that will someday be studied in universities.

Outside of Sub Pop's advocacy for form-breaking hip-hop, a handful of creative outlaws have shrugged off hip-hop's orthodoxies to forge unique canons that deserve to be more than mere footnotes. While all musical styles feature a high degree of imitation, hip-hop has shown a notable proclivity for replicating what's hot at any given moment. Therefore, respect to artists like clipping., Shabazz Palaces, et al. who shoulder-check rap further to the left, taking sonic and lyrical risks. Beyond clipping. and their Sub Pop counterparts, let's survey some of hip-hop's more notable outliers.

New Jersey trio Dälek have forged a gripping catalog of conscious, doomsday hip-hop from the detritus of noise rock, shoegaze, metal, and drone while still privileging the boom-bap. Extrapolating from Company Flow's militant aural and verbal attack, Dälek produce overwhelming mushroom clouds of cacophony over which MC Dälek seethes about myriad injustices with barbed-wire bars that would make Rakim proud. (Instructive track title: "A Collection of Miserable Thoughts Laced with Wit.") Whether sampling Beat icon William S. Burroughs or collaborating with kraut-rock legends Faust and British triphop brutes Techno Animal, Dälek prove they're one of the most uncompromising units ever to be filed under "hip-hop."

The rare rap crew signed to boundary-pushing UK electronic label Warp, Antipop Consortium boasted three hyper-smart MCs—Beans, High Priest, and M. Sayyid—who also made radical beats, with help from Earl Blaize. This trio of lyricists offered existentialist, surrealistic, and sporadically comedic flows, tying your brain in science-fictional knots while the music found new methods to freak the funk out of its blues. (Instructive track title: "Disorientation.") You can't go wrong anywhere in Antipop's discography, but don't overlook their masterly summit meeting with Anglo-Russian DJ Vadim under the name the Isolationist. Furthermore: Horny genius Beans's solo career is also dynamite.

Divine Styler's Spiral Walls Containing Autumns of Light remains one of golden age hip-hop's ultimate WTF? releases. Released in 1992 on Warner Bros. subsidiary Giant, the album unsurprisingly sold poorly, but it attained cult status among non-purist hip-hop fans and other weird mofos. The record's mélange of heavy-lidded R&B, psychedelic funk, mellow folk-rock, sci-fi-flick soundtrack passages, and meta-spiritual spoken-word madness makes it a sui generis genre bender that sounds like what Prince might have conjured after massive DMT ingestion. (Instructive lyric: "Hell's afraid I will take over.") The world needs a vinyl reissue of Spiral Walls stat.

No overview of rap outsiders would be complete without an entry from the anticon./Mush collective. And cLOUDDEAD represent the zenith of those renegade labels' output—particularly their self-titled 2000 compilation LP. Taking cues from their name, cLOUDDEAD—Dose One, Odd Nosdam, and Yoni "Why?" Wolf—suffuse their cryptic lyrics in murkiness and mystique, while the music predates cloud rap's penchant for ambient drift and dream-logic atmospheres by more than a decade. Their sample of the profoundly melancholic Mellotron part from the Moody Blues' "Nights in White Satin" in "I Promise Never to Get Paint on My Glasses Again" epitomizes the group's über-nerd subversiveness. Amid a verbose stream of consciousness, the words "In accordance with my weird ordinance/My style is glass cutter, delicate/intense" stand as an apt self-critique. Don some headphones and get lost in cLOUDDEAD's labyrinthine torrent of grad-school-poetic language.

Honorable mentions: Dr. Octagon, Prince Paul, New Kingdom, Company Flow, Edan, Ursula Rucker, Basehead, Deep Puddle Dynamics, Death Grips, Cannibal Ox, Spectre, and Busdriver.