Shifting between styles with deftness, Alabama's elusive Pink Siifu found underground success in the late 2010s with his experimental blend of genres. Piecing together aspects of his wide-ranging influences, the prolific rapper/singer and producer built an extensive catalog during the 2010s, releasing a total of 46 EPs, albums, and mixtapes throughout the decade. Siifu has been no less busy in the 2020s with projects such as Negro (2020), Gumbo'! (2021), and Real Bad Flights (2022) expanding his body of work.

Born in Alabama and swiftly moving to Cincinnati, genre-warping musician Pink Siifu (born Livingston Matthews) got his start in music as a drummer in his high school's band. Quickly developing a love for hip hop, Matthews dropped out of college to pursue a rap career, performing as Liv Martez in close collaboration with local talents like Young Duece and Anwalk. After moving to Los Angeles, Matthews began to develop connections in the city, with early associations including Sudan Moon, AshTreJinkins, and Conehead. Splitting into two personae using the production moniker iiye and the vocalist moniker Pink Siifu, Matthews quickly built a substantial catalog: He put out seven short projects in 2014, five in 2015, and ten in 2016. These rapid-fire releases allowed the young musician to demonstrate his versatility, moving between warped ambient (Zen), sample-splicing jazz (Black Food 1), haunted post-dubstep (A Second Definatelycaughtin Between Love X Fear), and experimental rap (Let Go) quite deftly. Perhaps the most notable of these was 2016's Space Ghetto: originally intended as Matthews' debut album, the 24-track mixtape features everything from ambient to jazz, with Matthews dipping into the mix in a variety of vocal styles.

This prolific output continued into the late 2010s, where Matthews released a further 20 projects in 2017 and 2018. Alongside a collection of genre-bending EPs, this period saw the release of his debut album Ensley: Combining the works of Siifu and iiye, Ensley's varied palette of sonic textures and free-form instrumentation received nods from major music publications, giving the enigmatic musician his first taste of indie success. Moving into 2019, Matthews' work ethic showed no signs of slowing, with the musician releasing EPs Black Food 4, Im Still., Grden.2, and Uptwn.3, alongside the Syrup EP as part of experimental neo-soul band B. Cool-Aid.

Equally energized during the next decade, Siifu's 2020 releases included Bag Talk and FlySiifu's, projects recorded respectively with YUNGMORPHEUS and Fly Anakin, as well as the solo flight Negro, on which Moor Mother joined him for the track "Bebe's Kids, Apollo." He and Anakin connected again for $mokebreak, which along with the guest-filled Gumbo'! filled his 2021 release slate. In 2022, Siifu partnered with Real Bad Man for Real Bad Flights, a brief set highlighted by the Boldy James collaboration "Looking for Water." ~ David Crone

Equal parts music label and streetwear designer, L.A.-based operation Real Bad Man made inroads into hip-hop with their On High Alert mixtape series before taking their behind-the-boards role further with a string of collaborative LPs. Delivering nostalgic, clean boom-bap production, they found their first major spotlight with Boldy James collaboration Real Bad Boldy (2020), followed in 2022 by a second joint album, Killing Nothing.

Helmed by LA-based director Adam Weissman, fashion/music outlet Real Bad Man complimented their streetwear line with a continual stream of rap mixtapes, producing beats for new-school and veteran talents alike. Debuting in 2020 with mixtapes On High Alert Vol. 1, Vol. 2, and Vol. 3, the outfit early collaborations saw them join the likes of Blu, Flee Lord, and Roc Marciano, with a sound characterized by slick, modernizations of classic-era boom-bap. They first hit the spotlight with the Boldy James collaborative album Real Bad Boldy (2020). With the Detroit MC at the peak of his powers following albums Manger on McNichols and The Price of Tea in China, Real Bad Man complemented his blunt vocals with jazz-laden, '90s-era productions. After a brief hiatus, Real Bad Man returned in force in 2022, issuing On High Alert, Vol. 4, and collaborative albums Mood Swings (with Smoke DZA), Real Bad Flights (with Pink Siifu), and the critically acclaimed Killing Nothing (a second collaboration with Boldy). A similarly prolific output marked 2023, with the label producing LPs with Kool Keith (Serpent), Blu (Bad News), and YUNGMORPHEUS (The Chalice & The Blade). ~ David Crone