Buffalo-born heavyweight lyricist Conway The Machine has officially announced his next major studio full-length album, OTIS, set for release on November 20th under his independent label, Drumwork Music Group. Serving as his first proper solo album since last year’s critically acclaimed You Can’t Kill God With Bullets, the upcoming project represents a significant milestone in the rapper’s prolific career. To herald the arrival of OTIS—an acronym for "Often Times I Suffer"—Conway has dropped the album’s aggressive lead single, “Diggwutumsayn!,” alongside a cinematic accompanying music video directed by Marques Mosley.
The announcement comes on the heels of a relentless period of activity for the Griselda co-founder, who spent much of the past year touring internationally, celebrating milestone anniversaries of classic underground projects, and nurturing talent on his Drumwork imprint. With an eclectic slate of guest features that spans legendary East Coast hip-hop royalty, underground stalwarts, and even mainstream rock mainstays, OTIS is poised to be one of the most unpredictable and expansive releases of Conway The Machine’s career.
Lyrical Mastery and the Arrival of “Diggwutumsayn!”
The rollout for OTIS commenced with the release of the album’s lead single, “Diggwutumsayn!,” produced by his longtime sonic architect, Daringer. The track is a masterclass in modern boom-bap lyricism, featuring a relentless double-time flow delivered over an ominous soundscape composed of haunting horror-movie strings and gently plucked acoustic guitars.
Lyrically, Conway wastes no time asserting his dominance within the contemporary rap landscape. Over Daringer’s cinematic production, the Buffalo emcee drops topical pop-culture references, mentioning rising R&B singer 4Batz and comedic actor Kenan Thompson, while celebrating international milestones, such as sold-out concert venues in South America. Most notably, Conway reflects on his financial evolution and business acumen within the music industry, rapping, “Took that $60,000 from Shady Records and turned that into $8 million.”
The accompanying music video, directed by Marques Mosley, mirrors the gritty narrative style embedded in Conway’s bars. Dressed in a sharply tailored designer suit, the rapper is depicted stalking the corridors of a local motel, meticulously working to keep his hands clean in the aftermath of a clandestine operation. The visual complements the hard-boiled aesthetic that has defined Conway’s career since his earliest underground offerings.
A Diverse and Unexpected Star-Studded Guest Roster
While Conway’s signature sound has always remained rooted in gritty, uncompromised street rap, OTIS promises a surprisingly eclectic blend of collaborators that bridges generational and genre divides. According to official tracklist and feature previews, the album will boast appearances from iconic East Coast veterans, including the legendary Kool G Rap and three-fifths of the seminal Wu-Tang Clan: Ghostface Killah, Method Man, and Raekwon.
In addition to legendary heavyweights, the project embraces the underground scene with guest verses from artists like Flee Lord and Inkredible NES. However, the most unexpected inclusion on the OTIS roster is Robby Takac, bassist and founding member of the multi-platinum, Buffalo-originating alternative rock band the Goo Goo Dolls. This crossover hints at a broader sonic palette for the album, moving beyond standard sample-heavy boom-bap to incorporate unexpected instrumental textures.
Production-wise, OTIS relies heavily on trusted collaborators who understand Conway’s stylistic preferences, chief among them being Daringer and Conductor Williams. These producers have historically provided the stark, loop-driven canvases that allow Conway’s cinematic storytelling and vivid underworld narratives to take center stage.
Chronology and Context: Building the OTIS Era
To fully understand the weight of OTIS, one must examine the rigorous timeline of releases and touring cycles that led Conway to this point. Following his departure from major distribution structures and his establishment of Drumwork Music Group as a self-contained powerhouse, the Buffalo native has maintained an unrelenting release schedule.
In late 2024, Conway delivered You Can’t Kill God With Bullets, a holiday-season release that received widespread critical acclaim from major publication outlets including Pitchfork, Rolling Stone, XXL, and Billboard. That album featured an elite roster of contributors, ranging from underground staples like Roc Marciano and Griselda affiliates to mainstream producers like Timbaland and AraabMuzik, alongside guest verses from artists such as G Herbo.
Following that commercial and critical success, Conway kept his momentum high by releasing the DJ Whoo Kid-hosted mixtape I Heard You Paint Houses. That project found the emcee aggressively tackling instrumentals popularized by contemporary mainstream titans, including Drake, Kendrick Lamar, Future, and Jodeci, demonstrating his ability to dominate any beat regardless of origin.
Over the past four years, Conway’s solo discography has expanded rapidly with a string of celebrated full-length projects:
- 2021: La Maquina
- 2022: God Don’t Make Mistakes (his major-label debut via Shady Records/Interscope)
- 2023: Won’t He Do It
- 2024: Slant Face Killah
- 2024–2025: Curating and releasing two full-length albums for Drumwork signee Jae Skeese.
In addition to his studio output, Conway spent the summer of 2025 touring extensively across Europe, connecting directly with international audiences. In the fall of 2025, he returned to New York City to headline a special anniversary event celebrating the tenth anniversary of his foundational underground classic, Reject 2.
Overcoming Adversity: The Foundation of Conway’s Resilience
Conway The Machine’s journey to the upper echelon of hip-hop is well-documented and stands as a testament to physical and mental endurance. Born and raised in Buffalo, New York, Conway survived a violent shooting incident that left him with multiple gunshot wounds to his head and neck. The trauma resulted in Bell’s palsy, which permanently altered his facial structure and speech patterns, a physical reality he transformed into a distinctive, intimidating vocal trademark rather than a hindrance.
Working alongside his brother and fellow Griselda co-founder Westside Gunn, Conway helped spearhead an underground Renaissance in the mid-2010s that revitalized gritty, sample-driven East Coast hip-hop. As an independent executive, he has successfully transitioned from an underground survivor into a music industry boss, running Drumwork Music Group with a hands-on approach to artist development and physical product distribution.
Industry Implications and Market Analysis
The arrival of OTIS carries several notable implications for the independent hip-hop market. By partnering a core aesthetic of traditional street rap with unexpected genre crossovers—such as the collaboration with Robby Takac of the Goo Goo Dolls—Conway demonstrates a willingness to push creative boundaries without alienating his core demographic.
Furthermore, the strategic rollout of OTIS highlights the sustainability of the independent-major hybrid model. By leveraging his own Drumwork infrastructure while utilizing targeted digital singles and cinematic music videos, Conway maintains complete creative control over his catalog while sustaining high levels of fan engagement.
As the release date of November 20th approaches, anticipation continues to build across the hip-hop community. With OTIS, Conway The Machine aims to reinforce his legacy not merely as a survivor of the streets or a relic of a bygone regional sound, but as an evolving, modern great capable of adapting his artistry to new sonic frontiers.
