First released in 1999, Operation: Doomsday is widely considered one of the most influential albums in hip hop history. The debut studio album from the enigmatic, metal-mask-wearing British-American East Coast rapper, Operation: Doomsday is significant in that it marks the artist's first move into solo work, following previous releases as part of the group KMD. Featuring Doom's signature intricate wordplay, cartoon samples, lo-fi production values, 80s soul vocals, smooth jazz loops, and vintage drum breaks, this album draws on the weight of the artist's personal tragedies with frank lyrics and piercing rhymes. This is the release that makes it undeniably clear why MF Doom has regularly been lauded as the crucial player of underground and alternative hip hop in the 2000s.