The Darkest Cloud is the debut studio album by Chicago rapper Vakill, released May 5, 2003, on Molemen Records.

The album came eight years after the rapper's 1995 debut EP Who's Afraid?.

The Darkest Cloud features production from members of The Molemen and guest appearances from Slug (of Atmosphere), Copywrite, Camu Tao, and others.

The album's lead single is "End of Days" b/w "Sickplicity" b/w "The Creed".

[citation needed] The album drew positive reviews from underground hip hop fans and critics alike, with praise for its production and lyricism.