Tom Breihan of Pitchfork gave the album an 8.3 out of 10, calling it "a harrowing ride on which Cage describes his childhood in fractured blips of vivid images instead of broad, sweeping statements."[11] Ross McGowan of Stylus Magazine gave the album a grade of B−, saying, "Hell's Winter has its moments, but while the production is noteworthy, the actual songs within are rather hit or miss."[14]
Exclaim! named it the 9th best hip hop album of 2005.[15] In 2010, Rhapsody included it on the "10 Best Albums by White Rappers" list.[16]