Kanye West "Coldest Winter" (2008)

Reportedly written about the untimely death of Kanye's mother Donda—who died while in surgery, in November 2007—"Coldest Winter" finds Kanye updating a Tears for Fears classic, pouring his heart into a reworked message via new vocals addressing her passing at the end of the already painful album (and undoubtedly Kanye's most vulnrable work to date), 808s & Heartbreak. The loss of his closest love has Kanye wondering if he'll "ever love again." Hearing "Coldest Winter," you can't help feel like it might be a very, very valid concern.