Jay-Z "Lost One" (2006)
The first two verses of this track don't address death. Instead, Hov opts to take his time and discuss the matter of partnerships gone sour (he might be referring to Jaz-O, but our money is on Dame Dash) and the second verse is about the brief period Jay-Z and Beyonce broke up (say it ain't so, Hov!). But then he gets to the emotional third verse, where Jigga recounts giving a car to his nephew, who then later died in a car crash. Easily one of the most somber songs of Jay's catalog, some things—like this track—are worth losing a little sleep over.