Question: what is the saddest rap song?
Answer: Vince Staples “Summertime” (2015)
Future “Perkys Calling” (2016) ... 
Lil Wayne “I Feel Like Dying” (2007) ... 
Company Flow “Last Good Sleep” (1997) ... 
Earl Sweatshirt f/ Na'kel “DNA” (2015) ... 
Meek Mill f/ Young Thug “We Ball” (2017) ... 
Chance the Rapper “Acid Rain” (2013) ...