Thanks to his inventive flows, literate lyrics, and dry sense of humor, Homeboy Sandman emerged as one of the most original, prolific underground rappers of the late 2000s and 2010s. With verbal styles ranging from vitriolic screeds to stilted stream-of-consciousness narratives, his songs often criticize the conventions of hip-hop, in addition to examining societal issues and lighter subjects such as the joy of healthy eating. After making a name throughout the underground New York hip-hop scene with independent releases such as 2008's Actual Factual Pterodactyl, Sandman received wider exposure when he signed to California's Stones Throw label during the early 2010s and released acclaimed albums such as 2012's First of a Living Breed and 2014's Hallways. Sandman has also released collaborations with Aesop Rock (several EPs beginning with 2015's Lice) and Edan (Humble Pi).
Angel Del Villar II was born to a boxing father who emigrated from the Dominican Republic to New York and fought on the heavyweight circuit. Retiring undefeated, Del Villar's dad then went to law school to become a community lawyer, a path his son would follow for three years before dropping out. At first, he was to become a teacher, but just moonlighting as an MC wasn't enough, so with the 2007 release of his debut EP, Nourishment, he went with hip-hop full-time. After Nourishment 2 (Second Helpings) expanded the EP to album length, his official debut album, Actual Factual Pterodactyl, followed in 2008. DJ Spinna and Ski Beats would both lend a hand to his 2010 album, The Good Son, released the same year that Sandman would be featured as an aspiring rapper's mentor on the MTV reality television series Made.