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 through the 2020s. 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 (2018's Humble Pi), with additional releases produced by Quelle Chris (2020's Don't Feed the Monster) and Illingsworth (2022's There in Spirit).

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 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 on 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.

In 2011 he signed with Stones Throw and released the Subject: Matter EP. His first full-length for the label, 2012's First of a Living Breed, featured production from the likes of Oh No, rthentic RTNC, Oddisee, and Jonwayne. Oh No was joined by Blu and DJ Spinna on the 2014 album Hallways while that year's EP, White Sands, was produced by Paul White. White returned for the 2016 LP Kindness for Weakness, which also featured production from RJD2, Georgia Anne Muldrow, and Large Professor. Just a year later, Sandman released his seventh album and fourth for Stones Throw, Veins. Humble Pi, a collaboration with Edan, appeared in 2018. Solo album Dusty, produced by Mono En Stereo, arrived on Mello Music Group in 2019. Don't Feed the Monster, a Quelle Chris-produced set containing highly personal lyrics reflecting on childhood traumas and the breakup of a long-term relationship, appeared in 2020. The Aesop Rock-produced EP Anjelitu was released in 2021, and There in Spirit, with Detroit's Illingsworth handling production, followed in 2021. ~ David Jeffries & Paul Simpson, Rovi