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 Stones Throw and issued acclaimed albums such as 2012's First of a Living Breed and 2014's Hallways. Sandman has also released collaborations with artists like Aesop Rock, Edan, Quelle Chris, and Illingsworth. His solo effort 12 Days of Christmas & Dia de Los Reyes appeared in early 2023.