Hawkins attended Thornton High School, where he initially played basketball. Influenced by his grandfather’s advice to “choose what makes you feel better,” Hawkins left the basketball team sophomore year and joined the speech team, where he became a two-time state champion. In 2005, Hawkins won the state title in the Illinois High School Association's Original Comedy event, also placing third at the IHSA state competition in Humorous Interpretation. In 2006, he and a partner won the state title in Humorous Duet Acting, while Hawkins also placed fourth at state that year in Original Comedy.
