As a teenager he became interested in recording and hip hop, spending much of his free time in the studio and participating in Jacksonville's music and arts scene.

After graduating from Orange Park High School, he took a job as a flight attendant for American Airlines, which allowed him to participate in poetry slams across the country.

[3] Letson began writing plays and acting, and in 2001, he produced his first one-man show, Essential Personnel, in Jacksonville.

[1] His solo show Summer in Sanctuary opened Off-Broadway at the Abingdon Theatre Company in 2011 [7] In 2007, Letson produced a short film which he released on the internet.

[13] In 2021, he hosted a radio show Mississippi Goddam: The Ballad of Billy Joe (nominated for Peabody Award).

During a Berkeley, California "Rally Against Hate" demonstration that he was covering, Letson saw five masked protesters beating an unarmed man with sticks.

[15][16] Fearing for the man's life, Letson used his body as a human shield and encouraged the protesters to discontinue their attacks.