He is best known for his portrayal of Uncle Clifford on the Starz drama series P-Valley, an adaptation of the Katori Hall play Pussy Valley, in which Annan originated the role.

[3] He wanted to pursue acting from a young age and studied improv and theater from youth.

[7] In 2009, Annan's friend recommended him for a role in Pussy Valley, a play by Katori Hall centered on a strip club in the Mississippi Delta.

[2] He developed a detailed backstory for the character and portrayed the role in several smaller runs as well as the full production at Mixed Blood Theatre in 2015.

[2] When the play was ordered for a television adaptation by Starz, Annan again auditioned for the role of Uncle Clifford and was re-cast.