But, Henley has said, "On the bus from 45th and Quintara to Mason and Geary, it hit me...You know what, I guess this guy wants me to memorize this stuff.

His early stage work included appearances with the San Francisco Mime Troupe, and a performance as "Factwino.

[2] He portrayed Crockett and Tubbs' boss Lieutenant Martin Castillo in the movie version of Miami Vice in 2006.

In 2011 he appeared as the murderer in the Body of Proof episode "Letting Go" and in 2012 he reunited with Michael Mann for the TV series Luck, playing a parole officer.

In 2019, Henley joined the cast of Agents of S.H.I.E.L.D., part of the Marvel Cinematic Universe franchise, as Marcus Benson.