He plays a lead role on the 2020 Netflix musical drama series The Eddy, directed by Damien Chazelle.

[6] In 2010, he was cast in the Matthew Lopez play The Whipping Man,[7] for which he won the Vivian Robinson/Audelco Award for Best Supporting Actor.

[9] For his performance, he was nominated for the NAACP Image Award for Outstanding Supporting Actor in a Motion Picture.

From 2014 to 2015, he starred in a supporting role opposite Clive Owen in the Cinemax original drama series The Knick.

[10] In 2016, he achieved widespread notice for his performance as Kevin in Barry Jenkins' drama film Moonlight, for which he received critical acclaim and numerous accolades.

[16][17] Following the success of Moonlight, in 2017, Holland portrayed Youngblood in August Wilson's play Jitney on Broadway.

[20] Later that year, he portrayed the leading character Henry Matthew Deaver on the Hulu series Castle Rock; his turn on the series has earned positive reviews from critics, including Amy Woolsey of Vulture, who praised his performance as "textured.

[23] In 2022, Holland was cast as Paul Cole in Duke Johnson's upcoming film The Actor, based on the novel Memory by Donald E.