He attended Florida State University and studied abroad at the FSU London study centre during his time there. He also received a Master of Fine Arts degree from New York University in 2006.

Holland’s first on-screen performance was in an episode of Law & Order in 2006. Around this time, Holland began to perform more regularly on stage as well. In 2006, he portrayed three characters in the play Blue Door. Charles Isherwood of The New York Times gave his performance a positive review.

In 2008, he played Eric in the play Wig Out! and took his first film role in the sports drama Sugar. The following year, he portrayed Elegba and Marcus in The Brother/Sister Plays. In 2010, he was cast in the Matthew Lopez play The Whipping Man, for which he won the Vivian Robinson/Audelco Award for Best Supporting Actor.

In 2011, he starred as Julian “Fitz” Fitzgerald in several episodes of the NBC sitcom Friends with Benefits. In 2013, he portrayed Wendell Smith in the film 42. In 2014, he portrayed Andrew Young in Ava DuVernay’s historical drama film Selma. 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.

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. The film won several Academy Awards, including Best Picture, at the 89th annual ceremony.

Following the success of Moonlight, in 2017, Holland portrayed Youngblood in August Wilson’s play Jitney on Broadway. He next appeared in DuVernay’s fantasy adventure film A Wrinkle in Time, released in March 2018. The film received mixed reviews from critics. 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.”

Since July 2018, he has starred in a production of Othello at Shakespeare’s Globe, costarring with Mark Rylance. In 2018, he also made his Off Off Broadway directing debut with a production of Greg Keller’s Dutch Masters.