2006–2015: Early work 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. 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.
2016: Moonlight 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. Holland's performance was singled out by some film critics, including those at
Rolling Stone and
GQ, who dubbed him a "standout" in the film. As a member of the film's
ensemble cast, he received a nomination for
Outstanding Performance by a Cast in a Motion Picture at the
23rd Screen Actors Guild Awards. He also received nominations for
Best Supporting Actor from the
Florida Film Critics Circle and
Outstanding Supporting Actor at the
Black Reel Awards.
2017–present (right) promoting
The Dutchman at
South by Southwest 2025 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. Holland starred as the lead role in
Duke Johnson's 2025 film
The Actor, based on the novel
Memory by
Donald E. Westlake. ==Filmography==