Skrein made his directing debut by directing and writing the short drama film Little River Run which he released on 20 July 2020 at his Instagram. On 8 November 2019, he starred in Roland Emmerich’s blockbuster movie Midway, co-starring Mandy Moore, Patrick Wilson, Luke Evans, Aaron Eckhart, Nick Jonas, Dennis Quaid and Woody Harrelson. He was slated to star in the Hellboy reboot as Ben Daimio, a Japanese-American character after controversy over his casting, Skrein announced on Twitter that he was stepping down from the role in the hopes an actor of the proper ethnicity would be cast. In 2018, Skrein starred in psychological revenge thriller, In Darkness, alongside Natalie Dormer and Stacy Martin principal photography began in early 2016. In 2017 Skrein also appeared in the music video for 'Eye Contact' by Ocean Wisdom playing the bad guy. In 2016, Skrein played the lead villain, Ajax, in the blockbuster action film Deadpool. Though the film was critically panned, his performance was praised. In 2014, Skrein was cast in The Transporter: Refueled, replacing Jason Statham as the lead. Skrein states that it was not his choice to leave the show.

However, in the fourth season of the series, he was replaced by Dutch actor Michiel Huisman. Skrein portrayed Daario Naharis in the third season of the television series Game of Thrones. Skrein got his first lead role in Plan B's Ill Manors. Skrein made his acting debut in Plan B's short film Michelle.

In 2009 Skrein collaborated with rapper Dr Syntax to bring the collaborative album Scene Stealers under the name Skreintax. Later that year, Skrein released a collaborative EP, Pre-Emptive Nostalgia, with the group A State of Mind. He has collaborated with a variety of artists including Foreign Beggars, Asian Dub Foundation, Plan B, Dubbledge and Doc Brown. In 2007, he released his first album, The Eat Up. In 2004, Skrein released a three track EP under the record label Dented Records. He graduated from Byam Shaw School of Art, a public tertiary art school, with a BA Hons degree in fine art painting. He is of English and Austrian Jewish descent. Skrein was born in Camden, London, England, and was raised there and in other London boroughs, Haringey and Islington.

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