Born in Johannesburg, South Africa, Flynn moved to England at the age of two and has been active in the arts since his childhood. A pair of music scholarships guided his early schooling, and in addition to playing violin, trumpet, and guitar, he also sang in the choir. He later nurtured his acting abilities at London's Webber Douglas Academy of Dramatic Art. In spite of his classical training, Flynn had a deep fondness for folk and blues music and developed a rugged and propulsive fingerstyle that has become a staple of his dynamic approach.
His professional career as an actor preceded his musical rise, but after a few years of television roles and Shakespearian theater, he earned a record contract with the Vertigo label and recorded 2008's A Larum. Backed by his group the Sussex Wit (which also includes his sister Lillie Flynn), the album was a significant critical success and earned favorable comparisons to classic U.K. folk-rock like Fairport Convention and Bert Jansch. An EP followed in 2009 as Flynn became associated with the rise of indie folk and specifically Britain's nu-folk revival, touring alongside acts like Laura Marling and Mumford Sons. In truth, his music was more nuanced and layered than much of what the scene produced, and over subsequent albums like 2010's Been Listening and 2013's Country Mile (both released on the Transgressive label), he outlasted the tag. During this period, he and the band also composed the score of the 2011 indie film A Bag of Hammers.
While starring in the romantic comedy series Lovesick, Flynn was given the opportunity to contribute the theme song to another television program in BBC Four's gentle comedy Detectorists. His poignant theme song proved to be one of his most popular tracks and elevated his musical status in advance of 2017's excellent Sillion. Shifting back to acting, Flynn took on a number of period pieces including roles in a serial version of Vanity Fair and a film adaptation of Emma. He also starred as David Bowie in 2020's Stardust, a biopic focused on Bowie's pre-Ziggy Stardust period. For his next album, Flynn and acclaimed nature writer Robert MacFarlane collaborated on a set of original songs. Released in early 2021, the resulting Lost in the Cedar Wood was one of Flynn's loosest and most intense recordings. ~ Timothy Monger, Rovi