Cherry was born in Stockholm, Sweden, the son of African American jazz artist Don Cherry and Swedish painter/textile artist Monika "Moki" Cherry (née Karlsson). He is half-brother of singer Neneh Cherry, his mother's daughter, and stepbrother to singer Titiyo. He was named Eagle-Eye because the first time he looked at his father, he did so with only one eye open. As children, Eagle-Eye and Neneh spent months on the road with their father. At the age of 12, Cherry was sent to school in New York, where he stayed on to work as an actor and a drummer in various bands. In 1988, he was credited as "teenager" in the film Arthur 2: On the Rocks. In 1993 he starred on the short-lived NBC action/adventure television show South Beach.
His father died in 1995. In 1996 Cherry moved back to Stockholm to focus on his music over the acting career that had taken precedence in his professional life. He began writing and recording his debut album, Desireless, in his bedroom studio on an acoustic guitar. According to manager Tommy Manzi, Cherry's perfectionism made him keep the recordings under wraps until the album was virtually complete. The album became a commercial success throughout the world during 1998 and 1999. Desireless went platinum in the United States, selling a total of four million copies worldwide.
Cherry co-wrote and sang on "Wishing It Was" on Santana's 1999 album Supernatural, as well as in films such as Wim Wenders' The Soul of a Man, Y tu mamá también, The Love of the Game, GO, Best Laid Plans, Holes, Billy Elliot and Over Her Dead Body. Some of his best known songs include "Save Tonight", "Falling in Love Again", "Are You Still Having Fun", "Long Way Around", "Feels So Right", "Skull Tattoo" and "Don't Give Up".
On November 27, 2012, he appeared as musical guest on The Voice of Romania.
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