As well as touring with Tom, much of Winston's early career saw him composing music for, and performing in, London-based contemporary theatre productions.

In 2012, Winston contributed the track "This Wheel's on Fire" to the compilation CD set for Amnesty International titled "Chimes of Freedom – The Songs of Bob Dylan".

[8] On 10 November 2011, the track "She Went Quietly" was used over the ending of the mid-season finale of Grey's Anatomy (Season 8, Episode 9 "Dark Was The Night").

In 2008, his cover of The Spencer Davis Group song "I'm a Man" appeared on a television advertisement for Volkswagen Polo.

The ad featured a dog miming the words to the track,[9] and received over 750 complaints from the RSPCA and TV viewers.

[13] His elder brother, Tom Baxter,[14] and younger sister, Vashti Anna, are also musicians and all use their middle name as a stage surname.