Miles Winter Roberts

Miles Winter Roberts is an English singer-songwriter and performer who is raised in Ibiza from the age of five after being born in the United Kingdom. His early life is shaped by a Balearic, beach-oriented upbringing, and he develops a reputation for colourful clothing, windsurfing and teaching the sport in a relaxed, non-competitive way.

Early life and work in Europe

Roberts spends nine years in Hamburg, where he learns another language and travels widely, including to Turkey, Poland and Russia before the fall of the Berlin Wall. He also wins songwriting competitions broadcast to a very large television audience through Intervision, described as the communist counterpart to Eurovision.

After a difficult period in Hamburg, he moves to London in 1994 and begins gigging there. His work at this stage leans towards a Balearic blues sound, using Spanish guitar and Feliciano-style vocals, and is described as strongly Mediterranean in character.

Recordings and releases

In 2000, he releases his first live CD in London on his own label, Chocolate Box. Around this time he builds a loyal following through live performances. Notable shows include appearances at the Jazz Café, The Bull’s Head with his own seven-piece band, Café de Paris as a trio, and Café Royal, where he supports Alan Price.

Through Penni Pike, who works as Richard Branson’s executive PA, he is introduced to producer Steve Brown, and a working relationship begins. Rocco Gardner later forms an independent label and backs the project, with Winter Roberts established under Sidewalk 7 and Brown, known for work with Wham, The Cult and Manic Street Preachers, handling production.

Recording begins in April 2005 and the band expands to 12 pieces. The first EP, Escapado, appears by mid-summer and gains attention internationally, including in New York, San Francisco, Los Angeles and Thailand. The release leads to performances in New York at The Cutting Room and a label launch in London.

He sells out Ronnie Scott’s on Sunday 8 January, and BBC Radio 2’s Steve Wright plays his track on air. Dave Lee Travis also invites him onto his BBC 3 Counties Sunday morning show on 12 March, where he chats and performs live in the studio.

Head in Your Cloud is released on 20 March 2006. After this, plans for the album change and he decides to record it live from scratch in front of 200 people at The Bedford in South London. The album is recorded on 21 May and mixed with minimal editing by Steve Brown. It is made available as a download from his website.

He later becomes involved with The Big Issue after performing at the vendors’ Christmas bash. A free download is arranged for the magazine and becomes the beginning of a weekly feature. He is the founding artist for Don’t Lose Your Home, a song written during his difficult years in Hamburg, and it is recorded live on the same day as the album.

Daymaker is due for release on 4 September 2006 but is also made available as a download from the website. Another track, Sha La La La in My Life, follows Head in Your Cloud, receives heavy playlisting, and is released as a download-only track on 24 July. He performs on BFBS1 in Gibraltar and undertakes a radio tour of the British Isles after regional airplay.

Style and reputation

Roberts is associated with an upbeat, island-influenced sound, and his live performances are central to his career. His music combines Mediterranean and Balearic elements with acoustic and blues inflections, and his recordings are often presented in a live setting rather than heavily edited studio productions.