Pellow began his career as a solo artist in association with
Chris Difford of
Squeeze. The two met while they were patients in
The Priory in March 1999. Difford subsequently became Pellow's lyricist and unofficial helper. In November 1999, Pellow began his first solo tour. On 4 June 2001, he released "Close to You" from his debut solo album,
Smile. A further single, "I've Been Around the World", was released that November; towards the end of the year he embarked on a seven-date tour (the
Smile Tour) around Britain. In 2002, he hosted and sang in ''Girls' Night Out
, one of a week of shows in aid of the Teenage Cancer Trust, at the Royal Albert Hall. This led to him, in 2002, being offered the part of Billy Flynn, the lawyer in the musical Chicago'' in London's West End and, in 2004, on
Broadway. In May 2010, Pellow released his fourth studio album,
Devil and the Monkey, to coincide with a seven-date arena tour with George Benson, performing songs from his new album as well as hits from his solo and Wet Wet Wet career. In 2011 he released
Love To Love album, a fully orchestrated and romantic tribute to his favourite love songs that saw Pellow back in the UK charts, as well as starring in a touring production of Broadway musical
Jekyll & Hyde, beginning in January at The Churchill Theatre, Bromley, and ran to the end of July 2011. On 17 August 2012, Pellow performed his new concert show Boulevard of Life with the RTÉ Concert Orchestra at Dublin's National Concert Hall. The conductor for the show was
Fiachra Trench, a previous collaborator. It showcased songs from his 30-year career, both with the band and from his work in musical theatre. He performed the role of The Sung Thoughts of the Journalist in the 2012–13 arena tour of
Jeff Wayne's Musical Version of The War of the Worlds – Alive on Stage! The New Generation. Pellow appeared as Che in
Evita on tour around the UK in 2013, and subsequently reprised the role in a limited-run West End production of the musical from 15 September 2014 at the
Dominion Theatre. Pellow played the narrator in
Willy Russell's
Blood Brothers at Hastings White Rock Theatre between 23 and 28 March 2015. In 2021, he confirmed the release of new single "These Are the Days" and album
Stargazer. ==Personal life==