During his time at Trinity College, he began to get noticed in bars and clubs, with a long term residency at
The Dorchester hotel, London. Stilgoe's first public engagement was at the Pizza on the Park, London in 2004. Following the performance,
Dame Cleo Laine later called Stilgoe in to perform with her and husband
Sir John Dankworth on their
Radio 2 show Live at the Stables. In 2007, Stilgoe supported
Melody Gardot at the
Queen Elizabeth Hall. His debut solo appearance at
Edinburgh Festival Fringe in 2011 with sell-out show 'One Hour!' received a five star review from
The Scotsman. With producer
James McMillan, Stilgoe recorded a new album
We Look to the Stars, released in July 2012. The album went to number 1 in the Amazon Jazz Chart on its day of release. From the album, "We Should Kiss" was released as a single in July 2012. The single was used by French shoe designer
Christian Louboutin in his showcase Fue at
Le Crazy Horse in Paris and exhibition at the
London Design Museum. In February 2014, Stilgoe released a live album
Songs on Film, which includes songs from classic American films and Stilgoe's original compositions inspired by them. The album was commercially released by Linn Records on 17 November 2014, alongside his earlier albums. Stilgoe has participated in numerous recording sessions as both a pianist and singer; including the single "Elephant" by
Alexandra Burke. A publishing contract with
Kassner Music was signed in 2012, and after a series of album releases, Stilgoe then transferred to the
Music Sales Group in 2019. His album first album with the company,
The Heat Is On! Swinging the 80s, a big band swing-inspired re-composition of 80s blockbuster themes was released in 2019. ==Comedy and radio==