In 1999, Scott entered the nationwide British Resorts Association Search for a Star Contest, which was sponsored by the Southern Daily Echo.

When Scott appeared in the semi-final at the Bournemouth Pavilion he received best speciality award, the Stan Sowden Memorial Trophy, £500 cash, the judges' and the audience vote.

[9][10] The national final saw Scott take first prize, and collect a trophy, a cheque for £2,750, a voucher for a £400 costume, and entries in two stage publications, again winning the audience vote and best speciality act award.

Scott was spotted by music promoter Derek Nicol after he won Southern Daily Echo Star Trail and went on to represent Bournemouth at the British Resorts Association national final in Leamington Spa.

His act brought a different monkey puppet, named Stephen which he performed the song "No Matter What" by Boyzone, when Scott started singing as himself, Cowell hit his buzzer.

[17] After the semi-final in her Daily Mirror column Amanda Holden went on to say "In the auditions Monkey Boy was my top choice one of my personal favourites.

Scott was invited to the Grand Order of the Water Rats Annual ball 2007 as a guest in the Great Room of the Grosvenor House Hotel in London, and was delighted to not only be nominated for the 'Serge Ganjou Award' but to win it and collect the £4,000 prize.

[20] After the show, Damon performed at Amanda Holden's wedding to Chris Hughes held at Babington House, Somerset, on 10 December 2008.