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He began presenting on The Saturday Show in 2002 when he was a virtual unknown, but went on to host other shows like Xperimental and Hard Spell Abbey, as well as becoming a regular presenter in the CBBC studio and guest host of The Big Toe Radio Show on digital radio station BBC 7. Simon was the longest serving presenter of the The Saturday Show and in the 2004 summer run was the object of the game Gunge Grant in which he competed in a quiz each week with a child contestant, resulting in the loser being gunged. This game was changed slightly in 2005 and renamed Gunge GBH (Gunge Grant, Bell or Humphrey), with the new rule of a different Saturday Show presenter going head to head with the child each week. Simon was also the original host of Top of the Pops Saturday along with Fearne Cotton, which led him to present Top of the Pops. He also appeared in the CBBC Scotland detective show Suspect, where a team of three children attempt to solve a crime committed in the so-called Kilcrammond House Hotel. In 2006 he appeared in BBC One's Celebrity MasterChef and the BBC's Making Your Mind Up as southwest England's regional host. On 1 December 2006, he presented in the CBBC studio for the final time.
He is a regular voice for BBC America and voice over artist for many adverts including Crayola and McDonalds. Simon hosted a series of Movie Specials for ITV including Ratatouille: Serving up a Feast, a behind the scenes look as smash hit animation Disney Pixar Ratatouille. He also presented Hannah Super Fan for Disney Channel.
As an actor he has performed in fringe theatre around London, including at The King's Head Theatre in Islington. For CBBC Scotland, he appeared in the drama series Jess the Border Collie. Simon played the Owl in the Children's Party at the Palace The Queen's Handbag a celebration at Buckingham Palace to mark The Queen's 80th birthday directed by Sir Trevor Nunn. He also appeared in pantomime Cinderella in Torquay over the 2006 and 2009 Christmas periods and as Buttons at the Grand Opera House York in 2007 and at the Kings Theatre in Southsea.
In 2008 he featured in a run of the Guinness World Record holder for longest running live sketch comedy show NewsRevue at the Canal Cafe Theatre in Little Venice, London. He has also twice directed the show. In 2009 and to acclaim in 2010 over the election period.
He has starred in an advert for online insurance and holiday finders 'Money Supermarket.com' and recently took a role in Emmerdale.