[2] Before going to university he was a keen amateur actor, appearing in the Crescent Theatre's musical production of Mary O'Malley's Once A Catholic and Sandy Wilson's The Cheese.
Chiles' experience from Financial World Tonight led to him fronting the BBC Two business show Working Lunch, where he came to popular notice.
[7][8] His final show also saw video tributes to an emotional Chiles from Prime Minister Gordon Brown and political leaders David Cameron and Nick Clegg.
In July 2016, he presented a special edition of Panorama called "Why We Voted to Leave: Britain Speaks" for BBC One.
On 1 January 2019, he hosted a follow-up programme on BBC Radio 4 called Brexit: bewitched, bothered or bewildered?
[18][19] The programme was commissioned by the BBC's Religious department, and saw him interviewing Oti Mabuse, John Simpson, and Martin and Shirlie Kemp.
[20][21] When the BBC won back the rights to Premier League football highlights, Chiles became the host of Match of the Day 2 on Sundays.
He was also a member of the BBC's World Cup presenting team, often bringing viewers late night highlights.
After news media speculation suggesting that the BBC wished to increase the popularity of The One Show on Fridays by introducing Chris Evans alongside Christine Bleakley in an extended one-hour format, Chiles was said to be discussing a contract with ITV.
After Evans was confirmed as the new Friday presenter in a revamped one-hour format, Chiles left the BBC for ITV in a four-year contract golden handcuffs deal worth £6 million over four years ending on 20 April 2014.
[29] In his early career at the BBC, Chiles became an assistant producer; by 1993, he was presenting Radio 4's Financial World Tonight.
In February 2019, Chiles began writing a twice weekly column at The Guardian[30] focused on subjects that Gabriella Paiella of GQ called “the banalities of everyday life” and “a gentle and delightful respite from the daily cesspool of takes and terrible news.”[31] The column features headlines like We can go to the moon – so why can’t we stop my glasses sliding down my nose?,[32] Who are these people who love to feel sand between their toes?
The wild garlic smelled lovely, but I didn’t want to die there,[35] I found a witch supply store opposite a Nisa Local.
[40] Chiles wrote the non-fiction book The Good Drinker: How I Learned to Love Drinking Less, published in October 2022.
[citation needed] On 23 November 2009, Chiles released a 2 Good 2 Bad: The World Cup DVD based on the popular segment from Match of the Day 2.
[46] In 2020, he participated in Iaith ar Daith ('Language Road Trip'), a show for S4C where he and several other celebrities learned Welsh, broadcast in April 2020.
[47] In 2022, Chiles appeared as a guest in the second "New Year's Treat" special of Taskmaster alongside Claudia Winkleman, Jonnie Peacock, Lady Leshurr, and Sayeeda Warsi.
Chiles married Jane Garvey, a former regular presenter of Radio 4's Woman's Hour, in September 1998 in Swansea.
In March 2008, Chiles embarked on a charity cycling trip with footballer Alan Shearer from Newcastle upon Tyne to London via West Bromwich for Sport Relief.
[62] In 2010, Chiles grew a beard,[63] which was later shaved off by his One Show co-host Christine Bleakley for Sport Relief, raising £60,000 in the process.