Chris Evans has lost his case against his former station Virgin Radio over share options he said were still due to him after his sacking in June 2001.
Evans' new TV show has had a shaky start
After several months out of the spotlight, Evans made a faltering return to primetime Saturday night TV this year as producer of the poorly received Boys and Girls.
The Channel 4 game show, billed as the ultimate battle of the sexes, won just 5% of the audience on its debut - and was mauled by the critics.
Despite the trademark Evans brashness - or perhaps because of it - the show did not repeat the success of his earlier TV hits. In it, contestants were voted "babe" or "minger" depending on their attractiveness.
His other recent production, Five's Live With... talk show, has also been seen as being on the lame side, despite a change of host from Chris Moyles to Christian O'Connell.
Despite this, the mercurial former Tarzanogram is still famed for having made millions from his ability to capture the public's mood, a reputation built on his previous achievements.
Evans' return to Saturday nights comes nine years after the smash hit Don't Forget Your Toothbrush.
Evans' new show, Boys and Girls, has been criticised
He shot to fame in 1992, as host of The Big Breakfast, Channel 4's new early morning programme, having built his reputation as a witty prankster on the BBC's now-defunct London radio station GLR, where he started as a producer and ended up as a star DJ.
The Big Breakfast was a huge hit in the early days, beating even ITV's new breakfast station, GMTV, when it launched in 1993.
The Warrington-born star's hyperactive personality defined the show and he was catapulted from London cult personality to national celebrity.
He launched his own production outfit, Ginger Productions, responsible for Channel 4's Toothbrush, his first prime-time TV show.
The format was sold around the world, bringing in funds to help him build up his media empire.
He left the Big Breakfast in 1994, and the following year was recruited by BBC Radio 1 to revamp the station's breakfast show.
He bought Virgin Radio from Sir Richard Branson
However he took the job only on his proviso the show would be in the hands of Ginger Productions, not the BBC.
The deal ruffled feathers at Broadcasting House, but worked wonders for the station, which saw its ratings rocket, along with its profile.
In 1996 he returned again to Channel 4 screens with TFI Friday.
The show was a classic Evans cocktail of leading bands, celebrity chat, bizarre stunts and in-jokes.
But as TFI rose, his tempestuous love affair with the BBC was on the wane.
He quit Radio 1 in January 1997, after his demands to work a four-day week were refused.
Later that year he returned to breakfast radio, with Sir Richard Branson's Virgin station, competing against Radio 1's new breakfast line-up of Zoe Ball and Kevin Greening.
Evans liked the job so much, he bought Virgin Radio from Sir Richard at the end of 1997.
The City was stunned at his £85m purchase right from under the nose of London-based Capital Radio, whose bid to buy the station had been held up by a government inquiry.
He went to live in LA with wife Billie Piper
With City backers behind him, his new Ginger Media Group made him a broadcasting mogul.
But the Evans magic started to fade soon afterwards.
He was photographed out on the town with Paul Gascoigne - damaging the footballer's chances of getting into the England squad for the 1998 World Cup.
Ginger's TV arm showed signs of losing its flair. TFI Friday started to go off the boil, and two BBC projects, the National Lottery Red Alert and student quiz Carry on Campus, flopped.
But in early 2000 Evans was able to cash in on his success, selling the Ginger Media Group to SMG, the owner of ITV1 stations Scottish and Grampian, for £225m.
But while Evans took a large chunk of that cash, his on-air performances faltered.
A much-hyped "romance" with singer Geri Halliwell failed to lift TFI's ratings, and he stepped down as host before the show ended in 2000.
At Virgin, Evans failed to turn up for a week of breakfast shows and the station ignored his claim that he had been ill.
A string of TV failures has not deterred Evans
Photographs and footage had emerged of him out drinking with his new teenage girlfriend, Billie Piper, and Virgin said it had no option but to dismiss him.
Evans said the termination of his contract cost him £3m in lost share payouts, which arose from his sale of the company.
After marrying Piper in Las Vegas in May 2001, Evans kept an uncharacteristically low profile at his marital home in Hascombe, Surrey.
Soon the dream of year-round sunshine and an escape from the British media became too tempting and the couple moved to Los Angeles.
They celebrated their first anniversary - silencing critics who said the 17-year age gap between them and Evans' colourful past, would see the union fail.
In August last year Evans became embroiled in a tragedy when his friend James Ward - the former landlord of his village pub - fell overboard and drowned during a birthday sailing trip off the south coast.
Evans was said to have been deeply shocked by events.
The BBC's Nick Higham said of the High Court judgement: "This is personally damaging to him, Quite what it will do to him as a presenter of TV and radio programmes remains to be seen, but it can't be good news."