One might have thought, having served four months in prison this year, that Boy George would have had enough of being incarcerated with a bunch of undesirables.

Instead, the singer will tomorrow become the first person to go to court to fight for the right to be locked up inside the Big Brother house, after his probation officers sought to block him taking up a lucrative offer to appear on the programme next month.

The high court will judge tomorrow morning whether the nation should be sentenced to up to three weeks of uninterrupted footage of the 48-year-old former drug addict, alongside other inmates rumoured to include Pamela Anderson, MC Hammer and the Hollywood madam Heidi Fleiss.

Fleiss also has some experience of captivity, having served 21 months for tax evasion in the late 1990s.

Channel 4 have confirmed the musician, whose real name is George O’Dowd, has been invited to appear on the final series of Celebrity Big Brother, which starts on 3 January, reportedly for a fee of £200,000. But as O’Dowd is on licence after a conviction for falsely imprisoning a male escort in April 2007, the probation service has refused his request.

O’Dowd has been free on licence since May this year, after serving part of a 15-month sentence for handcuffing a Norwegian man to a wall in his east London home. He was initially given strict curfew conditions and wore an electronic tag, though he no longer does so.

The programme’s producers are understood to have offered to accommodate his special circumstances, such as permitting him to be visited in the house by his probation officer, but London Probation declined his request.

The service declined to comment in detail, but is expected to argue in court that permitting O’Dowd to appear would undermine confidence in the judicial service; it is also thought to have concerns on behalf of his victim.

The former Culture Club singer was also fined and sentenced to community service in New York in 2006 for falsely reporting a burglary.