George Michael's chequered history with motor vehicles finally caught up with him this week when, as punishment for crashing his Range Rover into a branch of Snappy Snaps while stoned, he was handed down the ultimate humiliation – an open letter from Tony Parsons in the Mirror saying he couldn't handle his spliffs. To make matters worse, he was also sentenced on Tuesday to eight weeks in Pentonville prison, of which he will spend four in custody and four "on licence" in the community. Still, those worried as to how Michael will cope in the clink can at least take comfort in the fact that he's far from the first musician to spend time inside; the list includes Sid Vicious, Chuck Berry, Rick James, Paul McCartney and, most recently, Happy Mondays' Bez.

Perhaps the most famous musical lag of recent times is Pete Doherty. His first spell inside (sentenced to six months in 2003 for burgling Libertines bandmate Carl Barât) was a time of creative inspiration. As well as a prison journal and a scrapbook of doodles, Doherty wrote the song Pentonville, which complained about the perils of sleeping on a "lumpy mattress" (the sound of an outpouring of public sympathy was noticeably absent from the mix). "Prison is a horror story," he told the Evening Standard in 2006. "The inmates terrified me. You know, I've never harmed anybody else except myself, but some of those guys . . . "

James Brown served jail terms before and after his fame, but like Doherty, his first – aged 16 for armed robbery – would be the most productive. It was while serving time that Brown's vocal talent caught the ears of Bobby Byrd. Byrd was so blown away that he helped Brown secure early release, and the pair went on to work together in the Famous Flames. The Rolling Stones also feature famous jailbirds – although Mick Jagger and Keith Richards only spent a single night in the cells in 1967 for drugs charges as they were released on bail the next day pending appeal. While awaiting the hearings the band recorded We Love You, the video for which recreated the 1895 trial of Oscar Wilde. The writer is a good reference point for arty types behind bars (Doherty often namechecked him), as his time in Reading Gaol defines the image of a creative outlaw who has been punished unfairly.

There is, of course, only so much moaning the casual fan will tolerate, and while time inside is undoubtedly horrible, you'd be best advised to take it with dignity and a dash of humour. Contrast Phil Spector's letters from inside – which complained about being surrounded by lowlife scumbags who would "kill you for a 39-cent bag of soup" – with, say, Boy George's post-prison Glastonbury performance, during which he sang Nobody Knows the Trouble I've Seen and cheekily changed the words of Karma Chameleon to "I'm a man, with three convictions." In PR terms, avoiding self-pity is crucial.

Dead pigeons stuffed with weed

One cliche is for pop stars to "find God" while in jail. Love's Arthur Lee even told the Guardian in 2002 that God had instructed him to reform his band, the Lord Almighty apparently a big fan of Forever Changes. There may be other benefits, too – Ian Brown converted to Islam while serving time in Strangeways because it was the only way to ensure he received chicken dinners: "After all," Brown whispered darkly, "you never did know what was in them meat pies." The former Stone Roses frontman emerged armed with great anecdotes, including one tale of dead pigeons stuffed with "an ounce of weed" sailing over the prison walls and into the gym yard.

Despite rock'n'roll's sketchy past, if we really want to get genre specific then the world of hip-hop is where you'll see the most sentences served. Despite claims that jail time can be good for credibility (Lil' Kim's 2005 spell in jail was regarded in more cynical quarters as a PR coup, for instance), the reality is that most rappers find it hard to maintain a career from behind bars. The importance of not fading away has not been lost on Lil' Wayne. Since being sentenced to a year in Rikers Island prison for gun possession in March, he's managed to start a blog (which publishes his letters from jail), sell Free Weezy T-shirts from his website and work on an album with Drake – contributing tracks that he recorded over the prison telephone, no less. Posting on his Weezy Thanx You blog, Wayne provided an insight into a typical day at Rikers: "I wake up around 11am, have some coffee. Call my kids, and my wonderful mother. I then shower up. Read fan mail. Have lunch. Back on the phone. Read a book or write some thoughts down. Have dinner. Phone. Pushups. Then I listen to ESPN on the radio. Read the Bible, then sleep. That's my day."

Another rapper who maintained their career trajectory from within a cell was Tupac Shakur, who became the first artist to have an American No 1 while in jail with his album Me Against the World. Tupac also found time in jail to get married, write a screenplay (Live 2 Tell) and read, among other things, Sun Tzu's The Art of War. Alarmingly for George Michael, however, might be the fact that Tupac described withdrawal from weed as one of the most startling aspects of starting his prison term. Still, given that so many musicians have faced time inside before and come out relatively unscathed, perhaps the singer shouldn't worry too much. It's only eight weeks, after all, and if he can just keep his head down, start a blog, write a new album, find God, find another god and read several tomes on Chinese military strategy then he should be OK.

Erwin James: 'Prison could restore George's sense of reality'



Take it from me: Pentonville is one of London's less salubrious prisons. Waking up in this grimy, ancient prison – famed as the main holding jail for the city's drunks, drug abusers and down-and-outs – will be George Michael's all-time low.

I was there three decades ago, during my own derelict days. Our landing – the boozers' landing – was lice-infested and stinking. We, in our ill-fitting shirts and ragged jeans, were the lowest of the low. In fairness, things have changed, but not dramatically. Only four years ago, the then prisons inspector, Anne Owers, said the prison was "overrun with cockroaches and vermin" and that many prisoners lived in fear; sometimes, they lacked pillows and food.

But Pentonville's most famous prisoner may benefit from some improvements, such as the substance misuse unit, which offers "harm minimisation and health promotion modules". The bad news is that, like most UK prisons, Pentonville is awash with drugs.

He will need to be strong, but early indications are that his strength has deserted him: a man who shared a cell with him at the courthouse described how he sat "crying his eyes out". No shame in that. He won't be the first grown man to burst into tears at the sound of cell door banging shut – nor the last. But once he has got over his initial terror, he might recognise this as an opportunity.

Emotionally, the pressures that come with wealth and stardom can be just as debilitating as poverty and strife. Alone in a cell, he will have time to reflect and hopefully heal. Prison can and does break people, but it can make them, too. Michael has been in the spotlight for decades, but there must still be occasions when, even to him, his sense of reality seems distorted. Prison could restore it.

Famous people often become targets for bullies on a prison landing, but he's a global star who has given pleasure to millions and caused serious harm only to himself. I think he will be safe. He might be asked to sing, though: maybe a tongue-in-cheek request for Outside.

And the excitement generated by his presence will lift the morale of everyone there, prisoners and guards alike. Seeing the former Wham! singer queueing for porridge in the morning would be unforgettable.