Robert Murphy, 67, was told by a sheriff his problem was that he "just simply didn't care".
Sheriff Craig McSherry told him his catalogue of previous convictions was "the worst record I have ever seen".
Murphy, of Dunfermline, pleaded guilty at Dunfermline Sheriff Court to driving his motorcycle on Keirs Brae, Cardenden, Fife, on June 3 while banned from the roads.
He also admitted having no insurance.
The court heard he had racked up three dozen convictions for driving while disqualified.
Murphy's lawyer Alisdair Macleod said: "Mr Murphy is perfectly aware that it may be the only option for the court to send him to custody.
"However, in respect of his circumstances and also responsibilities towards his wife who has recently had an operation in hospital - which was the catalyst to this offence - he is a man of an age where realistically sending him to jail will result in him being released in four months time."
He said reports showed Murphy had "attended very well" to the requirements of the three-year community payback order imposed for his last conviction.
Sheriff McSherry jailed Murphy for eight months.
He said: "This is the 36th offence and time you have driven while disqualified.
"Not only have you shown complete contempt for the court, but you are also putting others' safety at risk. You just simply don't care."