Shameless Jamie Forbes, 38, added six further offences to his previous list of 296 crimes - admitting burglary, shop theft and breaches of previous court orders.
Grimsby Crown Court heard that after being stopped by a security guard at an Asda he boasted: "I can get a grand a week out of you lot."
Sentencing Forbes to 21 months in jail, Recorder Simon Jackson QC said: "You are one of the most persistent offenders that has appeared recently at this court."
Prosecutor Claire Holmes told the court how Forbes went into the Asda superstore in Holles Street, Grimsby, on May 21, breaching a previous antisocial behaviour order imposed in 2014 for three years.
He was immediately recognised by a security guard named in court as Mr Sutcliffe.
But the guard was distracted and Forbes wandered into the aisles and was later spotted leaving the store with his jacket bulging. He was found with £50 worth of stolen DVDs.
The next day police were alerted when Forbes smashed the lower pane of glass in the locked door of M&S in Victoria Street at 9.45pm.
He squeezed through the gap in the door and stole seven bottles of spirits valued at £119.
The damage to the door was estimated at £160. Police attended but Forbes had fled the scene.
The thief returned to Asda on May 25 just before 3pm when he stole six jars of Nescafe and six coffee refill packs valued at £76.
He was stopped at the door by staff.
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He returned to Asda at 9pm on Friday, May 27, and was stopped in the store by a security guard and bragged: "I can get a grand a week out of you lot."
Miss Holmes said there was no corroboration of his claim but "it reflected his attitude".
She said on May 31 he was apprehended trying to leave the B&M store in Kennedy Way, Immingham, North East Lincs.,
He was arrested for that offence and tested positive for cocaine.
The court heard he was subject to a community order for previous offences at the time of his latest spree.
Richard Hackfath, defending Forbes, of South Killingholme, North East Lincs., said: "This man's life has been ruined by drugs. It goes back to 1992. He has had a drug problem throughout his adult life.
"He has never been able to come to terms with it and has been in a vicious cycle of offending to support a drug addiction."
He added his client stole because he was "hungry and homeless and addicted to drugs".