Robbers wearing balaclavas threatened to douse a night porter in petrol in a terrifying hotel raid.
Brett Riddell, 32, and James Regan, 40, had travelled from Birmingham to carry out the "stupid, ill thought through" robbery at The Judges Hotel near Yarm.
The pair forced their way into the luxury venue at 3:10 in the morning.
Riddell, who is pictured smirking in his mug shot, had worked there in 2002 while an inmate at Kirklevington Prison and returned uninvited on November 28 last year.
But a "comical" attempt to get the safe open saw them leave with just bottles of spirits from the bar, a small amount of cash and a mobile phone Teesside Crown Court heard.
Prosecutor Harry Hadfield said the night porter had heard the bell go, but initially ignored it.
When it rang again he suspected a guest must have forgotten their keys.
The court heard how the pair were carrying a can of petrol and chillingly warned the victim not to scream or they would douse him in it.
The ordeal would go on to last more than one hour.
One of the men pretended to talk into an earpiece, claiming more 'gang-members' were outside as he set about locating the safe - and demanded the keys to it.
When the victim told them the keys were kept off site, they began snatching tools from a shed outside in a failed attempt to break into it.
Riddell and Regan ultimately grabbed a bin from the kitchen and filled it with £2,660 worth of spirits, before stealing the victim's phone and wallet.
The pair then fled in their getaway car, at around 4.15am, in an attempt to head straight back to the Midlands.
But they didn't get far.
The man alerted the police and the Skoda was stopped on the A1 near Wetherby around one hour later - the stolen items and two balaclavas were found inside.
In interview, Riddell explained how the duo had met in rehab.
A victim statement said the complainant had to leave his job four days after the incident and had only been able to source part time work since.
He had been prescribed depression and anxiety medication, had trouble sleeping and his friends have noticed a difference in him.
The statement added: "My life has completely been affected."
Regan had no previous convictions, but his accomplice Riddell had a long rap sheet, with 32 convictions for 85 offences.
They included robbery, assault on a constable, racially aggravated common assault and possession of a blade.
Susan Hirst, mitigating for Riddell, said the crime "wasn't a properly planned robbery" and done on the "spur of the moment".
Sam Faulks, for Regan, said his client had shown remorse and had never been convicted in the past.
He said that the prosecution's suggestion that the distance travelled made it professionally planned was "a nonsense".
The pair were sentenced for robbery and having an offensive weapon.
Speaking of the weapon, Judge Peter Armstrong said:
Riddell, of Waterslack Road, Doncaster, was jailed for six years, Regan, of Hawfield Grove, Birmingham, for three years.