A pregnant woman was threatened with a screwdriver by an armed robber during a series of raids at shops and business premises.
Adam Wiechnicki also threatened a petrol station attendant with an axe and told another shop worker he had a gun.
The 28-year-old was locked up for five years and four months after a court heard how his crime spree had had a "devastating impact" on his victims.
Wiechnicki committed the offences during a nine-day "campaign of robbery" in Normanton, Wakefield and Feathertone.
Bashir Ahmed, prosecuting, told Leeds Crown Court how the offences were committed in January to fund the defendant's crack cocaine addiction.
Wiechnicki was carrying an axe in a plastic bag when he entered Prospect Garage, Castleford Road, Normanton, at 10.30am on January 4.
He approached the counter and asked a member of staff for a packet of cigarettes.
Wiechnicki then walked behind the counter and took the axe from the bag.
The member of staff managed to push the robber away and chased after him. He hurt his shin in the struggle.
In a victim statement, the man said: "It was the most frightening experience of my life. He was coming at me with an axe raised to my head."
Later the same day Wiechnicki threatened a woman at Castleford Road Off-Licence with an axe before taking £150 from the till.
On January 5 Wiechnicki left a pregnant shop worker terrified when he demanded money from a till as he brandished a screwdriver at Farm Foods, on Normanton High Street.
The woman believed the robber was holding a knife at the time. He managed to get away with £200.
Mr Ahmed said: "She did not want any risk to her unborn child and allowed him to reach over and grab as much money as he could."
The defendant kept apologising to the woman as he took the cash.
The victim said in her statement: "I would have described myself as a happy person and I enjoyed my work.
"But because of that man putting a knife under my chin I am unhappy in my work.
"I want the court to understand just what he did to me that day."
On January 10 he told a woman he was in possession of a gun when he tried to carry out a robbery at Premier Express, Girnhill Lane, Featherstone.
The shop worker refused to hand over any cash and he left with a packet of cigarettes without paying for them.
The victim later described how she was "petrified" and broke down in tears after the incident.
Wiechnicki, of no fixed address, pleaded guilty to three offences of robbery, two of attempted robbery, two of theft and four of possessing an offensive weapon.
Wiechnicki told police after his arrest that he committed the offences when he was "rattling" after taking crack cocaine.
He asked the court to take four further offences of burglary into account by the court.
Those offences included cash being grabbed from tills at commercial premises in Wakefield and Normanton.
Andrew Stranex, mitigating, said Wiechnicki was ashamed of what he had done.
He added that the defendant was seeking help for his drug addiction while in prison and was motivated to stay out of trouble in future.
Recorder Anthony Hawks told Wiechnicki: "You know the devastating impact that behaviour has had on the people you robbed."
As he was led from the dock, Wiechnicki said to a woman who was crying in the public gallery: "I'm sorry mum."
Wiechnicki was also made the subject of a criminal behaviour order.
The order bans him from entering 18 named business premises.
He must not remain in any retail premises in the Wakefield district if asked to leave by staff.
Wiechnicki must not enter or attempt to enter any driveway or garden in Wakefield without the occupier's permission.
He is also banned from entering commercial premises in Wakefield with any item of clothing covering his face.