Ruhen Miah, 42, of Newbury, Berkshire, used his job as a licensed taxi driver to attack four women who were trying to get home after nights out in Newbury town centre.
Judge Angela Morris, sentencing at Reading Crown Court, told Miah that some of the victims were "so intoxicated they had no chance of defending themselves".
Morris said there was "a degree of targeting" in Miah's behaviour and he had abused the trust not just of his victims but also friends who had put them in his taxi and urged him to get them home safely.
Miah was sentenced to 14 years imprisonment for rape, five years for assault by penetration, eight years for an attempted rape and 18 months each for two counts of sexual assault.
He had previously pleaded guilty to all counts. The sentences are to be served concurrently.
The women, including three who were 19 and another who was 29, were attacked between January 1 and February 24.
Two of the January assaults were within 90 minutes of each other.
At one point Miah stopped a male friend of one of his victims from getting into his taxi.
He raped another woman in his friend's empty council flat, the court heard.
DNA evidence matched Miah to the crimes and dashcam footage helped place the victims.
Bangladesh-born Miah, who had no previous convictions, is married with three children.
The court heard he had described himself as a pillar of the community and had run a restaurant that closed in September 2017.
Prosecutor Alan Blake said the rape victim recalled "he kept repeating to her 'in my country, we are very respectful of women'."
Mr Blake said: "Her next memory is him driving her back to the road where she lived and told her that she did not have to pay."
She went to bed and later reported the rape to hospital staff.
She pointed out that her life is very different now as she is not able to sleep, and suffers anxiety and depression.
Another distraught victim now describes herself as "damaged goods" adding "this will have a huge impact on my life and being able to trust".
Michael Wolkind QC, defending, said Miah had "remorse and horror over what he did" and described him as a "good man who went wrong for a number of reasons".
This included his business failing and his relationship with his wife going wrong.
In a similar case in 2009 taxi driver John Worboys was convicted of 19 sex offences, but was believed to have committed many more.
Some of his victims recently spoke out against his bid for parole.
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