Frankie Ansell and his cousin Lee Ansell were sentenced to 45 months and 41 months, respectively. The third man, Howard Davey, was sentenced to 41 months in prison.
A fourth man, Joseph Plant, was given a 16 month suspended sentence and ordered to undertake 200 hours of unpaid work.
The group managed the pirate DVD business for two-and-a-half years, selling more than 31,000 copies worth more than £500,000.
The arrests came as part of an investigation by Suffolk Trading Standards and anti-piracy organisation the Federation Against Copyright Theft (FACT).
FACT notified Suffolk Trading Standards about Frankie Ansell, and a search of his home led to the recovery of £5,670 in cash, alongside 600 pirate DVDs.
Kieron Sharp, chief executive of FACT, said: “This was no one-man-band operation. This was a serious organised crime group who sold tens of thousands of DVDs pocketing more than £500,000 in criminal money.”
He added: “Many people think piracy is a victimless crime, however criminal operations like this have devastating effects on the creative industries and the people working in them. We would like to commend Suffolk Trading Standards for leading this investigation and will continue to work with trading standards and police forces across the country to crackdown on film/TV piracy.”