The filmmaker, Robin Hessman, 38, is an American who lived for long periods in Russia after college, and now splits her time between Brooklyn and Boston. She worked on “My Perestroika” for six years, shooting much of it herself and spending countless hours tracking down vintage footage and music. She said production costs were a bit more than $750,000.

Ms. Hessman said she had become fascinated by the generation of Russians now in their 40s, because they straddled two eras. “I wanted to show how complicated it is for a society, and how complicated it is for an individual, to make this transition,” she said. “The moments where we are in our lives, on these huge, sweeping waves of politics and history, affect us in ways that we can’t even begin to understand at the time that they are happening.”

Ms. Hessman’s timing may be fortunate, given how the uprisings in the Middle East seem to echo those that brought down Communism in the Soviet Union and its satellites. “My Perestroika” provides hints at what may await Egyptians who believe that with the old order toppled, they can expect radically positive changes.

Boris Meyerson, known by his nickname, Borya, and his wife, Lyubov, took to the ramparts in 1991 to defend Mikhail S. Gorbachev’s reforms against Soviet hardliners who sent tanks into the streets in an attempted coup. Now, Mr. Meyerson is so disgusted by the tightly controlled political system under Mr. Putin that he does not vote.