In 1991, the Soviet Union finally crumbled under the weight of its own contradictions. As the walls came tumbling down, it looked as though a space was finally opening up for young people to express themselves after the crushing conformity of the communist years.

“For us it was awesome when the Soviet Union fell, because we could fool around,” says artist Illya Chichkan. “And that’s exactly what we did. We experimented with psychedelics and psychotropics. We tried everything.”

Rave promoter Artemy Troitsky was equally optimistic: “It looked like the people best equipped for the new times [were] us, the young people, who knew capitalist culture, who were dynamic and ready for cultural change.”

But things didn’t turn out quite as hoped. The brief window of opportunity that followed communism’s demise soon descended into the dangerous anarchy of unbounded capitalism. As for the stories of the cohort of Russians who attempted to articulate a new youth culture in those chaotic years, they’ve become the basis for director Clayton Vomero’s film 3OHA, which is about to receive its UK premiere at Sheffield Doc/Fest.

The first half of the film is dedicated to stories of what the 90s generation went through.

Troitsky, who became one of the nascent Russian club scene’s key figures, recalls organising the legendary Gagarin party in 1991: “I had been following the electronic scene in Riga, then Leningrad, then we brought the first rave to Moscow in December.”

Another organiser, Igor Shulinsky, pushed out into the world of publishing with Ptyuch magazine.

“We tried to do something like the Face magazine at the time,” he says in the film, acknowledging the fact that magazines such as NME, the Face and Melody Maker had been smuggled across borders during the 80s to feed a fervent hunger for another life. “We were like a bible for many people from all over the country. We did what we wanted, we had no taboos. We published everything we were interested in.”

But while some embraced the freedoms, which were being enacted against an increasingly violent and rackety background, others noticed that their understanding of the capitalism that was freeing them was sketchy at best.

Artist Vova Vorotnyov says: “Everyone was copying the west. They took the western stereotypes and the western mentality as they perceived them. And of course we’d been living behind the iron curtain so a lot of information was not reaching us.”

Increasing violence was also rendering much of the country ungovernable. As Vomero notes: “It was more dangerous in the 1990s than it had been in the 1980s. People lived through a broken and horrible state, and people like Shulinsky and Troitsky endured that and insulated themselves by creating clubs and magazines.”

There had been a period, Vomero says, when “there was a very short window of about two or three years where there was a moment of people being able to potentially build something, but the temptations of money and success were also great and so new that it was just two years that passed so quickly.”

Many of Troitsky’s generation “had a lot of regret for not having taken over ministries, of not having become the people that redid the train lines, did the things which would have had a long lasting effect politically and governmentally and institutionally.”

The second half of Vomero’s film fast-forwards to the present, and follows the current generation in Moscow, Kiev and St Petersburg, crushed by the repressions of Vladimir Putin’s modern gulag. The class of 1991 seem incredibly glamorous and with far more agency over their lives than their contemporary counterparts, whose narrow lives encompass illicit street meetings to hawk knock-off trainers on Moscow streets, or discussions of Crimean culture in dusty Kiev apartments. But Vomero’s lens treats the latter’s efforts to create ersatz visions of the west – dancing along to silent music videos in overgrown urban wildernesses while they capture themselves on Instagram – with sympathy.

And he captures the terrible pathos of a young couple discussing the possibility of a trip to Los Angeles – which is as likely as a trip to outer space – so poignantly that it has you choking back the tears. The current generation are left untethered at the end of the film, snapping selfies in front of western fashion outlets that remain as untouchable for them as they were for their forebears.

• 3OHA screens at Sheffield Doc/Fest on 8 and 11 June