It was one of those surreal moments when light entertainment mugs history. Vladimir Putin crooned the song Blueberry Hill at a children’s charity benefit in St Petersburg in 2010, as a crowd of celebrities – including Sharon Stone, Kevin Costner, Kurt Russell, Goldie Hawn, Gérard Depardieu, Vincent Cassel and Monica Bellucci – clapped along like they were in kindergarten. When the politician reeled off the opening line – “I found my thrill” – thoughts of the Georgian invasion or the poisoning of Alexander Litvinenko didn’t seem to be urgently popping into anyone’s head. Knowing what we know now, the spectacle plays more like Dr Evil’s rendition of Just the Two of Us – but far less funny. In 2022, after Putin’s ruthless assault on Ukraine, the guests present that day must feel very naive, perhaps even ashamed – but they are not the only western celebs who cosied up to Putin. In defence of this bunch, they had been booked to appear by Samuel Aroutiounian, a New Yorker who specialised in bringing Hollywood talent to Russia and later said that he had been unaware Putin would be appearing.

Now, as big names from Angelina Jolie to Sean Penn and Mark Ruffalo issue their support for besieged Ukraine, Hollywood must be cringing at the days when a public appearance with Putin wasn’t beyond the pale. In the mid-2000s, he had merely nibbled at a few former Soviet provinces and seen off the odd dissident – events that didn’t trouble most Entertainment Weekly readers. Russia was an important emerging film market, and firmly on the celebrity junket circuit. So Jean-Claude Van Damme, in 2007, could happily buff the president’s macho credentials at a St Petersburg MMA event, while Leonardo DiCaprio purred at his fellow feline lover during a big-cat conservation summit in 2010.

His hegemony firmly established by then, Putin already had a domestic entertainment machine working hard in his favour. Channel One – descendant of the Soviet-era state TV station RTO – had produced Night Watch and Day Watch, two aspiring global blockbusters that put a manichaean gloss on the chaotic post-communist Russia that Putin had quelled in the early 21st century. “Dark means freedom and light means responsibility – and, in real life, Putin, for sure, is a light one,” said director Timur Bekmambetov at the time. “He is trying to fix everything, make everything organised. But it’s very bad for freedom.” Perhaps the succession of jingoistic military films the Russian cinema industry was also starting to churn out – which included 2005’s 9th Company, 2008’s Admiral and 2013’s Stalingrad – were a true bellwether of his actual allegiance.

But Putin – lambasted for his aggressions in Chechnya and Georgia, and with suspicions swirling around state agencies after the killings of Litvinenko and Anna Politkovskaya – was sorely in need of international legitimacy. Photo ops with big stars and the implied entry into the VIP area of global mass entertainment helped normalise his rogue state in the eyes of the world.

Or so he assumed. By 2014, when Putin had annexed Crimea and by which time it was obvious he wasn’t going to surrender the leadership any time soon, Hollywood was starting to run shy. Talking to Time magazine, Blueberry Hill mastermind Aroutiounian said of the A-list: “They’re much more concerned about not killing their careers. [In the current political climate] they don’t know what will happen to them when they come back home. They will take a lot of heat.” With his inscrutable air, machiavellian geopolitical schemes and his critics’ habit of dying in outlandish assassinations, Putin was increasingly resembling a cartoonish arch-villain of the Blofeld ilk. His foreign military intelligence agency was even called GRU, like the Despicable Me baddie. But there remained a coterie of film-world refuseniks who were unbothered by his growing pariah status: not just Depardieu, but Mickey Rourke, Steven Seagal and director Oliver Stone. In fact, this set of leathery iconoclasts and libertarians seemed to actively embrace it.

Three of them fell into the useful-idiot camp. Depardieu took Russian citizenship, and its refreshing 13 per cent flat tax rate, in 2013, after criticising the French government over its levying plans. On friendly terms with Putin, he called Russia “a great democracy” in an open letter. At a Latvian film festival in 2014, Depardieu was sufficiently high on great sentiments to declare Ukraine “part of Russia”. Cue tanks rolling across the border in 2022 and the sound of tarte à l’humble being scoffed: “I am against this fratricidal war,” he said. “I say, ‘Stop the weapons and negotiate.’”

Maybe that’s what the Moscow celebrity train has helped obscure all along – for Putin, it has always really been about a colder, harsher reality

Rourke, meanwhile, was unfazed by Putin’s Crimea incursion and judged him “a real gentleman” while buying a T-shirt with the leader’s face on it at a Moscow department store in 2014. “I met him a couple of times and he was a very cool regular guy, looked me right in the eye,” he told Sky News. It’s easy to assume this was some kind of edgelord publicity stunt from the one-time hellraiser, but he offered up his Russian girlfriend as the real reason: “It’s all about family. I don’t give a f**k about the politics. That’s not my department.”

Seagal doesn’t even try to play that get-out-of-jail-free card. Granted Russian citizenship in 2016, he had already called Putin’s Crimea annexation “very reasonable” and lauded the president as “one of the world’s greatest living leaders”. With his old pal now trashing the rest of Ukraine, he’s only dialled down his support one notch:

“I look at Russia and Ukraine as one family and really believe it is an outside entity spending huge sums of money on propaganda to provoke the two countries to be at odds with each other,” he told Fox News.

You can see why – in a kind of Botoxed 21st-century version of the Hollywood Ten – three over-the-hill blowhard actors might identify and want to shack up with the Russian president. Stone’s case is more complicated. He had already made documentaries about Fidel Castro and Hugo Chávez, so with his past proclivity for revolutionary figureheads, Putin was a logical next candidate. The director’s four-hour 2017 series, The Putin Interviews, undoubtedly indulges the leader but in doing so it draws him out in all his bland cynicism. It also picks its moments to challenge him: on Chechnya, on Russian “democracy”, on election interference.

It’s not hard to understand what Stone got out of discussing realpolitik with his country’s adversary. The bigger question is how Putin benefited from this arrangement. Could the series, in continually insisting on the equivalence between US and Russian expansionism, have been part of his broader disinformation strategy? To throw a tantalising bone to sympathetic liberal anti-imperialists to distract them from his real endeavour during the period: radicalising the US and Europe’s nativist right wing.

At least Stone’s dalliance with Putin gave us an opportunity to sit and watch the surface of the man – even if it didn’t quite get at what lay beyond. In one remarkable vignette, the director gets the autocrat to sit for his first viewing of Dr Strangelove. As the climactic mushroom-cloud montage plays out, Putin seems faintly amused by this depiction of mutually assured destruction: “Nothing has changed.” Maybe that’s what the Moscow celebrity train has helped obscure all along – for Putin, it has always really been about a colder, harsher reality. – Guardian