From Leonardo DiCaprio to Steven Seagal, Tinseltown’s biggest names were once happy to hang out with the invading president. Are they all now cringing? Not entirely

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-00s, 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.

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