5) Michael Douglas – 23 Years
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Wall Street’s Gordon Gekko, with his yuppie sensibilities and dated fashion sense, was such a product of the 1980s that it was a strange idea to resurrect him nearly two and a half decades later. But that’s exactly what director Oliver Stone did, with Michael Douglas back in one of his best known roles.
2010’s Wall Street: Money Never Sleeps was flawed, but it had a good premise at the heart of it – how would the real-life financial recession affect Gekko? – and Douglas easily slipped back into the role. It also co-starred Shia LaBeouf, back when he was the king of resurrecting 80s properties after featuring in Transformers and Indiana Jones and the Kingdom of the Crystal Skull.