He posed for photos in Lower Manhattan on Sunday alongside fans and his dead ringers – some dressed as the 28-year-old’s characters from the Wonka and Dune movies.
But just as the wannabe-Chalamets began competing along a red carpet in New York’s Washington Square Park, police ordered the group to disperse.
Organisers were hit with a $500 (£385) fine for an “unpermitted costume contest” and at least one person was taken away in handcuffs.
The group reassembled in a nearby playground, where more than a dozen contestants vied for audience approval from a makeshift stage.
After whittling the group down to the last four, the remaining participants were then tested on various topics.
They were asked about their French proficiency, their plans to make the world a better place and their romantic intentions with Kylie Jenner. Chalamet and Jenner are said to be a couple.
Eventually, Miles Mitchell, 21, from Staten Island was picked as the winner, taking home $50 (£38) in prize money which appeared in the form of a novelty-size cheque written out to the “Best Tim”.
He was dressed in a purple Willy Wonka outfit and tossed candy to the crowd from a briefcase.
“I’m excited and I’m also overwhelmed,” Mitchell said. “There were so many good look-alikes.”
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Commenting on the chaos of the event and the arrest, organiser Paige Nguyen said: “It started off as a silly joke and now it’s turned pandemonium.”
A spokesperson for the NYPD said charges were pending.