The actor was presenting the Video of the Year award, which went to Swift's song "You Need to Calm Down".
However, in an apparent case of mistaken identity, he tried to hand the Moon Man trophy to Jolie, who looked confused but shook off the moment and gave the actor a hug.
Fans pointed out that Jolie is known for her uncanny impression of the 29-year-old and was wearing a very similar hair style to Swift's on the night.
"John Travolta mistaking Jade Jolie for Taylor Swift. DRAG RACE EXCELLENCE," one viewer tweeted.
Travolta's mishap comes five years after he notoriously announced Idina Menzel's name at the 2014 Ocsars as "Adele Dazeem".
He blamed the incident on Goldie Hawn, whom he claimed was distracting him from a production assistant trying to explain Menzel's name would be spelled phoenetically on the teleprompter.
The cast of Swift's video did in fact get their own trophies. The pop star reportedly told the VMAs in advance that she not perform live unless each of the cast members in her "You Need to Calm Down" video received their own Moon Man statue with their name on it.
The VMAs took place on Monday night (26 August) in New Jersey, where the winners included Swift, Lil Nas X, Shawn Mendes and Camila Cabello, and Missy Elliot.
See the full list of winners here.
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