Trump\'s Most Awkward Interview From 2003 Leaked
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Love him or hate him, this 2003 Ali G (Sacha Baron Cohen) interview with Donald Trump is a bizarre classic pic.twitter.com/DSfu117Brv
— Time Capsule Tales (@timecaptales) December 18, 2025
Love him or hate him, this 2003 interview between Ali G—the outrageous persona created by Sacha Baron Cohen—and Donald Trump is a genuinely bizarre time capsule. What starts as a seemingly playful chat quickly turns into an awkward, fascinating clash of styles, with Ali G’s absurd questions meeting Trump’s deadpan confidence. The result is an unintentionally hilarious exchange that still circulates today as a cult-classic moment, showing just how strange—and oddly revealing—early 2000s pop culture interviews could be.