Kevin O’Leary proved he doesn’t just play a rich show-off on TV—he’s also a rich show-off in real-life—on the 2026 Oscars red carpet on Sunday night.
O’Leary, who has a supporting role in Josh Safdie’s Oscar-nominated film, Marty Supreme, took the red carpet in a black suit embellished with silver depictions of what looks like Ancient Greek art. He completed the look with a cloth belt tied in the front, and his framed Michael Jordan-Kobe Bryant basketball card necklace. This is not the first time he’s busted out this necklace—he also wore it to the Actor Awards earlier this month. Page Six reports the bling, which O’Leary had customized at Tiffany’s, is worth a jaw-dropping $19.2 million.
Not everyone was impressed by O’Leary flaunting is wealth. In an objectively hilarious red carpet clip posted online by Vanity Fair, acclaimed Iranian filmmaker Jafar Pahani—who’s heartbreaking film It Was Just an Accident is up for Best International Feature—looked on in bewilderment as O’Leary lifted his tricked-out basketball card to his mouth.
It was truly a brutal, but very well-earned side-eyed. That clip, and O’Leary’s outfit, quickly became the first viral moment of the night, with social media users comparing O’Leary’s look to “the wallpaper in an overpriced Italian restaurant’s bathroom.”
O’Leary, best known as the bald guy on Shark Tank, made his feature film debut last year in Marty Supreme, where he plays a wealthy businessman who takes an interest in tennis table champion Marty Mauser (Timothée Chalamet). Most notably, there’s a scene in Marty Supreme where O’Leary spanks Chalamet’s bare bottom.
Sorry O’Leary, we’re out on this one. Better luck next time to Mr. Wonderful.
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