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‘Failed politician struggling for relevance,’ Kevin O’Leary’s loud Oscars appearance has banded the internet together to roast him

O’Leary played business tycoon Milton Rockwell in Timothée Chalamet led ‘Marty Supreme.’

Kevin O’Leary wearing a black and silver patterned jacket at the Oscars, smiling with arms open, in front of a beige background with "OSCARS" signage.
O'Leary's NBA necklace is worth close to $30 million USD, making it one of the most expensive items ever worn on a red carpet (Courtesy: Instagram/drip)

What to know

  • Canadian Shark Tank investor Kevin O’Leary went to the Oscars in a gaudy silver and black outfit, which received countless comments from social media users roasting him.
  • His outfit’s focal point was a signed “triple logoman” NBA card on a Tiffany & Co. chain, worth close to $30 million USD.

Canadian businessman and Shark Tank personality Kevin O’Leary showed up to last night’s Oscars in an outfit so gaudy it hurts to look at.

He stepped onto the red carpet in a silver and black suit jacket, a waist sash, black pants, two Marty Supreme watches, and a signed “triple logoman” NBA card encased in a $30 million USD Tiffany & Co. chain. His necklace is one of the most expensive items ever worn on a red carpet.

Online reactions to O’Leary’s garish Oscars getup have not been kind. Social media users are calling him “embarrassing” and his outfit “hideous.” One X user writes, “Kevin O’Leary looks like he robbed the drapes from a luxury hotel lobby and called it fashion.” 

A Canadian X user made fun of O’Leary’s role in Marty Supreme, commenting, “As a Canadian, I’m proud of all the Canadian Oscar winners but I’m most proud that a movie with Kevin O’Leary in it lost all of its Oscar nominations.”

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His political failings and the fatal boating incident he was involved in also came under fire, with one person writing, “Kevin’s got zero cred. He’s nothing but a failed politician struggling for relevance and he should actually be in jail for manslaughter. #NeverTrustACon.” O’Leary vied for federal Conservative party leadership in 2017. 

People also pointed out the discrepancy between him and filmmaker Jafar Panahi, an Iranian filmmaker who could be facing prison upon his return to Iran, with one X user writing, “Two completely different worlds on the same red carpet: a millionaire flaunting his NBA cards worth $30 million in a Tiffany & Co. case made of white gold, diamonds, and rubies, next to an Iranian filmmaker who faces prison when he returns to Iran after the Oscars.”

Panahi’s film It Was Just an Accident about Iranian political prisoners was nominated for Best International Feature Film and Best Original Screenplay. 

O’Leary made his silver screen debut in Marty Supreme, the sports dramedy starring Timothée Chalamet about the American table tennis player Marty Reisman, where he played ruthless business tycoon Milton Rockwell.

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