Is one of Cinema’s biggest breakout stars in 2025, a 71-year-old Canadian entrepreneur? Yes, you read right. Kevin O’Leary has come out of nowhere to surprise us all with a fantastic performance in buzzy Oscar contender MARTY SUPREME, as businessman Milton Rockwell! The Dragons’ Den and Shark Tank star makes a very natural transition to the big screen in Josh Safdie‘s latest, with a key role as husband to Gwyneth Paltrow‘s Kay Stone, while also seeing a lucrative business opportunity in Timothée Chalamet’s titular character.
O’Leary has been doing the rounds this week in support of the Christmas Day release, spotted a couple times already at new Yorkville hotspot, Powder Room, where he was spotted enjoying an intimate Nick Jonas performance.
We finally met O’Leary, who was so kind to stop for a snap before completing his rounds. A gentleman!
@mrwillwong Watch Shark Tank and Dragon’s Den king KEVIN O’LEARY transform into an Actor in buzzy #MartySupreme, in theatres 12.25.25. #kevinoleary #dreambig ♬ Forever Young – Alphaville
(Photo/video credit: Mr. Will Wong)
For advertising opportunites please contact mrwill@mrwillwong.com