Inside Diddy's Two Oscar Wins

There’s no denying that Diddy is hip-hop royalty. In addition to his successful career as a producer and mogul, he can now add two-time Oscar winner to his profile. Diddy recently shared he took home his second gold trophy during the 2021 Academy Awards. The first was for a 2011 documentary he served as a producer on.

Diddy is a producer on the 2012 Oscar-winning documentary ‘Undefeated’

Undefeated chronicles the struggles of The Manassas Tigers,  a Memphis high school football team who embark on a comeback following years of losses. The team is turned around by coach Bill Courtney. Courtney not only focuses on the team’s athleticism – but also transitions them into academic scholars.

The film was released in select theaters March 2011 and was well received by critics. 

Diddy happily attended the 2012 84th annual Academy Awards alongside the directors of Undefeated in anticipation of a win for the documentary film. While walking the red carpet, he spoke highly of being part of the project.

Related: Andre Harrell Fired Diddy From Uptown Records to Teach Him a Lesson

“I’m one of the producers on the film and I’m just a part of the team,” Diddy said during one interview. “Tonight really belongs to these guys and I’m here as part of their entourage and here to make sure you guys go out and see the movie.”

When speaking to TODAY about the Oscar-win, Diddy couldn’t contain his excitement. As for why the documentary resonates so much with viewers, Diddy says it’s due to the emotional aspect of the film.

“It’s really like a human drama piece about these three kids lives and the life of this coach who really believes in these kids and then they started to believe in themselves and he gives these incredible speeches and by the end of the movie, one of the most trouble youths on the team – he gives a speech that’s one of those Bill types of speeches that breaks you down into tears,” Diddy said.

The hip hop mogul won his second Oscar for 2020 short film ‘Two Distant Strangers’

Undefeated wouldn’t be the only film Diddy would lend his name to. He serves as a producer on Two Distant Strangers, a 2020 American short science-fiction drama that examines the deaths of Black Americans during encounters with police. The encounters are through the eyes of a character trapped in a time loop that continuously ends in his death.

Two Distant Strangers was distributed by Netflix amid the COVID-19 pandemic, becoming available for streaming in April 2021. The original film’s release was in November 2020.

Related: Why Diddy Blasted The Grammy Awards

Following the announcement of the film’s win, Diddy shared a joyous video of his live reaction on Instagram. In the video, he jumps for joy and hugs his mom in excitement.

“I’m incredibly blessed to WIN MY SECOND OSCAR as a producer for UNDEFEATED and now @2distantstrangers,” Diddy captioned the video. Words can’t describe how I feel right now winning alongside my brothers…WE DID IT!!!”

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