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Oscars Outsider

Oscars Outsider

Written by: Oscars Outsider
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Oscars Outsider is a podcast where Craig Midwinter and Dylan Ferguson break down the Oscars the way most people break down sports. We follow the awards race week by week — the narratives, the precursors, the surprises, the discourse, and the strategy behind every contender’s campaign. We treat awards season like a competitive ecosystem, tracking momentum, analyzing the politics of voting bodies, and running our own Oscars Fantasy Draft to score nominations, wins, snubs, and everything in between. If you care about movies and the game behind the movies, you’re in the right place.Oscars Outsider Art
Episodes
  • Who Will Be the Villain of the 2027 Oscars?
    Oct 14 2026

    Craig and Dylan ask one of the juiciest questions of awards season: who is going to become this year’s Oscar villain?What actually makes a movie the villain of an awards race? We look back at some notorious examples — The Greatest Show on Earth, Crash, La La Land, and Green Book — and examine how politics, frontrunner fatigue, backlash, and the movie positioned as the “hero” can completely reshape an Oscar season.Then we turn to 2027. Could Fjord become the political lightning rod? Is I Play Rocky the kind of broad, backward-looking crowd-pleaser that awards watchers eventually turn on? Could Michael, Obsession, or even Toy Story 5 become the movie everyone is desperate to see lose?Plus: immediate changes to our Oscars Fantasy Draft, Artificial surging after New York, The Social Reckoning stumbling, Digger fading, and which films came out of NYFF looking stronger — or much weaker.Who do you think will be the villain of this awards season?#Oscars2027 #OscarsPredictions #AwardsSeason #OscarsOutsider

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    56 mins
  • Will Digger even get drafted? It's our 2027 Oscars Fantasy Draft!
    Oct 6 2026

    It's DRAFT DAY on Oscars Outsider!


    Craig and Dylan go head-to-head in our second annual Oscars Fantasy Draft, selecting 26 films they think will dominate the 2027 Academy Awards and the awards season leading up to them.


    With *The Odyssey* looking like the obvious first overall pick, is there any strategy that can beat Christopher Nolan's epic? And how much should we be willing to gamble on films like *Dune: Part Three*, *Project Hail Mary*, and *I Play Rocky*?


    Plus, we dig into the disastrous opening of *Digger*, debate whether Tom Cruise still has a shot at an Oscar nomination, and discuss what the Warner Bros. shake-up could mean for the future of ambitious studio filmmaking.


    There are risky picks, an actual draft-day trade, some immediate regrets, and a few movies we might already be betting against.


    **Follow the draft all season long:** https://oscarsoutsider.com


    Who has the stronger roster? What did we draft way too early? And which movie did we foolishly leave on the board?


    Let us know in the comments!


    #Oscars2027 #OscarsPredictions #TheOdyssey #Dune3 #OscarsOutsider

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    1 hr and 29 mins
  • Oscar News, NYFF Buzz & Best Documentary Predictions
    Sep 29 2026

    The Oscar race keeps getting messier. We break down the first reactions to Digger, the New York Film Festival relaunch of Paper Tiger, the growing momentum behind I Play Rocky, and the latest category-placement news around The Odyssey. Then we dive into what may be the most controversial Oscar category: Best Documentary.

    We make our early documentary predictions and get into NAZA, Musk, 14th, You Can See Everything, The History of Concrete, Once Upon a Time in Harlem and more — plus the bizarre history of a category where Academy voters once reportedly used flashlights to signal when they wanted a movie eliminated.

    And before we wrap up, we preview next week’s Oscars Outsider fantasy draft and some of the rule changes we’re making for year two.

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    59 mins
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