Olivia Wilde – This Had Oscar Buzz

Happy New Year, Garys! We’re kicking off 2026 with something more bubbly and light-hearted, 2019’s Booksmart. Sold as an ultra-modern and female take on boy-led high school raunch comedies, the film stars Kaitlyn Dever and Beanie Feldstein as best friends who decide to live it up after spending their entire high school experience stuck in books. After debuting at SXSW, the film generated a mountain of discussion that yielded disappointing box office results, but managed to stick around in the precursor race until the last minute.

This episode, we talk about the film’s delightful ensemble of faces of the future and Olivia Wilde’s debut directing duties that earned her a number of first film prizes that season. We also talk about Feldstein’s drubbing during the Funny Girl run on Broadway, Dever joins our Six Timers Club, and the shadow of Lady Bird unfairly set expectations for this film.

Topics also include Forte vs. Arnett, the 2019 Globe Musical/Comedy Best Actress nominees, and “I wish you luck with your trees.”

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We don’t know if we’re equipped to episode this much, but here we are. A bomb so fiery, we brought host of The Incinerator podcast host Billy Ray Brewton to help us unpack it all: 2018′s Life Itself. From This Is Us’ Dan Fogelman, the film assembles a large ensemble including Oscar Isaac, Olivia Wilde, Olivia Cooke, and Antonio Banderas to tell a tale of big emotions, intergenerational heartache, and unreliable narrators. The film arrived as a TIFF gala with big weepy expectations, and like a rogue MTA bus right out of the film, critics brought on a brutal and well-earned drubbing.

After partnering with other distributors for previous releases, this film was Amazon’s widest solo release and quickly became as big of a bomb for audiences as it was for critics. This episode, we unpack what makes it such a mess and how Amazon succeeded that year with Cold War instead. We also talk about the umpteen versions of “Make You Feel My Love,” This is Us’ Emmy flub this season, and Amazon’s purchase of United Artists.

Topics also include Annette Bening “I don’t know her”-ing Natalie Portman, Deuxmoi culture, and the Grammys of Soy Bomb and “Sonny Came Home”.

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Tag: Olivia Wilde

374 – Booksmart

207 – Life Itself (with Billy Ray Brewton)