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25 Best Comedy Movies on Amazon Prime Video Right Now

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ITALY – OCTOBER 19: George Clooney at the movie ‘Up in the Air’ Premiere in Rome, Italy on October 19, 2009. (Photo by Eric VANDEVILLE/Gamma-Rapho via Getty Images)
ITALY – OCTOBER 19: George Clooney at the movie ‘Up in the Air’ Premiere in Rome, Italy on October 19, 2009. (Photo by Eric VANDEVILLE/Gamma-Rapho via Getty Images) /

9. Up in the Air

Release Year: 2009

Written By: Jason Reitman and Sheldon Turner

Directed By: Jason Reitman

Starring: George Clooney, Vera Farmiga, Anna Kendrick, Danny McBride

Much like other films featured on this list, Up in the Air isn’t a laugh-out-loud hilarious comedy like most moviegoers are accustomed to. But the second entry in director Jason Reitman’s unbeatable trio of bitingly funny films about flawed characters is as light and airy as it title suggests.

Just as Juno’s Juno MacGuff unpacks the implications of young love and teenage pregnancy and Young Adult’s Mavis Gary navigates the murky waters of the post-high school plummet, Up in the Air’s Ryan Bingham (George Clooney) searches for stability. Although his frequent flyer miles and unattached attitude suggest differently, Ryan meets two women, Natalie (Anna Kendrick) and Alex (Vera Farmiga), who alter his flight path.

Up in the Air became a critical darling, earning six Academy Award nominations—including Best Picture, Best Director, Best Adapted Screenplay, Best Actor, and individual Best Supporting Actress nods for Vera Farmiga and Anna Kendrick. For a poignant yet playful look into the lens of the executive world, Up in the Air is just the ticket.