Anna Kendrick stars opposite of George Clooney in this dramedy about a corporate downsizer named Ryan (Clooney) who spent 322 out the last 365 days on a plane — not as a pilot or crew member, but as a someone who's flown in by companies to lay off employees. He's essentially the middle man who delivers the bad news, and Natalie (Kendrick), a new hire, has a plan that could ultimately be the death of Ryan's career. Determined to save his job, Ryan brings her along so she can physically see the gravity of face-to-face meetings. In the middle of all this, Ryan's also trying to juggle his casual relationship with a fellow frequent flier. Unlike most films on this list, this one you can actually enjoy stress-free in the sky.