Up in the Air (2009)

While this film has a strange concept, just watch it, you won't be disappointed.
Ryan Bingham (George Clooney) flies around the country, firing people from companies who are consolidated. He loves flying, loves hotels and airport bars. Basically, he's an asshole. He doesn't do long-term relationships and his contact with his sisters is almost non-existent.
But times are changing. Technology is about what he loves most obsolete. Enter Natalie Keener (Anna Kendrick), she is a brilliant young mind from Cornell and has the great idea to fire people virtually a concept Ryan loathes. So now, he has a partner in the air, something that he's never had before.
Natalie is a young idealist, thinking that she can have it all, the ideal marriage and excel at her career, but she's naive and even when her boyfriend dumps her via text (no shame, I dumped the only guy I've ever dumped via text), she declares that she could have made that relationship work, truer love there's never been. However, while Natalie came up with this idea, she's not like Ryan, she thrives on companionship and has a heart and real feelings, feelings that Ryan refuses to acknowledge.
While Natalie plays a pivotal role in Ryan's life, so does Alex (Vera Farmiga). Alex's job is not really described but basically she's the female version of Ryan, flying across the country constantly. They start a casual, no strings attached sort of relationship and Ryan's fine with that, until he flies back to his hometown for his younger sister's (Melanie Lynskey's) wedding when he starts to realize that maybe he wants something more, even though just weeks ago, he claimed that that was the last thing he wanted. Too bad it won't be with Alex. Alex, as it turns out, in one of the most shocking scenes captured on film in the last decade, is married and has a family, though you would have never guessed it based on her inspiring speech to Natalie.
While the film ends in what would have been a happy ending for Ryan at the start of the film, he's been on a journey and is left hollower than he was before, proving that you're allowed to change your mind. It's a shame that getting everything you've ever wanted doesn't come with the happy ending you always anticipated.
Despite the ending that, as the title suggests, is up in the air, the journey is a brilliant one, with aerial shots of the various cities Ryan travels to, interlaced with reactions to those he fired, the film is a quite masterpiece. The acting is top-notch and all three of the main actors earned fully deserved Oscar nominations, though sadly none of them would win. And the scenery is brilliant, with a realistic feel to it, but most importantly, this film forces you to think as all great movies should do and you'll remember it long after the credits have rolled. Grade: A
Side Notes:
-The supporting cast is brilliant, with Jason Bateman, Chris Lowell, Sam Elliott, Danny McBride, Amy Morton and J.K. Simmons.
-This film is also proof that ever the most casual mention of suicide should be taken seriously.
-Ryan finally thinks of his family toward the end, transferring some of his many miles to his sister and her new groom.
-For the record, the other times I was dumped, one guy did it over the phone and the other guy did it in person.
-You should never quit a job via text.
-I don't blame Natalie for bringing her pillow with her, I bring my pillow with me wherever I go.
-Also, for the record, I hate flying and honestly, traveling in general.
-While you die alone, hopefully won't have to journey alone.