5. I Love You, Man
Paul Rudd and Jason Segel star in this unrelentingly funny bro-mantic comedy, directed by John Hamburg. Rudd plays Peter Klaven, a real estate agent who has just gotten engaged and is troubled by his lack of male friends. He has no qualified best man contenders and at the urging of his fiancee Zoe (Rashida Jones) decides to shop around for a new best friend. At one of his open houses, he meets Sydney Fife, a free-spirited investor who frequents house showings to pick up divorcees and enjoy the free catering. Despite being near opposites, Peter and Sydney hit it off almost immediately, and quickly become so close that Peter and Zoe's relationship soon seems at risk. This is really just a terrific lighthearted comedy, with countless quotable jokes ("Slappa da bass, mon!"), likable characters (Is there a more affable star out there than Paul Rudd?) , and perfect chemistry between the actors. There isn't a whole lot to dissect or analyze; it's just a wonderfully enjoyable romp that I find myself able to watch just about anytime. Also on a personal level I Love You, Man is largely responsible for my newfound appreciation for the music of Rush.
4. Up in the Air
Adapted from the 2001 novel of the same name, Wunderkind director Jason Reitman's third film stars George Clooney as Ryan Bingham, a professional downsizer. Ryan's company gets hired out by other companies going through layoffs, to travel to their site and fire their employees for them. Ryan prides himself on being a lifelong bachelor with little to no roots anywhere in the country, and also on "making limbo tolerable" for his clients' unfortunate victims. Two events throw Ryan's simple, easily manageable life into turmoil: he meets and begins to fall for fellow business traveler Alex (Vera Farmiga) who initially seems to be the female version of him; and his firm decides to cut costs by pulling all their agents off the road and moving to a virtual business model, firing people via videoconference. This revolutionary new strategy is introduced by Natalie (Anna Kendrick), a new hire fresh out of college with designs on reshaping the industry. During the transition, Natalie is sent on the road with Ryan to get acclimated with the business, and her tendency to question Ryan's life choices forces him reexamine his own mindset. Clooney is wonderful as always, projecting his usual swagger mixed with a world-weary loneliness that belies his outward demeanor. Kendrick injects her character with a cocksure energy but reveals great vulnerability as Natalie realizes the severity of what her job entails. The script manages to pull countless upliftingly comedic moments out of what seems to be a depressing backdrop - the comatose state of The American Dream. 2009 was a year of brutally difficult economic times, and Up in the Air is a perfect reflection of what we as a nation were going through.