Alexander Payne has yet to make a bad movie and his 2004 classic is one of his best, a buddy road comedy about the struggles of moving forward. The juxtaposition between Jack’s impending marriage (and erstwhile affair) and Miles’ almost romance with a woman they meet in wine country shows how hard it is to let yourself be happy, when making a huge mistake is so easy. Jack probably will never learn his lesson, but there’s still hope for Miles. Its bittersweet ending leaves us on a cliffhanger, right before the final moment of redemption. Sideways is just about perfect.
22. Silver Linings’ Playbook
David O. Russell has always been a talented singular voice in cinema, but Silver Linings’ Playbook was his most mature and accomplished feature yet. This screwball romantic dramedy recalled both Preston Sturges and Robert Altman, filled with sharp overlapping dialogue and great characters. The always wonderful Jennifer Lawrence rightly nabbed an Oscar for her work here, as an anti-Manic Pixie Dream Girl too smart to be a stereotype. Lawrence has her own problems and agendas, and if you’re lucky, you just might deserve a girl like her.
23. There’s Something About Mary
The Farrelly Brothers have yet to top their 1998 sleeper hit, a gross-out comedy remembered for its infamous hair gel scene. But what’s most memorable about There’s Something About Mary isn’t its toilet humor but it’s strangely affecting sentimentality. This movie is bursting with genuine heart and real romance, proving that there’s nothing a guy wouldn’t do to be with Cameron Diaz, America’s then dream girlfriend. Even Brett Favre couldn’t resist her charms.
24. The Upside of Anger
The Upside of Anger is like Pride and Prejudice if it were about Mrs. Bennett, except Mrs. Bennett is now an irascible matriarch played by Joan Allen. After her husband vanishes, Allen struggles with the responsibilities of maintaining a family while dealing with her own fraught emotions, as unresolved frustrations bubble to the surface. This is a movie about relationships and women that presents life as it is, complicated, emotional and often unlikeable. In a film culture where we rarely let women be complex, this movie is a necessary antidote.
25. Vicky Cristina Barcelona
Late in his career, Woody Allen has become increasingly sensual as a filmmaker, and his 2008 ode to Catalonia finds him in the mood for frolicking, if not love. Vicky Cristina Barcelona is about how we present the world as a set of ideals, rather than looking at life in its natural state, and how those principles hold us back. Both Vicky and Cristina have their diametrically opposed views on life, yet neither win them fulfillment. They might not find themselves in the Catalonian countryside, but hopefully they end the tumultuous summer a little wiser about love.