34 Movies Like Sideways (2004)

An action movie on struggling with failure late in life, featuring a once-in-a-lifetime performance by Mickey Rourke .

Peter Dinklage's bittersweet masterpiece on getting out of loneliness.

A startling yet realistic gangster drama with the always amazing Viggo Mortensen .

If this visually breath-taking and heart-wrenching film doesn't make you cry, nothing will. .

Up until an unexpected twist, James Gandolfini's second-to-last movie is a sweet and charming comedy about dating after divorce. .

Adam Sandler, though currently imminently marketable, incredibly played out and boring, used to be a real actor. This is the film by which his legacy will be judged, where we see the funnyman drop the mask and actually show real feelings besides bumbling rage. Sandler's hurt and confused performance is beautifully vulnerable and true and is complimented by P.T. Anderson's incomparable direction (the man behind Boogie Nights and There Will Be Blood), creating a true masterpiece of American cinema. This beauty also stars Philip Seymour Hoffman and Emily Watson.

Will Ferrell plays a well organized IRS agent named Harold Crick who seems to have figured out everything in his life to the dot. Little does he know his life is being run by someone else, a nervous and morbid novelist, famous for ending her works with the death of the main character. As the nature of his life and eventual doom, he decides to lay back and enjoy the ride, breaking all his ingrained and boring habits. While this film is recommended for everyone, Will Ferrel fans, especially, need to watch this to see Will's acting variety.

The self destructive, substance abusing history teacher Dan (Ryan Gosling) works in a Brooklyn middle-school and is constantly at odds with the curriculum, preferring to teach 13 year old kids Marxist theory in class. Meanwhile, his student Drey (Shareeka Epps) has to go through struggles of her own, her brother being in jail on drug charges and her single mother having to work long hours to make ends meet. Slowly, an unlikely and tender friendship between teacher and student evolves, in which it becomes less and less clear who of them is the adult part. Steering away from cliches, Half Neslon is not your typical social drama. Its intelligent plot twists, great cast (with outstanding performances by both Gossling and Epps) and slow, non dramatic storytelling makes this a highly underestimated movie that, although treating depressive topics without any easy relief for the viewer, will leave with an inner smile, albeit a sad one.

In this comedy/drama, Bill Murray plays an aged, dispirited war veteran named Vincent who openly disdains most people and gives little attention to anything beyond alcohol and horse racing. Living a life of solitude in Brooklyn, everything takes a turn when a young single mother (Melissa McCarthy) and her son Oliver move in next door. Vincent eventually takes on the responsibility of watching over Oliver when Maggie is at work. Murray is perfectly unpleasant in his darkly comedic role, as his relationship with Oliver evolves despite his own misgivings, providing young Oliver (Jaeden Lieberher) with the fatherly/grandfatherly presence he desperately needs. Though somewhat formulaic, St. Vincent rises above expectations by way of great dialogue, favourable performances from all of the leads, and an unbelievably touching finale that will melt your heart. Much better than you probably expect—definitely check this one out.