5 Movies Like Wonder Boys (2000)

Movies to watch after Wonder Boys (2000).

Enough Said is a realistically sweet movie that handles serious emotions without compromising its comedic chops. It portrays the difficulties and doubts that come with post-divorce relations in a somewhat goofy and original way. James Gandolfini is impeccably wonderful in his last lead role, and joined by Julia Louis-Dreyfus they generate exquisite chemistry right from their first scene together all the way until the movie ends. Like many other beautiful movies such as Your Sister’s Sister, Enough Said is hilarious, romantic, but to that it adds being smart and realistic. You'll love it.

Robert Downey Jr., Channing Tatum, and Shia LaBeouf star in this powerful drama about growing up in 80's Astoria, New York. It follows the memoirs of the author, director and musician Dito Montiel as he visits his ailing father after 15 years in Los Angeles, away from home. Told via flashback and present-day exposition, as well as several fourth-wall bending monologues,  A Guide to Recognizing Your Saints is a coming of age film that leaves a deep impact, with two Sundance awards and heaps of nominations to its credit. 

Starring Matthew Broderick and a young Reese Witherspoon as, respectively, Jim McAllister, a high school teacher and Tracy Flick, a notorious 'that girl' in his class. When Tracy decides to run for class president, we see the floodgates open as all sorts of bizarre and insane behavior pours out of the two. Quickly, it becomes clear that Tracy will do nearly anything to win, and as circumstances spiral out of control, madness descends - along with hilarity!

Set during the swingin' seventies, two small town Connecticut families are the subject of this visually stunning and somewhat disturbing drama. With an all-star cast that includes Sigourney Weaver as Janey Carver, an unsatisfied housewife and mother of two and Elijah Wood as her eldest son, there's plenty of star power and drama. In addition, director Ang Lee brings his signature sense of trial and unease while unleashing a quirky and pointed 70's aesthetic.

With an ensemble cast featuring a young Natalie Portman and a less murderous Uma Thurman, Ted Demme's "Beautiful Girls" recreates the worries and woes that thrive in the minds of a tight knit group of working class friends stuck in their own small town Massachusetts world. Warm, quirky and filled with champagne diamonds, both metaphorical and tangible, for anybody who's ever walked the thirty something walk, it's a film that'll make you want to remember all the friends you wish you still had and actually still do.

Also see: The Very Best
The Very Best are our staff picks, they're all rated 8.0 and above. Here, we selected a few for you.
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