Commencement season is upon us once more, and around the country important people are getting paid hundreds of thousands of dollars to grace the Class of ‘08 with some measured words that will be forgotten almost immediately. But what happens when the graduation caps float back down to earth, the booze finally wears off, and you find yourself sitting in your childhood bedroom thinking, “Um, okay. What happens now?” At that point, it’s time to watch some MOVIES. If you’re already lining up your Netflix queue for a marathon post-graduation R&R session, be sure to throw a couple of these into the mix. Some are inspirational, while others serve more as cautionary tales. All of them will fill in some of the gaps that your commencement speaker left out: The Graduate (1967)
This is the ultimate graduation movie based on its name alone. And even though it came out ages ago, it tackles a timeless post-college conundrum: How do you find sex beyond the carnal conveniences of the dorm? Benjamin Braddock (Dustin Hoffman) discovers his answer in the form of pop culture’s most famous cougars (Anne Bancroft as Mrs. Robinson), but at what price? I guess the invaluable lesson of The Graduate is even if you’re feeling a little lost and disillusioned after college, you shouldn’t fornicate willy-nilly with older people. Because when you’ve got a generation gap staring you in the face, that’s tantamount to sleeping with the enemy. Reality Bites (1994)
This film paved the way for the web-to-TV series Quarterlife, but thankfully it is much funnier and does not involve “vlogging.” Lelaina Pierce (Winona Ryder) graduates college, settles in Houston, and starts filming a mockumentary about life as twentysomethings. Her cast? Friends Troy (a wannabe musician; Ethan Hawke), Vicki (a Gap manager who thinks she might have AIDs; Janeane Garfofalo), and Sammy (a bloke struggling with his sexuality; Steve Zahn). When Lelaina meets a TV exec/interest who promises to get her film onto the air (Ben Stiller), she must choose between chilling with yuppies and keeping it real with grungy nihilists. Since keeping it real is essentially the greatest challenge of post-college life, this plot is pretty on point. St. Elmo's Fire (1985)
Emilio Estevez, Rob Lowe, and Demi Moore? Yeah, people, we're talking about the 80s…deal with it! Named after an extreme weather phenomenon, St. Elmo’s Fire takes a broad stroke to the challenges of the post-college transition, presenting seven central characters who are all struggling in their own unique ways. Billy is a recovering frat boy who can’t hold down a job. Kevin’s a depressed writer stuck scribing obits while trying to figure out LIFE in his free time. Wendy’s a rich virgin, so you know she’s got some issues to sort through. Anyway, you get the general idea. There’s a nice smorgasbord of lost souls, so you should be able to find at least one character you relate to. (Trivia: Estevez was also in The Breakfast Club playing a high school student in the same year that St. Elmo’s came out…talk about versatility!). Into the Wild (2007)
Whoa, depressing! Yeah, I feel you—this film is mad depressing. But watch it for two reasons: 1) Hal Holbrook is amazing and will make you cry. 2) It teaches the important lesson that there really is such a thing as “reading too many books.” Post-grad life is all about balance—by obsessively reading Thoreau and hanging out by himself, Chris McCandless (Emile Hirsch) is extremely imbalanced (perhaps chemically so). While we can all agree that “selling out” and being materialistic are definitely two slippery slopes to avoid, hauling ass to the literally slippery slopes of Alaska might not be the best alternative. Lost in Translation (2003)
Traveling after graduation is a time-honored tradition, and it can be a lot of fun when done right. But tagging along to Tokyo with your new husband whom you secretly resent? That’s just a bit depressing. While sitting around a hotel staring blankly at things, Charlotte (Scarlett Johansson) crosses paths with Bob Harris (Bill Murray), an aging movie star who no longer feels the magic. One is entering adulthood and feeling lost; the other is preparing for old age and feeling lost. Hopefully the “in-between” part is sort of fun? One thing that’s important to remember about this film is that Charlotte is a Yale graduate with a philosophy degree. It would be weird if she weren’t depressed. The Nanny Diaries (2007)
Talk about being typecast! Scar-Jo has the “aimless recent grad/aspiring professional” role on lockdown. (See also: Scoop.) Here, she plays Annie Braddock, an NYU grad who finds herself in a situation familiar to many twentysomethings in Manhattan—i.e., broke with no real job prospects. After questioning her desire to go into finance, she pimps out her babysitting services to a wealthy New York family. Surprise, surprise, the job is horrible, but luckily there’s a prince charming on the Upper East Side ready to save Annie from her torture. Lesson learned: not every first job is a good one. But if you’re a nanny, at least you can write a best-selling book about it, as did Emma McLaughlin and Nicola Kraus, authors of the novel that inspired the film. Kicking and Screaming (1995)
Not the one with Will Ferrell, which came out a decade later, but rather a cautionary tale that makes two very important points: 1) Sticking around campus post-graduation is invariably depressing, and 2) If you break up with a someone who achieves even marginal success after school, it will quickly eat away at any façade of happiness that you attempt to foster. Point #2 is even more apropos in the Facebook era, when you can track your exes' every move while you sit in your squalid sublet apartment crying. But one thing is true in any era: cracking jokes about how you’re unemployed and unmotivated is fun for a while, but it’s not a sustainable existence in the long run. (I guess that’s point #3.) The Motorcycle Diaries (2004)
What better way to celebrate the end of college than by figuring out who that dude was that everyone had a poster of in their dorm room? As a medical student in 1950s Argentina, Ché Guevara (Gael García Bernal) gets on a motorcycle and embarks on an epic trip across South America with his college buddy. Along the way, they get into some typical 23-year-old shenanigans—chasing tail, drinking beers, and hitchhiking. But then Ché flips the script and becomes one of the most famous revolutionaries of all time. This flick is a must for any young grad with counter-cultural aspirations or a passing interest in the lives of people outside of the United States. The Devil Wears Prada (2006)
Bosses from hell, soul-crushing assistant-level jobs, and rocky transitions to a new city—DWP really covers the major challenges of the post-college transition in one fell swoop. Andy Sachs (Anne Hathaway) moves to New York City to pursue her dreams of being a fashion journalist. There, she becomes the assistant to Miranda Priestley (a/k/a Anna Wintour; played by Meryl Streep), who runs the leading fashion rag Runway (a/k/a Vogue). Like The Nanny Diaries, this story comes from a roman à clef written by ex-assistant Lauren Weisberger. So, if you want to be a successful author, work for rich people in New York and then expose them. It’s a foolproof formula. Definitely, Maybe (2008)
In his Van Wilder days, Ryan Reynolds was scared to leave college—the real world was looking like a pretty big pond and he just wanted his days as campus kingpin to last forever. But in this “instant classic” rom-com, he plays Will, a Wisconsin grad who travels to (where else?) New York City with a suitcase full of ambition and naiveté. He’s thinking about how he’s going to marry his college sweetheart while simultaneously repping Bill Clinton like his life depends on it. It’s a portentous path seeing as infidelity becomes the central theme the movie. With his life tracing the rough timeline of the mobile phone boom, Will finds himself in some pretty dark places, haunted by phrases like “being realistic” and “growing up.” But in the end it’s all good, because he has the ultimate trump card in post-college life: a cute daughter (Little Miss Sunshine’s Abigail Breslin).

Honorable Mentions

Euro Trip (2004)
These jokers may have just graduated high school, but a European boondoggle is a classic post-college maneuver. Euro Trip is also a criminally underrated movie, thanks in part to this song. Cougar Club (2007)
I haven’t even seen this movie, but it looks so incredible that I’m putting it on the list anyway. “Spence” and “Hogan” are two recent grads working for divorce lawyers. They form the Cougar Club, a secret society of young men devoted to hamboning older women—The Graduate meets American Pie. Back of the net! Beer Fest (2006)
Sometimes you need to relapse into “college mode” by playing loads of drinking games and acting incredibly irresponsibly. Let this be your inspiration. Herbie Fully Loaded (2005)
Imagine getting a talking car for your graduation gift? That would be the jam.

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Movie poster images from The Internet Movie Database (IMDB).