Young adulthood has long represented a rich source of inspiration for moviemakers. This confusing and confused life stage offers moviemakers ample room for gross-out comedy, tender drama, tragedy and everything in between.

Many classic movies have explored the theme of a young character’s coming of age, from Great Expectations to The Graduate. It is clear why moviemakers have continually panned for cinematic gold by exploring their young characters’ winding path to adulthood: The psychic terrain is so wonderfully rich and complicated, the emotional stakes are so high.

Joining the ranks of the coming-of-age genre is The Way, Way Back, the feature directing debut of Oscar-winning duo Nat Faxon and Jim Rash, who, last year, won the Best Adapted Screenplay Academy Award for The Descendants. The movie centers on Duncan (Liam James, The Killing), an introverted 14-year-old, who, over the course of summer vacation, comes into his own, thanks to the unexpected friendship he strikes up with Owen (Sam Rockwell), the gregarious manager of the local water park. The much-older Owen becomes a mentor for Duncan, helping him open up (including with the girl he has a crush on, played by AnnaSophia Robb) and ensuring that this will be one summer Duncan will never forget. The great cast also includes Steve Carell, Toni Collette, Amanda Peet, Allison Janney, Rob Corddry and Maya Rudolph.

The Way, Way Back, which premiered to an enthusiastic reception earlier this year at the Sundance Film Festival, is currently in limited release. In recognition of this always fascinating genre, join MM as we take a look back at some of the best coming-of-age movies of the last 30 years.

    • Breaking Away (1979) | directed by Peter Yates                                                                                                                                                                                       

The oldest movie on our list may also be the most heartwarming. A classic of the coming-of-age genre, Breaking Away revolves around a small-town teen (Dennis Christopher) obsessed with Italian bicycling and vying for the attention of an older college girl (Robyn Douglass). Along with his townie friends (wonderfully played by pre-stars Dennis Quaid, Jackie Earle Haley and Daniel Stern), he enters a competitive bike race that could change his life. The movie takes place during the summer after high school graduation, as each of the four friends must come to terms with life after high school. Paul Dooley and Barbara Barrie have memorable, hilarious supporting turns as Christopher’s well-meaning but clueless parents. The movie manages to be both hysterically funny and surprisingly touching as it charts these teens’ struggles to “break away” from their small town lives.

      • Rushmore (1998) | directed by Wes Anderson

Rushmore deals with the unlikely friendship between two men, one younger and one much older. Jason Schwartzman plays Max Fischer, a sophomore at prestigious prep school Rushmore Academy. While Max holds a position in every extracurricular club imaginable (including the play director and bee hive keeper), his grades are terrible and he is promptly expelled from school. It isn’t long before Max and his middle-aged steel tycoon friend, Herman Blume (Bill Murray), both fall in love with Miss Cross (Olivia Williams), the first grade teacher at Rushmore whom Max helps out after school. Max and Blume soon engage in a hilarious battle as they vie for the attention and love of Miss Cross. While Max and Blume vary drastically in age, they are both basically little boys on the inside. Schwartzman is perfect as the smart and cunning Max, while Murray gives one of the best performances of his career as the grumpy, world-weary Mr. Blume, who comes to care for Max more than he does his own sons, and who sees in Max aspects of his own young, ambitious self.

      • Wonder Boys (2000) | directed by Curtis Hanson

Based on Michael Chabon’s acclaimed novel, Wonder Boys follows Grady Tripp (Michael Douglas), English professor/has-been writer/stoner, as he struggles to get his life together during one crazy weekend. The “coming-of-age” character in the film is James Leer (Tobey Maguire), an odd, quirky loner who is one of Grady’s students and happens to be an exceptional writer. Over the weekend, Grady and James form a close relationship; it’s obvious Grady sees his younger self in “wonder boy” James. Featuring a superb supporting cast (including Frances McDormand, Robert Downey Jr., Rip Torn and Katie Holmes), Wonder Boys is yet another movie on our list that deals with the unique bond between a world-weary older character and a confused youngster who is sorely in need of direction. If you haven’t seen it, be sure to check out this underrated classic—which also features a great Bob Dylan tune (“Things Have Changed”) written expressly for the movie.

      • Ghost World (2001) | directed by Terry Zwigoff

Adapted from the much-loved graphic novel by Daniel Clowes (who co-wrote the script with director Zwigoff), Ghost World perfectly captures the confusion and aimlessness of the recent high school graduate. The movie centers on Enid (Thora Birch), a quirky 18-year-old who’s just graduated from high school. Enid’s sarcastic humor masks the fear that she has no idea what to do with her life. She spends most of her time making fun of and mentally torturing people with her best friend, Rebecca (Scarlett Johansson). When they zero in on oddball 40ish loner, Seymour (Steve Buscemi), looking for Miss Right and obsessed with collecting old blues records, the girls’ friendship begins to dissolve as Enid’s relationship with Seymour begins to blossom. At times funny, sad and touching, Ghost World is a great little movie which features a fine lead performance by Birch (American Beauty) as the reliably deadpan and hilarious Enid, who hates the commercialized, synthetic world around her (hence the title). The ubiquitous Buscemi is also perfect as the music-obsessed loner who finds a kindred spirit in Enid. From uproarious beginning to thought-provoking, ambiguous end, Ghost World shows what true friendship is all about and wonderfully captures the confusion and aimlessness many teenagers feel after graduating high school.

      • The Squid and the Whale (2005) | directed by Noah Baumbach

This painful, unflinching, semi-autobiographical tale (based on director Baumbach’s own experiences) concerns the divorce of two married writers (Jeff Daniels and Laura Linney) and the devastating effect this has on their two sons, teenager Walt (Jesse Eisenberg) and younger brother Frank (Owen Kline). Walt idolizes his college professor father, a has-been writer who looks down on everyone as not being up to his intellectual standards (“philistines” as he calls them) and fancies himself an expert on every possible subject. Frank, meanwhile, prefers his mother, who is on the verge of achieving great success, having just gotten a major book deal. When Bernard and Joan announce their separation, the battle lines are drawn as Walt and Frank are forced to choose sides. What follows is surprising and revealing, as both boys come to terms with their relationships to their parents, and by the end, Walt finally sees that his father—whom he once idolized—as the extremely flawed, even pathetic, man he is. Daniels delivers the performance of his career as the overbearing yet all-too-human father the boys must learn to leave behind.

      • Adventureland (2009) | directed by Greg Mottola

This bittersweet tale follows James (Eisenberg again, who after this movie and The Squid and the Whale, has the market locked on playing aimless young intellectuals), a recent college grad who lands an awful job for the summer—working at the uber-cheesy amusement park of the title. The perks, however, include meeting the tantalizing Em (Kristen Stewart), with whom James quickly falls in love. Helmed by underrated moviemaker Greg Mottola (Superbad, The Daytrippers) and featuring an excellent soundtrack of classic ’80s tunes (including The Cure, Lou Reed and David Bowie), Adventureland didn’t really get a fair shake during its theatrical release, when it was mis-marketed as a run-of-the-mill teen comedy. The movie, however, shares more in common with Cameron Crowe’s heartfelt dramedies than it does American Pie. Adventureland is a small gem that deftly balances the sophomoric hijinx of your typical teen comedy with some detailed and realistic observations about being a young adult working in a crummy job, waiting for one’s real life to start.

Have a fave coming-of-age classic that didn’t make the cut? Let us know in the comments!