Everyone knew this was going to be on the list from the second they read the headline, so let’s get it over with, shall we? Dustin Hoffman deals with post-college ennui and the generation gap in mid-century Los Angeles, and takes the moving walkway at LAX in the most imitated tracking shot of all time (see: Mad Men Season 7 premiere). A defining film of the late-’60s/early-’70s New Hollywood canon, The Graduate gave the world “Mrs. Robinson” and a legendary closing shot.
The Bell Jar
Another obvious pick, but Plath did early-20s despair way before it was cool. The poet’s only novel, it’s the somewhat-autobiographical story of a young woman who moves to New York, takes an internship at a prestigious publication, and suffers a nervous breakdown. That may sound cliché now, but back in the early ’60s, it was a groundbreaking account of a woman’s struggles with mental health, preceding even Betty Friedan’s “problem that has no name” by a few months. A stereotypical high school touchstone, but worth reading once you’re closer to protagonist Esther Greenwood’s age.
Jessica Abel’s mid-’90s comic series deals principally “with young Chicagoans grappling with serious questions in their lives, such as Does she love me?, Can I stay friends with someone who has betrayed my trust?, and Can I make a life as an artist?” Post-grad social probz in a nutshell, and beautifully illustrated to boot.
Before there was Girls, there was Lena Dunham’s micro-budget feature film, currently available for streaming on Netflix. Like Girls, it stars Dunham, and like Girls, it features Dunham’s IRL friend Jemimah Kirke and IRL mom Laurie Simmons. Protagonist Aura has graduated from liberal arts college and moved back in with her successful artist parents while she figures out how a film studies degree translates into an actual creative career. There’s also sibling rivalry and awkward relationships with dudes. It may not be relatable for those of us without a TriBeCa loft to crash in, but it’s a fascinating look at Dunham pre-HBO.
On a much lighter note, the story of Elle Woods’ transition from sorority life to Harvard Law student — without sacrificing an ounce of her fabulously femme aesthetic in the process — is downright inspiring. Reese Witherspoon’s Elle sticks it to her condescending ex and wins a case based on her knowledge of perms. We’ll ignore the sequel and stick with the go-to girl power flick we’ve loved for the 13 years (!!!) it’s existed in the world.
The Mysteries of Pittsburgh
Right up there with White Teeth in the this-was-partially-written-while-the-author-was-still-an-undergrad?! hall of fame, Michael Chabon’s debut novel follows Art Bechstein during the summer following his graduation from the University of Pittsburgh (which is also, predictably, Chabon’s alma mater). Bechstein deals with the looming shadow of his Mafia-involved dad and his possible bisexuality. Also, there was a quickly forgotten movie version with Sienna Miller as Art’s love interest, Phlox Lombardi.
Its most recent claim to fame is that it inspired Candace Bushnell to write the book that eventually became Sex and the City, but it goes without saying that this Mary McCarthy novel is so much more than that. Published in the early ’60s, it’s the story of the relationships between four Vassar graduates in the ’30s. Marriage happens, as does divorce, death, and grad school. The Group also has the distinction of being the second work on this list to get a Mad Men shoutout (Season 3, Episode 10).
The ’90s cult classic turned 20 mere months ago, but the Ben Stiller-directed story of Gen X malaise in Houston, Texas still hits close to home. Winona Ryder is Lelaina, an aspiring documentarian; Ethan Hawke is Troy, her friend and roommate, with whom she has a truckload of sexual tension; and Ben Stiller is Michael, the new boyfriend who lands Lelaina’s documentary on a major network. A thinly disguised MTV and an HIV scare ground Reality Bites in its historical era, though the struggling-artist-makes-professional-compromises story is a timeless one.
Beating out Noah Baumbach’s earlier Kicking and Screaming by a hair, last summer’s black-and-white stunner spends a lot of time feeling like an episode of Girls and ends up being what A.O. Scott aptly calls “a bedtime story for anxious millennials.” Greta Gerwig’s Frances deals with the dissolution of college friendships and the realization that she’s growing a little too old for underemployment to be cute. But as she makes her way through various New York apartments and a weekend jaunt to Paris, she eventually lands on her feet. The implication is that Baumbach’s target audience probably will, too.
My Misspent Youth
This collection’s title essay, which ran in the New Yorker in 1999, lays out author Meghan Daum’s financial downward spiral as what happened when Daum’s romanticized vision of New York 20-something life met the realities of paying hand over fist for grad school and rent. Other reflections on turn-of-the-21st-century young womanhood include a reflection on an online romance, a diatribe against carpeted floors, and a meditation on Daum’s response to the untimely death of a friend. The result is one of the better takes in recent memory on a genre that has plenty of mileage: the personal essayist taking stock of city life.
Ilana Glazer and Abbi Jacobson’s freshman comedy, adapted from their popular web series, hit a nerve with legions of fans for all kinds of reasons: the series shows women smoking pot like the NBD it is; there are guest stars and UCB cameos all over the place; and, of course, it’s flat-out hilarious. Writing for The Guardian, Ann Friedman nails why Broad City strikes such a chord with slacker ladies who haven’t quite figured it out yet: “In the past few years we’ve seen more shows and movies featuring female fuckups… But usually, these women are embarrassed by their failure to get it together, and their insecurities spill over to poison their friendships and romantic relationships alike. By contrast, the women of Broad City exhibit very real imperfections without the self-loathing.” ABBI + ILANA FOREVER.
St. Elmo’s Fire
The Brat Pack (including Rob Lowe) hangs around DC after graduating from Georgetown. It’s no Breakfast Club, but it does feature half the detention crew, plus Lowe and Demi Moore. People hook up, break up, and struggle to find fulfilling jobs — you know the drill by now.
Medicine for Melancholy
Best known for The Daily Show, Wyatt Cenac stars in this 2008 indie about race and gentrification in the San Francisco hipster scene. Confronting the overwhelming whiteness of affluent, urban, and artistic communities, Medicine for Melancholy is a single-day story of the courtship between Micah (Cenac) and Jo’ (Tracey Heggins). It’s a more intelligent and critical take on contemporary hipsterism than many out there, and a hard look at the social scene many recent grads flock to once they’re off campus.
Proving that Jesse Eisenberg can play a character who isn’t a snotty nerd and Kristen Stewart can play a character who isn’t a bland audience surrogate, Adventureland follows an Oberlin grad’s efforts to fund his grad school education through a part-time job at an amusement park in Pennsylvania. It’s a sweet rendition of the ’80s summer romance, and the always-delightful Martin Starr plays Eisenberg and Stewart’s boss.
And now for some nonfiction! Kevin Roose’s book made a splash for its widely circulated chapter on a heinous secret society of Wall Street’s higher-ups, but most of it is concerned with banks’ lowest tier: straight-outta-college analysts working hundred-hour weeks at absurdly high pay. Young Money highlights a crucial cultural change in finance, which has turned from an industry for high-flyers unafraid of risk to a safe choice for grads petrified of the post-recession economy. If anything, Roose’s horror stories tell grads what not to do; the book’s a persuasive argument for avoiding an entry-level job that may pay well, but leaves those without massive debts or a genuine passion for finance miserable.