50 Shades of Nearly Grey
Midlife was made for the movies. All the drama of having been around the block once or twice (love, lust, loss, loneliness) is as heartfelt, grueling and cinematic a subject as it gets. The following 50 movies about midlife remind us that although we're sitting in the dark, we're not alone, and if we're lucky, maybe we can even learn a lesson or two. And we'll bring the popcorn. As always, we want to hear what your favorites are in the comments below.
Director: Adrian Lyne
Starring: Michael Douglas, Glenn Close
A wonderfully melodramatic, borderline kitschy telling of an adulterous affair turned deadly, and a movie which created a new screen archetype for future generations of filmmakers to play with to their heart’s content; the obsessive, stalking spurned-mistress/psycho-bitch, hereinafter affectionately referred to in pitch meetings as a “bunny boiler.”
Director: Joel Schumacher
Starring: Michael Douglas, Robert Duvall
Talk about being mad as hell and not taking it anymore; long before there was "Breaking Bad," there was Douglas, a disillusioned, white collar, middle-management type, divorced and utterly fed up with the soulless world about him; a world that seems to have lost not merely its sense of decency and compassion, but its need for him and those of his ilk, people whose rules for human behavior were steeped – at least in their minds – in a kinder, gentler, simpler time.
Bob & Carol & Ted & Alice
Director: Paul Mazursky
Starring: Robert Culp, Natalie Wood, Elliot Gould, Dyan Cannon
Only one well versed in the age-old traditions of Jewish child-rearing could have penned the line delivered when Ted, after having confided to Bob he feels bad about even thinking about having an affair, and therefore will not act on his carnal urges, is called an idiot by his good friend and told in no uncertain terms, “You’ve got the guilt anyway. Don’t waste it.”
The Squid and the Whale
Director: Noah Baumbach
Starring: Jeff Daniels, Laura Linney
If car chases, pyrotechnics and gratuitous sex are more your thing, this quiet, even somber little ‘80s-vintage drama and occasional comedy about a slowly dissolving family is not really for you; but if you want to see what midlife, adult disillusionment, and divorce look like through the eyes of a pair of insightful kids who can be (and often are) wise beyond their years, this baby’s right up your alley.
Director: John Cassavetes
Starring: Peter Falk, Ben Gazarra, John Cassavetes
Perhaps more than any other, this is the Cassavetes film many critics feel made him Godfather to all future generations of auteurs and independent filmmakers; a grainy, black & white cinema verité rendering of three middle-aged men who, almost as though they’re whistling past the graveyard, go on a drunken binge following the death of a fourth friend who, as you might expect, was just about their age.
Director: Frank Perry, Sydney Pollack
Starring: Burt Lancaster, Janice Rule
Back in college, when we first saw this odd little film based on a John Cheever short story (on network TV, no less), we thought the idea of a middle-aged man swimming from backyard pool to backyard pool across his suburban neighborhood was little more than a joke on acid; over the years, however, we’ve developed a greater appreciation for both the lyrical nature of Cheever’s allegorical tale and Lancaster’s guts in bringing it to the big screen; in fact, he would later call the film a favorite of his long career.
Director: Lawrence Kasdan
Starring: Kevin Kline, Danny Glover
If “The Big Chill” is Kasdan’s most pretentious, self-important film, this little gem might be his most human, a smart, feeling ensemble piece whose intersecting dominos start tumbling right off the bat when one of the central characters, a middle-aged immigration lawyer on his way home from a Laker game, takes a wrong turn, gets lost, finds himself in a life-and-death situation, and is rescued by an unwitting and unlikely hero.
Director: Mick Jackson
Starring: Steve Martin, Victoria Tennant
Martin wrote this modern-day adult fairy tale about his beloved City of the Angels; one that’s equal parts cynical and hopeful; a little fantasy, but just the right amount of reality; a film as much about the maddening quirks and tics of L.A. and its residents as it is about their inherent (but not always readily apparent) goodness.
Director: Albert Brooks
Starring: Albert Brooks, Debbie Reynolds
The first of a few Brooks films you’ll find on this list; this one about a twice-divorced, middle-aged sci-fi writer who moves back in with his mother and, in the process, gets taught a thing or two about what it takes to make a relationship work.
Director: Woody Allen
Starring: Woody Allen, Judy Davis
If Brooks is the Crowned Prince of midlife crises, Allen is the Lord and High Master. This is one of his most polarizing and deeply personal films, one that has an unflinching and often brutal sense of honesty that can at times smell a bit like self-loathing.
In Good Company
Director: Paul Weitz
Starring: Dennis Quaid, Topher Grace
Quaid is a 51-year-old ad salesman with no other job skills and a guy whose industry (magazine publishing) is circling the bowl. His new boss is roughly half his age. Yet that little nit pales in comparison to the fact that not only is his oldest daughter 18 years old, blossoming as a woman and readying herself to go off to college for the first time ... she’s Scarlett Johansson.
Director: Curtis Hanson
Starring: Michael Douglas, Tobey Maguire
Hanson followed his stunning “L.A. Confidential” with an artfully crafted and entirely nonjudgmental film about an aging professor riding the momentum of a best-selling novel he somehow managed to write a few years back, who now must come to grips with the harsh reality that, unlike most of his students, his best days are behind him and life no longer holds much promise.
Director: Albert Brooks
Starring: Albert Brooks, Jeff Bridges, Sharon Stone
A perhaps unfairly criticized film, once again by Brooks, in which the writer/director plays a Hollywood screenwriter whose inspiration has run dry, and who finds it mysteriously rekindled by a middle-aged beauty a friend suggests he visit, an alluring woman who suddenly and without warning gets the writer’s — and his wife’s — juices flowing again.
Director: Jim Jarmusch
Starring: Bill Murray, Jessica Lange, Sharon Stone
Murray brings the now-and-again daydream of many a less-than-fulfilled middle-aged man to life as a dour but one-time bon vivant/ladies’ man who, upon receipt of an anonymous letter informing him he has a son, is compelled to drive cross-country and seek out the four loves of his youth.
Director: Tom Hanks
Starring: Tom Hanks, Julia Roberts
A non-typical hodgepodge of a love story about an unassuming ex-Navy man who finds himself fired from a big-box retailer for hot having a college degree and a jaded, virtually sleepwalking woman, locked in a loveless marriage to a porn addicted freelancer, whose job at the community college is as much about refuge from her deadbeat mate as it is the paycheck she takes home to support him.
Eat Pray Love
Director: Ryan Murphy
Starring: Julia Roberts, Javier Bardem
A film for anyone still operating under the delusion that midlife crises are the sole purview of the male of the species; a woman one day drops everything, leaves it all behind, and sets out on an across-the-globe sojourn on which she will discover, among other things, the sensual pleasures of food in Italy, the power of prayer in India and the joys of inner peace among the islands of Indonesia.
Director: Alexander Payne
Starring: Paul Giamatti, Thomas Haden Church, Virginia Madsen
A divorced but still-in-love oenophile/English professor, whose first novel has become both a cause and crutch, travels to the Santa Ynez wine region on the eve of his friend’s wedding and, in the process, sees his actor pal for who he really is, gets his novel rejected, meets a beautiful, smart and soulful middle-aged woman, learns his ex-wife is never coming back and intentionally wrecks his car to help his narcissistic buddy conceal yet another serial indiscretion; but amid all this, he learns something about himself that might just turn out to be his salvation.
Director: Adrian Lyne
Starring: Richard Gere, Diane Lane
Almost a full generation after “Fatal Attraction” and "9 1/2 Weeks," Lyne – who seems to direct films with all the lurid sensitivity of a tabloid editor – was back exploring infidelity at the midpoint of an otherwise successful marriage, only this time with the wife as the offender; not to worry though, the husband is still left to clean up the mess.
Living Out Loud
Starring: Holly Hunter, Danny DeVito
A frank and bittersweet indie drama about a buttoned-down, highly driven woman who puts her plans on becoming a doctor on hold to try to help her husband get through med school, does so, gets jilted, despairs, starts drinking and then finds herself in the company of an underachieving middle-aged building superintendent/elevator operator who has nothing more to his name than a pipe dream, a gambling problem and a growing affection for her.
Director: Alexander Payne
Starring: George Clooney, Shailene Woodley
Clooney is a middle-aged Honolulu lawyer attempting to find his footing after a pair of haymakers to the chin: not only is his wife of two decades suddenly brain dead from a car accident, he’s just learned from his daughter that the comatose mother of his children had been having an affair with some unknown lover at the time of her accident.
Dan in Real Life
Director: Peter Hedges
Starring: Steve Carell, Juliette Binoche
As a screen actor, Carell’s ability to turn the flame down to a flicker and not telegraph what he is feeling (not to mention do or say) is a secret, frankly, that he should share with more than a few of his colleagues (Roger Ebert once called him “a low-key Jack Lemmon”) and, as a widower still struggling with his wife’s death four years after the fact, in this film he pulls that less-is-more acting thing of his off to intoxicating effect.
Under the Tuscan Sun
Director: Audrey Wells
Starring: Diane Lane, Sandra Oh
Part female fantasy, part yuppie porn, this Hallmark Card of a midlife film rides the coattails of Lane’s on-screen (and seemingly on-demand) ability to marry middle-aged beauty, gently muted charm and implied depth of character.
Everything Must Go
Director: Dan Rush
Starring: Will Farrell, Rebecca Hall
Based on a short story by the inimitable Raymond Carver, this is Farrell as you’ve never seen him before; another in a long line of unexpectedly deep and profound dramatic performances by an otherwise comedic actor who didn’t cut his teeth in acting class, but by doing live stand-up, living and dying on the strength of his own material, and sticking his head directly into the lion’s mouth, otherwise known as improv comedy.
Bread and Tulips
Director: Silvio Soldini
Starring: Licia Maglietta, Antonio Catania
A slightly plump and hardly beautiful (at least in the traditional sense) middle-aged housewife and mother is left behind when her bus, carrying her luggage, husband and children, takes off while she’s still fishing for her earring in a roadside ladies room, a fact that sets off one of the most endearing and effective road movies (and personal searches for love, fulfillment and meaning) in recent memory.
Lost in America
Director: Albert Brooks
Starring: Albert Brooks, Julie Hagerty
All the trailer for this wickedly funny satire needed was the scene with its two central characters – him, an ad man bypassed for a promotion who quits his job, and her, the ditzy, slightly mousy wife he’s convinced to bail on hers — behind the wheel of their brand spanking new, fully loaded and armed-to-the-bejesus Winnebago, while, in wry homage to both "Easy Rider" and the siren song of the open road, Steppenwolf’s “Born to Be Wild” growls in the background.
Return of the Secaucus 7
Director: John Sayles
Starring: Adam LeFevre, Gordon Clapp
Sure, it can get a little talky, rely too heavily on stereotypes and lack any sense of plot, but this low-budget cult favorite is historically significant, and not just because it was legendary indie director and Hollywood script doctor Sayles’ first-ever film (and script), it matters because it is the first of what would turn out to be a virtual parade of yuppie reunion/ensemble movies and TV shows that would rollout of Hollywood throughout the decade, not the least of which would be “The Big Chill,” which it predated by a full three years.
The Big Chill
Director: Lawrence Kasdan
Starring: Kevin Kline, Glenn Close
Thirty years after the fact, we marvel less at this beloved but sanctimonious blockbuster’s story, characters and soundtrack, and more at how director Kasdan perfectly captured the unmistakable vibe of each part of a reunion weekend; from the casualness, talkiness and catch-up nature of Friday night, to the genial anticipation of Saturday afternoon, the eating, drinking, dancing and rule-breaking that many times are Saturday night and, of course, the sleepy eyed amalgam of guilt, story-telling, disbelief, chuckles, resignation, knowing smiles and decision-making that can and often do define the subsequent Sunday morning.
Director: Richard Linklater
Starring: Ethan Hawke, Julie Delpy
In 1995’s “Before Sunrise,” they were two kids on a train on their way to self-discovery; in 2004’s “Before Sunset,” they reconnected in Paris nearly a decade later, a lot of water and missed opportunities under the bridge between them; and in this third installment of this most remarkable film cycle, Jesse and Celine are now husband and wife, and middle-aged parents trying like hell not to become just another sleepwalking couple who stayed too long at the fair.
Crazy, Stupid, Love
Director: Glenn Ficarra, John Requa
Starring: Steve Carell, Ryan Gosling
When it comes to uncertainty and midlife angst, if Carell has become Hollywood’s lonely hearted everyman and go-to guy, his costar in this smart little comedy, Marissa Tomei, has slowly emerged as his female counterpart, an actress whose vulnerability and talent for not so much showing pain, as hiding it, allow her to play aging women who are nearly, but not quite, ready to succumb to the years of heartbreak, women who seem to have a tenuous relationship with the pursuit of happiness, and women who have the uncanny knack for making us hope against hope they’ll one day find the peace and comfort they so richly deserve.
About a Boy
Director: Chris Weitz, Paul Weitz
Starring: Hugh Grant, Toni Collette
An unmotivated, financially set and terminally charming serial heartbreaker reaches midlife and suddenly finds his heart stolen from him – only not by a woman, but by the fatherless 12-year-old son of a lonely and perhaps suicidal woman who is best friend to one of his would-be conquests.
Director: Stanley Kubrick
Starring: James Mason, Sue Lyon
For years, the gold standard for midlife crisis movies; the first and hands-down finest screen adaptation of Vladimir Nabokov’s controversial 1955 novel about a scholarly and otherwise proper middle-aged man obsessed and eventually consumed by his desire for an alluring, underage vixen, who he starts bribing in exchange for her sensual presence in his life and, in time, her intoxicating, even addictive sexual favors.
Director: Blake Edwards
Starring: Dudley Moore, Bo Derek
At the time, it seemed all we wanted to talk about were Bo Derek, her beaded cornrows, her bathing suit, and her bouncy, slow-motion seaside jaunt toward the camera, but strip away all that eye candy and this Blake Edwards comedy reveals itself to be one of the funniest, most insightful explorations of a male midlife crisis we’ve ever seen, embodied, of course, by the inimitable Dudley Moore in the role that would make him a superstar on this side of the pond.
Director: Warren Beatty
Starring: Warren Beatty, Halle Berry
For such a handsome guy and such a notorious ladies’ man, Beatty sure made a lot of smart movies; like this one about an out-of-favor, middle-aged, borderline socialist of a U.S. Senator who one day decides to commit suicide after selling his vote on an insurance industry bill in exchange for $10 million policy on himself, says WTF, starts showing up at public functions drunk and using truth as his weapon, foregoing all pretense of decency and decorum and freely speaking his mind — becoming in the process, of course, one of the most popular politicians in the land.
Thelma & Louise
Director: Ridley Scott
Starring: Susan Sarandon, Geena Davis
Like “The Graduate,” “Pulp Fiction,”“Saturday Night Fever” and very few others, every decade or so a movie comes along that has a profound and unexpected impact on us — culturally, socially and otherwise — an impact that far exceeds the film’s artistry; this otherwise unremarkable story of two women pushed, literally, over the edge by a cruel, male-dominated world, who choose to react in a way that, until its release nearly a quarter-century ago, had pretty much been the exclusive territory the Y chromosome, is one such movie.
Last Tango in Paris
Director: Bernardo Bertolucci
Starring: Marlon Brando, Maria Schneider
To half the American moviegoing public, this wildly controversial tale about a middle-aged widower who, while still grieving, has a chance, violent and graphic sexual encounter with a young French woman, was little more than pornography disguised as art, to the other it was a compelling study of shifting sexual norms and a harrowing glimpse into the psyche of a man suddenly cast adrift at midlife; regardless, few who ever saw it will ever look a stick of butter quite the same way again.
Defending Your Life
Director: Albert Brooks
Starring: Albert Brooks, Meryl Streep
Brooks is at his bone-dry, angst-ridden best in this sweet little comedy, playing a self-possessed ad exec hit head-on by a bus who now must not only defend how he lived his life and negotiate his way past the pearly gates, but come to grips with the realization — even as he’s falling in love in God’s holding tank — that maybe his life wasn’t all that worth defending, and if given the chance he might have done things differently.
Director: Ron Underwood
Starring: Billy Crystal, Daniel Stern, Bruno Kirby
A movie set during a dude ranch cattle drive we liked less for its insights on life’s meaning and the characters’ reflections on their own defining moments, and more for how the three restless middle-aged men at the heart of the story could go off on tangents and riff on some of the era’s minutia, like the vagaries of the VCR, a wickedly funny little throwaway scene near the end of which one implores another to shut up, pleading with him, “He doesn’t get it. He’ll never get it. It’s been four hours. The cows can tape something by now.”
Director: Woody Allen
Starring: Woody Allen, Muriel Hemingway, Diane Keaton
Forget Allen, playing a 42-year-old twice-divorced writer dating a 17-year-old and setting his sights on his best friend’s wife; forget Hemingway, that 17-year-old, or Keaton, that best-friend’s wife — the real star of this love letter to the director’s beloved hometown is Manhattan itself, shot in stunning black and white, presented in panoramic 2.53:1 widescreen format, and graced by a score of some of the finest and most iconic Gershwin tunes ever.
Save the Tiger
Director: John G. Avildsen
Starring: Jack Lemmon, Jack Gilford
For as well as he could play fastidious, flustered and frenetic, the one emotion that Lemmon played better just about any actor in history was desperate; and in this dark, dreary story of an aging apparel executive desperately trying to wring one more season of relevance out of his decaying company before both he and it are put out to pasture is even harder to watch than “Glengarry Glen Ross,” which also stars Lemmon and which, in many ways, almost feels like a snarky parlor drama by comparison.
The Kids Are All Right
Director: Lisa Cholodenko
Starring: Annette Benning, Julianne Moore
A brilliantly written, acted and directed comedy/drama for our changing times; a film about a loving, caring same-sex couple and their kids, one of whom seeks out and finds his biological father, a charming, laid-back landscaper/sperm-donor whose presence suddenly complicates things on more levels than anyone dared imagine; and a film with so much heart, warmth, humor and humanity it should be required viewing for all budding homophobes and anti-gay marriage zealots.
Director: Brad Bird
Starring: Craig T. Nelson, Holly Hunter (voices)
Ever since he did “The Iron Giant” (one of the best movies — animated or otherwise — you’ve never seen), we’ve been big fans of Bird; but with this film, a whip-smart and fabulously entertaining story of a now-retired superhero trying unsuccessfully to not merely cope with midlife and his own expanding waistline, but to somehow manage all the corresponding trappings (marriage, fatherhood, the humdrum desk job, the cookie cutter house in the ‘burbs, etc.), the director/animation rock star somehow managed to exceed even our lofty expectations.
Director: Delbert Mann
Starring: Geraldine Page, Glenn Ford
Do not mistake this for hyperbole, but as a middle-aged, single and secretly lonely postmaster from Ohio who comes to New York every year for a convention and lights up lives and spreads joy wherever she goes, Page gives one of the single greatest screen performances in history — one that takes wing when, during one convention, her character encounters a kind, friendly, soon-to-be-wed bachelor, starts to develop feelings for him and finds herself inching out onto an emotional high-wire extending perilously over a deep, dark abyss full of hurt, loneliness and self-pity.
Leaving Las Vegas
Director: Mike Figgis
Starring: Nicolas Cage, Elisabeth Shue
A disillusioned shell of a middle-aged screenwriter comes to Vegas with the sole intention of drinking himself to death, and is doing quite a job of it until one day he meets a beautiful but emotionally maimed prostitute — the classic hooker with a heart of gold — with whom he establishes a friendship, a growing emotional connection, and most importantly, an uneasy agreement that she will not interfere with his reason for being there.
Up in the Air
Director: Jason Reitman
Starring: George Clooney, Vera Farmiga
A smart movie full of smart actors culled from a smart novel by a smart writer/director, this is the tale of a man who reaches midlife having spent his entire adult life living airport hub to airport hub, flying around the country firing people for a living and never once committing himself (or his heart) to anything (or anyone) real — and who now must face the music for having done so.
Director: Harold Ramis
Starring: Bill Murray, Andie MacDowell
If you were to divide Murray’s acting life into two halves, there’d be the terminally insouciant, wise-cracking wise-ass he always seemed to play as a young man and the somber, underplaying one-trick pony he settled into as an older one; one of the keys to this movie’s longevity and its continued power to entertain, if not inspire — besides its brilliant conceit and almost flawless execution — is the fact that as its linchpin, Murray bridged both halves of his acting life and seemed to borrow from the best of one while anticipating the best of the other.
The Seven Year Itch
Director: Billy Wilder
Starring: Tom Ewell, Marilyn Monroe
A perfect '50s-era fantasy in which a middle-aged editor from Manhattan — his wife and kids in Vermont on summer vacation — stays home to work, only to find his neighbor is a young actress who is exceptionally hot, both literally and figuratively; so much so she’s constantly in his air-conditioned apartment, she informs him she’s been storing her panties in the freezer to keep them cold, and on their way back from the movies she stands over a subway grate and holds her pleated white dress down at each side just as the train roars between her legs and sends a blast of cool air up her dress — much to her, his and, frankly, our delight.
Director: Darren Aronofsky
Starring: Mickey Rourke, Melissa Tomei
This moving and poignant little movie about an aging and broke wrestler trying to outrun some combination of fate, the future and his bad choices, served as a comeback vehicle for former bad boy, Mickey Rourke, while offering more reason to believe that Evan Rachel Wood, who plays his daughter, is just maybe (along with Jennifer Lawrence and Ellen Page) one of the three finest young actresses working today.
Life as a House
Director: Irwin Winkler
Starring: Kevin Kline, Kristin Scott Thomas
A tenderly told story about a fiercely unhappy, rudderless and only marginally successful architect who, upon learning he has terminal cancer, makes a vow to find it in himself, in what little time he has left, to become both the father and the man he’d always envisioned himself becoming.
The Ice Storm
Director: Ang Lee
Starring: Kevin Kline, Sigourney Weaver, Tobey Maguire
One of the best movies from one of the best years for movies (1997) in recent memory; Lee’s lyrical but suffocating period piece about a group of cynical, faithless people from the well-manicured and well-appointed suburbs of Connecticut (middle-aged adults and teenagers alike), all of them drowning in the emptiness of life and awash in a sea of infidelity, emotional restlessness and sexual unfeeling.
Director: Sam Mendes
Starring: Kevin Spacey, Annette Benning
A stunningly lyrical, visual midlife fantasy in which an ill-fated loser named Lester Burnham becomes a job-quitting, Pontiac Firebird-driving, fast food-serving, teenage-girl seducing rock star, liberating himself from all that once shackled him and becoming, in the process, a man as unafraid to die as he’d once been afraid to live.