The 99 Best Movies of 1999, Ranked

After the success of his 1994 low-budget hit Clerks and its more mainstream follow-ups Mallrats and Chasing Amy, slacker wonderkind Kevin Smith attempted this ambitious riff on Catholicism, which was deemed to be “polluted” by the American Society for the Defense of Tradition, Family and Property. The film’s Weimer Nineties casting is cute: Ben Affleck and Matt Damon are fallen angels trying to exploit a Papal loophole to get back into heaven; Chris Rock is a Black apostle written out of the Bible because of racism, Salma Hayek is a celestial muse turned earthbound stripper; George Carlin drops by as a New Jersey bishop trying to give the Church a cool new image; and Alanis Morrissette appears as God. By mish-mashing references to Star Wars, The Piano, and Home Alone in with its riffs on stuff like the Virgin Birth, Sodom and Gomorrah, and plenary indulgences, the movie also genuinely reflected the experience of Catholic kids raised in the Seventies and Eighties who’d transmogrified their ambivalence towards of the faith of their upbringing into an equally iconic embrace of a new moral system – the Church of Pop Culture. Today, we might call Smith’s attitude “lol something matters.” —Jon Dolan

You can understand why writer-director Troy Duffy’s crime thriller helped signal the end of a certain type of tough-guy movie that plagued the decade — even by the ’90s indie-filmmaker-watches-first-two-Tarantino-movies-too-many-times standards, the abundance of self-conscious flourishes, proto-edgelord offensiveness and performances for which “bad” is too kind a descriptive is a lot to take. But you also get why this film still has a cult following, especially once the Irish-American MacManus brothers (played by Sean Patrick Flannery and future Walking Dead MVP Norman Reedus) decide to go from South Boston ruffians to full-on vigilantes, one hail-mary at a time. Plus it has one of Willm Dafoe’s more gloriously eccentric performances, and considering we’re talking about this guy, that’s saying something. —David Fear

In West Canaan, Texas, they worship God, guns and the gridiron state champions known as the West Canaan Coyotes — just not in that order. In this community, star quarterback Lance Harbor (Paul Walker) is considered the second coming of Roger Staubach, and whatever Coach Bud Kilmer (Jon Voight) says is akin to gospel. As for the team’s second-string QB, Jonathan Moxon (James Van Der Beek), he’s content to warm the bench and read the paperback of Slaughterhouse Five he has stashed in his playbook. Then Harbor gets hurt, Moxon has to sub in, and he discovers firsthand the agonies and ecstasies of end-zone heroism. Director Brian Robbins’ fan favorite is best remembered today for its jock-jam soundtrack, the late Ron Lester’s performance as offensive guard/good ol’ boy Billy Bob, and extolling the seductive virtues of “whip-cream bikinis.” In terms of portraying high-school football’s cultural hold on Lone Star small towns, it isn’t fit to hold Friday Night Lights’ jockstrap. But it does give you a Hall-of-Fame sports movie villain in the form of Voight’s monomaniacal coach, whose tyranny on and off the field is truly terrifying. —D.F.

It may not reach the cinematic heights of his early classics Billy Madison and Happy Gilmore, but Adam Sandler’s contribution to the Class of ’99 features all the regular Sandler Players (Steve Buscemi as a bum, Rob Schneider as a delivery-man buddy) and hits all the reliable beats. To wit: Kinda-loser-with-heart-of-gold Sonny Koufax hatches a scheme to impress a pretty, accomplished woman, which involves cavorting around Manhattan with an “adopted” five-year-old son (played by twins Cole and Dylan Sprouse). While teaching the kid the joys of pissing on public buildings and tripping passing rollerbladers, Sonny ends up falling for a different very pretty, very accomplished woman — in this case, Nineties staple Joey Lauren Adams. Yes, the film’s attitude about the fairly random gay couple Sonny hangs with, while progressive-seeming at the time, reads much less so today. And yes, Sonny’s obsession with his friend’s fiancée (Leslie Mann) having waitressed at Hooters feels, dare we say, slightly misogynistic. But even at his knowingly frattiest, Sandler is nothing less than endearing. —Maria Fontoura

Wes Craven took a break from his master-of-horror duties to helm this based-on-a-true-story melodrama about Roberta Guaspari, a single mother who gets a job teaching the violin to kids in East Harlem. Everyone from her fellow teachers to the students’ parents are skeptical of what appears to be another stranger with a savior complex, until Guaspari ends up empowering these young musicians; when the successful program is later in jeopardy thanks to citywide budget cuts, a host of real-life virtuosos come to the rescue. After Scream became a hit, Craven leveraged his industry currency to convince his Miramax patrons he was the right man to bring this to the screen. The result feels like a lot of the other semi-schmaltzy the studio put out in the late 1990s, though it helps that Meryl Streep is playing Guaspari, and that everyone from Angela Bassett to Cloris Leachman to Gloria Estefan is filling out the supporting cast bench. —D.F.

Frank McCourt’s harrowing memoir of an Irish childhood characterized by poverty, hardship and tragedy got the prestige-lit event-movie treatment — it was released on Christmas Day in 1999 — and while it didn’t have quite the impact that the bestselling book did, it still left audiences dazed and reeling. No one would ever accuse Alan Parker (Midnight Express, Angel Heart, Pink Floyd: The Wall) of being subtle, and the director treats the squalor and the familial strife like he’s directing a war movie. What keeps this from devolving into standard poverty porn are the performances, notably Emily Watson as Frank’s long-suffering Ma; Robert Carlyle as his well-meaning drunk of a dad; Joe Breen as the young Frank (a literal poster boy, given that it’s his face peering out from a stark, black-and-white picture in the film’s marketing image); and Michael Legge as the teenage Frank, who manages to write his way out of hell and into heaven, i.e. the Statue of Liberty’s home. —D.F.

It will forever be known as the 007 movie starring Denise Richards as an American nuclear physicist named Christmas Jones. [Feel free to add your own snarky comment here.] Yet the 19th James Bond films, the third to star Pierce Brosnan, and the last time the MI6 agent was licensed to kill in the 20th century has its moments, including a riff on The Spy Who Loved Me‘s ski chase and Brosnan being both straddled and strangled by top-notch femme fatale Sophie Marceau. Throw in Robert Carlyle’s Renaud, a chilling variation on the unfeeling Bond villain in that he literally has lost his sense of touch, Robbie Coltrane reprising his Goldeneye Russian mobster and the longest pre-credits sequence in the series’ history, and it’s enough to make you forget the franchise was in danger of running in fumes. (You know this is a very much a late ’90s entry as well, given that Goldie plays a henchman and you can hear turntablist scratching added to John Berry’s theme music.) Brosnan would play Bond one more time, in 2002’s Die Another Day, before ceding the role to the actor who’d recast the iconic character for the 21st century. —D.F.

You can’t overstate the cultural saturation of Austin Powers in the late Nineties — he shagged the zeitgeist, baby! Mike Myers and Jay Roach created a global obsession with the Swinging London spy who got frozen in 1967, then defrosted to battle his nemesis, Dr. Evil. The original 1997 Austin Powers: International Man of Mystery was a comedy polished with love and finesse, and while the summer-of-’99 sequel was an obvious bash-it-out quickie, it was still popcorn-pukingly funny. You got Myers once again doing double duty; Heather Graham as CIA agent Felicity Shagwell; Verne Troyer as Mini-Me; a music interlude from Burt Bacharach and Elvis Costello, a lunar base divided into Moon Unit Alpha and Moon Unit Zappa; Madonna’s “Beautiful Stranger”; and the Russian assassin Ivana Humpalot. The third Powers entry may have sunk the franchise, but this second one kept the grooviness factor on 10. —Rob Sheffield

A.K.A. the movie in which a pre-Iron Man Robert Downey Jr. gets slapped by Mike Tyson — and that’s maybe the fifth or sixth wildest thing that happens in writer/director/accused sexual predator James Toback‘s satire on race, celebrity, and cultural appropriation. Brooke Shields is a documentary filmmaker making a movie about the impact of Black culture on white teens; Ben Stiller is a corrupt cop trying to get a basketball player (portrayed by New York Knicks’ Allan Houston) to throw a game; everyone from Claudia Schiffer to members of the Wu Tang Clan show up at one point another and improvise scenes. It’s the sort of film that opens with an explicit interracial threesome in Central Park and only gets more messy, outrageous and provocative from there. It’s unforgettable, at the very least. —D.F.

A 17th-century Italian violinmaker believes he has finally crafted the perfect instrument — then tragedy strikes, and after varnishing it in a blood-red hue, he demands this cursed item be stricken from his sight. Over the next few centuries, the violin will change hands a number of times, and end up affecting the lives of German child prodigy, a British wastrel, a Chinese apparatchik and an American appraiser (Samuel L. Jackson) who becomes obsessed with this legendary instrument when it comes up for auction. This multinational production from French-Canadian filmmaker François Girard (Thirty-Two Short Films About Glenn Gould) is a good example of the extravagant, globetrotting costume dramas that filled arthouses throughout the decade, and gives Jackson a nice chance to play against type. —D.F.

“I killed the teen dream. Deal with it.” With these gentle words, Rose McGowan takes her place in history as the teen-movie villain-queen canon. McGowan, Julie Benz, and Rebecca Gayheart play a trio of mean girls who rule the halls of Reagan High, until they accidentally snuff a rival with a piece of candy. It was arguably the darkest teen comedy since Heathers — and it remains one of the funniest. Writer/director Darren Stein made this a nonstop barrage of Wildean bitch-quips (“I don’t believe we’ve met, what with the cruel politics of high school and all”) and Nineties fashion. Plus it’s got a hell of a soundtrack, too, with the Donnas rocking the prom. McGowan chews up her “Satan in heels” role, especially when she orders her minions, “You are gonna walk into that school and strut your shit down that hallway like everything is peachy fucking keen!” —R.S.

Martin Scorsese reunited with his Taxi Driver screenwriter Paul Schrader for yet another nocturnal tour through the mean streets of New York City, and this time God’s Lonely Man isn’t a cabbie but a paramedic, perpetually working the graveyard shift and perilously perched on the edge of sanity. As played by somewhat restrained (for him) Nicholas Cage, this burnt-out EMT keeps hallucinating the ghost of a young woman he couldn’t keep from flatlining and getting paired with a series of increasingly more unstable partners. Salvation comes in the form of Mary (Patricia Arquette), who our hero meets during a call involving her father, but even she can’t totally save his soul. The closest thing to God in this world is a dispatch operator who keeps sending them through Gotham’s seven circles of hell, and is blessed with the voice of Scorsese himself. It’s a flawed movie, to be sure, yet it’s still proof that even the auteur’s minor works can still be wild rides. —D.F.

To say that time has not been kind to the Best Picture Oscar-winner of 1999 would be the understatement of the year — and that notion still applies even if you don’t factor what’s happened regarding the movie’s lead actor in the past seven years. Sam Mendes’ satirical look at the “perfect” American family was considered a significant statement on the fragile, fractured mindset of the paterfamilias at the end of the American century, and while you wouldn’t call Lester Burnham’s midlife crisis aspirational, the movie definitely treats regression back to his teen self as something like suburban liberation. The shot of a plastic bag whirling in circles, courtesy of Wes Bentley’s boy-next-door videographer, is no longer a shorthand for existential ennui or finding the finding the beauty in the mundane; the movie’s signature image of a teenage cheerleader naked under roses, however, has become twice as icky. Even at the time, the idea that this was the standout movie of a standout filmmaking year felt questionable. Yet it still went home with five Oscars, so…. —D.F.

The MCU was not even a glint in Kevin Feige’s eye when this parody of superhero teams — sprung directly from the pages of Bob Burden’s Flaming Carrot Comics — hit screens in the middle of ’99. (For context: The first X-Men movie was still a year away from being released.) When the beloved do-gooder Captain Amazing (Greg Kinnear) is kidnapped by his nemesis Casanova Frankenstein (Geoffrey Rush), Champion City suddenly finds itself without its main champion. For such Grade-Z superheroes as Mr. Furious (Ben Stiller), the Blue Raja (Hank Azaria) and the Shoveler (William Macy), however, this is finally the opportunity to prove they belong in the big leagues. Quicker than you can “Avengers Assemble!”, they’ve recruited a handful of equally ambitious also-rans under the moniker “Mystery Men” — such as Invisible Boy (Kel Mitchell), the Bowler (Janeane Garafalo) and Spleen (Paul Reubens), whose superpower is toxic flatulence — and try to save the day. At the dawn of the new millennia, this was a mildly funny comedy with a handful of alt-comedy and A-list talent. Now, in an age when every third-tier Marvel group gets their own franchise, it’s a hundred times more hilarious. —D.F.

Walter (Robert De Niro), a bigoted retiree who suffers a stroke, must learn to regain his speech by seeing a singing coach, a transgender woman named Rusty (Philip Seymour Hoffman). The odd-couple pairing, was one of the first Hollywood movies to focus on trans characters, a community that filmmaker Joel Schumacher had observed firsthand. (“The people that inhabit Flawless are very real for me,” the writer-director said. “Schumacher, “These are interesting communities and people pass them by without even noticing them.”) With modern eyes, we can see how this film would be made differently today — for instance, a trans actor would play Rusty, although Hoffman’s performance is exceedingly lovely and nuanced, eschewing stereotypes. Nonetheless, the movie stands as a bold step into a world that, to that point, mainstream American cinema had been too timid to touch. —Tim Grierson

Spike Lee returns to the long, hot New York summer of 1977, when a serial killer known as “the Son of Sam” had everyone in the five boroughs on edge. If you’ve read Jonathan Mahler’s invaluable history Ladies and Gentlemen, the Bronx Is Burning, then you know this was a crazy year, from the Yankees’ Reggie Jackson breaking records to looters breaking shop windows during an epic blackout. For Lee and his cowriters Victor Colicchio and a pre-Sopranos Michael Imperioli, all that terror and chaos was mostly a good excuse to dive into cultural divides and the neighborhood tribalism that’s still part of NYC’s DNA. It’s a bit of a spirit-of-’77 hodgepodge, complete with disco and punk scenes, a Plato’s Retreat interlude, and the era’s paranoia dialed up to 11, along with a straight-outta-early-Scorsese storyline in which John Leguizamo’s nice Catholic hairdresser struggles with a serious Madonna v. Whore complex. Both the camerawork by Ellen Kuras and the acting — notably Adrien Brody as a part-time male hustler and full-time CBGB’s habitue, and Mira Sorvino and Jennifer Esposito as two Brooklynites navigating respectively rocky relationship terrain — keep this from devolving into late ’70s cosplay. —D.F.

Many were thrown by the fact that David Mamet, the poet of the four-letter word, would be interested in something as genteel as Terence Rattigan’s play, set in upper-crust England in the 1910s. But at heart, Mamet has always cared about ethics and behavior — why we’re drawn to do the things that we do — and so it was no surprise that his adaptation would focus on moral codes and the sinister strictures of social mores. Sir Robert Morton (Jeremy Northam) is a renowned defense attorney hired to represent Ronnie Winslow (Guy Edwards), a teenage naval cadet accused of stealing a postal note, resulting in his expulsion. This is no simple courtroom drama, however, with Mamet equally focusing on how the trial affects the Winslow family — in particular, the boy’s prideful father (Nigel Hawthorne), who risks his reputation on the word of his son. Nobody drops a F-bomb, but the man behind Glengarry Glen Ross and The Spanish Prisoner remains fixated on duplicity, self-deception, and how the people around us are far more unknowable than we could possibly grasp. —T.G.

Celebrated author John Irving adapted his own bestselling novel, which tells the story of Homer Wells (Tobey Maguire), who grows up in an orphanage in Maine. The doctor who runs the home, Wilbur Larch (Michael Caine), also performs secret abortions, and trains young Homer, a reluctant pupil, in obstetrics. After Charlize Theron’s Candy shows up (on the arm of Paul Rudd, in a rare dramatic role as a World War II fighter pilot) in need of Larch’s services, Homer is suddenly inspired to leave the orphanage and experience life — which includes apple-picking (for work), fornicating with Candy (for pleasure), and uncovering dark family secrets about his fellow pickers that compel him to use his ill-begotten doctoring skills. Directed by Lasse Hallström, the film won Irving a screenplay Oscar as well as a second Best Supporting Actor statuette for Michael Caine. But its most lasting contribution to the culture may be Larch’s ritual bedtime farewell to his charges. Say it with us now: Good night, you princes of Maine, you kings of New England. —M.F.

A frustrated writer (Jeremy Theobald) begins pathologically stalking random strangers on the streets of London, partially out of a need for inspiration and partially out of boredom. One of his marks turns out to be a thrill-seeking thief named Cobb (Alex Haw), who is less interested in stealing things for profit than the perverse glee of disrupting people’s lives. Soon, the stalker is recruited to join as a partner in crime. Then he spies one of their victims in a bar — a sultry blonde (Lucy Russell) — and decides on a whim to approach her. Nothing is ever quite what it seems here, however. Made on a shoestring budget and shot in black & white, this modest, clever thriller played a few festivals and got a brief run in the spring of ’99. It might’ve been just another one of those come-and-go indie projects were it not for the fact that its first-time filmmaker, a 28-year-old named Christopher Nolan, was about to become one of the defining writer-directors of the 21st century. And when you watch this inside-out neo-noir now, you can see that so many of the thematic obsessions and stylistic tics associated with the Oscar-winner’s work were all there, right from the very beginning. —D.F.

Every screenwriter faces two great fears: losing their edge and losing their position in an industry that already treats them like lepers. Stephen Phillips, the sad-sack scribe at the center of writer-director-comic genius Albert Brooks’ comedy, happens to be dealing with both issues at once. Luckily, his best friend (Jeff Bridges) thinks he has the solution: work with a muse — it turns out they’re real! — who can help get his career back on track. Then Phillips meets this high-maintenance mythological woman played by Sharon Stone, and every aspect of his life is completely thrown into chaos. Brooks’ farce works better as a satire of Hollywood fickleness than a self-directed star vehicle for his neurotic persona (Martin Scorsese’s rant about remaking Raging Bull, “but with a thing guy… like, really thin!” remains a hilarious self-own, while the joke in which James Cameron is advised to “stay away from water” plays 20 times funnier post-Avatar sequel). To say Stone steals the movie suggests that Brooks didn’t hand this to her on a silver platter from the get-go; the divine-diva-run-amuck role feels tailor-made for her strengths as a comedian, and dear Zeus, does she ever make the most of it. —D.F.

It’s a scenario familiar to most of us: One minute, you’re making sweet, sweet love to your husband on your expensive boat, the next you’re waking up with his blood all over you, he’s nowhere to be found and the cops, unsurprisingly, have lots of questions. This revenge movie became one of the big surprise hits of 1999, and helped establish Ashley Judd as a name-above-the-title lead outside of the Indiewood world. Accused of murdering her spouse, her everywoman is sent to prison, only to discover that — spoiler alert! — her husband (Bruce Greenwood) faked his death and left her to take the fall. Thanks to the titular legal ruling, she can’t be convicted for the same murder twice, which clears the path for her to hunt him down and actually kill the rat bastard. Meanwhile, her parole officer Tommy Lee Jones, who has plenty of experience hunting down fugitives, is hot on her trail. Is it ridiculous? Of course! Is it also the sort of late ’90s star B movie that turns solid actors into A-list movie stars, and makes you miss when these kind of films were part of a well-balanced moviegoing diet? Also yes! —D.F.

Disney’s big animated movie of ’99 wasn’t a fairy tale, an ancient fable, or a princess-driven musical — instead, they opted for a tween-friendly take on Edgar Rice Burroughs’ famed king of the jungle. Raised by Glen Close’s motherly ape, the man-cub will grow up to sound like Tony Goldwyn, look like Eddie Vedder circa Ten and have the agility of Tony Hawk on a half-pipe. Everything’s hunky-dory until British explorers show up, complete with a hunter intent on bagging and selling the jungle’s simian residents. On the plus side, they’ve also brought a comely young lass named Jane (Minnie Driver) and, well, you know the rest. We may eventually forgive the soundtrack’s insipid Phil Collins’ song “You’ll Be in My Heart” for winning the Oscar over “Blame Canada!,” though that day won’t be today. But awards snafus aside, the Mouse House’s animation is particularly on-point, the set pieces move like gangbusters (see: this fight between Mama Ape and a leopard over Lil’ Tarzan) and Driver gives her heroine the perfect mix of wit, grit and romantic grace. —D.F.

It was the end-of-the-decade romp that set out to be a mash-up of every teen rom-com ever made—it’s practically a Now That’s What I Call High-School Prom Movies! sampler. But it’s pure charm, thanks to the power couple of Rachel Leigh Cook and Freddie Prinze Jr. It’s your basic Pygmalion-via-Breakfast Club makeover: Can the misfit art student turn into the prom queen just by taking off her glasses? Can the hero make a stupid bet but still win her heart at the end? Can you imagine a high school with Kieran Culkin, Paul Walker, Anna Paquin and Lil’ Kim? And most importantly, can Usher play the prom DJ who sends everyone home happy with “The Rockafeller Skank”? The answers are: Yes, yes, yes, and check it out now, the funk soul brother. She’s All That was the last movie Gene Siskel ever reviewed; he came through with his final thumbs-up. —R.S.

Jim Carrey went full Method-acting madness to play divisive comedian Andy Kaufman; he was so devoted to diving into the role that, in fact, that he drove everyone from his fellow cast members to director Milos Forman around him on set crazy. (Costar Danny DeVito looks like he’s ready to slug him at any moment.) The performance and the biopic remain remarkable, however, with one genius paying homage to another. Kaufman cannonballs from one outrageous subversion of celebrity niceties to another, from wrestling women to reading the entirety of The Great Gatsby to an audience in defiance of his club audiences. Few artist portraits are as playful or as combative, offering no middle ground for the viewer — you’re either on Kaufman’s (and Carrey’s) uncompromising wavelength or your sense of humor needs a tuneup. In a decade in which “selling out” was still considered a sin, Man on the Moon found hilarity and poignancy in an unapologetically joyous original insisting on being himself. —T.G.

The star of Bull Durham and Field of Dreams returns to the mound for one more affectionate ode to America’s pastime. You don’t need to know a splitter from a 98-mile-an-hour heater to appreciate the salty pathos Kevin Costner brings to Billy Chapel, an aging Detroit ace looking to close out his career with a perfect game — that is, if he can keep his mind from wandering to Kelly Preston’s dream-girl-who-got-away, introduced through flashbacks that lay out the bumpy course of their romance. Sam Raimi, the Evil Dead maverick calling the pitches, forgoes his usual demonic fastball in favor of a style as relaxed as a Sunday on the couch with a double header on the tube. It’s a right-down-the-middle Dad Movie — and a nice victory lap for an actor who always looks at home with his eyes on home plate. —A.A. Dowd

Fresh off her visually stunning, Tony-winning Broadway adaptation of The Lion King, director Julie Taymor attacked the big screen with an equally bold vision, turning one of Shakespeare’s least-loved tragedies into a striking, absurd extravaganza. Anthony Hopkins, at his most scene-chewing virtuosic, makes a meal out of Titus Andronicus, the mighty Roman general who returns home victorious after slaying the Goths, his impetuous execution of the eldest son of the defeated Goth regent Tamora (Jessica Lange) backfiring when she becomes Queen of Rome, setting the stage for a series of increasingly twisted reprisals between the two combatants. Written when the Bard was young and looking for a bloody, gruesome hit that would strike a chord with the masses, Titus Andronicus lacks the elegance of his later masterworks like Hamlet or King Lear. But Taymor’s visual flair, cheeky irreverence and inspired extravagance argue that it may be Shakespeare’s most shamelessly entertaining drama. In her impertinent, lavish retelling, revenge is a dish best served cold — and also with a bit of a wink. —T.G.

There had been screen adaptations of August Strindberg’s 1888 drama about the sexual tension between a Count’s daughter and her father’s personal valet both before and after director Mike Figgis (Leaving Las Vegas, The Loss of Sexual Innocence) gave us his interpretation, including a well-respected 2014 movie starring Colin Farrell and Jessica Chastain. But there’s something about this ’99 iteration, starring Saffron Burrows as the title character and Peter Mullan as the object of her fancy and her cruelty, that taps into the more feral aspects of the story’s master-and-servant dynamic. The handheld camerawork only ups the instability of the situation, making you feel as if everything will either explode or unravel at a moment’s notice. It’s proof that the play could still be a powder keg more than a century after the fact. —D.F.

The 1990s were a weird decade for Woody Allen. (We’re talking professionally — personally is a whole other discussion.) He made some of his biggest hits (Bullets Over Broadway, Mighty Aphrodite), one bona fide masterwork (Husbands and Wives), and a lot of miscellaneous debris. But he closed the 20th century out on a surprisingly high note, with this cross between a mockumentary about a fake jazz -guitar legend named Emmet Ray (Sean Penn) and an oddball rom-com. A contemporary of Django Reinhardt, Ray is talented jerk with big ideas; you wouldn’t think he’d fall for the mute laundress (Samantha Morton) he meets at the beach, and yet they make for a cute couple. It’s only later that he realizes she’ll be the one who got away, and that heartbreak makes for good artistic inspiration. And while Penn provides the proper amount of lowdown, it’s Morton’s absolutely sweet, silent-comedy take on his object of affection that truly makes the movie work. —D.F.

Oscar Wilde’s 19th century play gets a late-20th century Miramax makeover, complete with Masterpiece Theater-worthy production design, a Brit cast who excelled in adding extra bite to Wilde’s witty bon mots (lookin’ at you, Rupert Everett and Jeremy Northam) and a host of late 1990s stars (Julianne Moore, Minnie Driver, and a positively babyfaced Cate Blanchett). Everett’s Lord Goring, “the idlest man in London,” wants nothing more than to traipse around the city and indulge in his every lascivious whim. Then a blast from his past, Mrs. Cheverly (Moore), shows up, with political maneuvers, blackmail and revenge on her mind. “Are you not just a little bit please to see me?” she asks Goring. “Possibly even less than that,” he replies. If you just tittered a little reading this as you took a sip of Earl Grey tea, then this adaptation is most certainly for you. —D.F.

Joe (David Strathairn), a small-town Alaska handyman, is trying to live down a tragic mistake from his past. He falls for a singer, Donna (Mary Elizabeth Mastrantonio), who’s dealing with her own emotional baggage. The limbo of the title refers not just to this frozen hinterland but to the hesitant main characters who risk giving love a try, only to have their lives upended by a shock twist involving Joe’s brother. As always, filmmaker John Sayles has a sharp eye for the customs and rhythms of the world he chronicles, which give this movie a richness that extends to the weathered, weary performances from Strathairn and Mastrantonio. As for the film’s divisive ending, it speaks eloquently to the anxiety of the unknowns that await us all — from day to day, we’re never sure if we’re living in a gentle comedy or a dark thriller. —T.G.

Some advice to filmmakers hoping to turn classic kids-lit into memorable movies: Get Michael J. Fox to voice your animated, anthropomorphized heroes. The former Marty McFly is the definitely the secret sauce that makes Rob Minkoff’s take on E.B. White’s famous book — about a tiny white mouse who is adopted by humans, and must eventually choose between his biological rodent parents and his new Homo sapien family — work way better than you’d expect it to. There’s an innocence and joy he brings to his miniature CGI hero, especially in scenes with his initially reluctant new brother Jonathan Lipnicki, as well as a pathos to lines such as “I feel an empty space inside me, and I just wanna know what was there before.” The rest of the cast is nothing to sneeze at, of course — this breezy, enjoyable kids’ flick is the answer to the trivia question, “What movies features the talents of Geena Davis, Hugh Laurie, Nathan Lane, Chazz Palminteri, Dabney Coleman, Steve Zahn, Jennifer Tilly, Julia Sweeney, Brian Doyle-Murray, Estelle Getty, David Alan Grier, Bruno Kirby and comic legend Stan Freberg?” But it’s Fox who gives this “little” movie a big heart. —D.F.

Starting with its extended, single-shot opening — which immediately connects the dots between the theater space, the politically active artist and trod-upon everyday people — writer-director Tim Robbins’ boisterous drama shows that its willing to risk wearing both its ambitions and its intentions all over its sleeve. Combining the behind-the-scenes workings of the Federal Theater Program, Orson Welles attempt to stage the lefty musical The Cradle Will Rock for the FTP, and Nelson Rockefeller’s commissioning of Diego Rivera to paint a mural in the lobby of Rockfeller Center (along with a few other burbling subplots), this look back at the complicated relationship between commerce, the arts and agitprop is itself a work of agitprop, sounding the alarm about what happens when creative types cozy up to corporate bigwigs. Robbins raided his Rolodex for the fit-to-burst ensemble cast, which includes Bill Murray, Cherry Jones, Hank Azaria, Emily Watson, Susan Sarandon, John Turturro, Paul Giamatti, Vanessa Redgrave, Rubén Blades, two Cusacks (John and John) and both members of Tenacious D. And while no one would accuse it of being anything less than unganily, it’s the sort of overly sincere big swing we could use more of right now. —D.F.

“Just what the hell did you do to the sharks!?” asks Samuel L. Jackson, with the same booming outrage he’d later reserve for motherfucking snakes on a motherfucking plane. The pseudoscientific answer to his question might have put a toothy grin on Michael Crichton’s face. Crossbreeding Jaws with Jurassic Park, junk-cinema maestro Renny Harlin unleashes a school of brainy maneaters — some brought to life via the prehistoric wonder of animatronics — on a water-logged research facility. The improbabilities mount faster than the bodies. Is that Michael Rapaport as a brilliant scientist? Did that shark just try to cook LL Cool J in an oven? What gives this glorified B-movie some real bite is the merciless glee in which it chows down on its overqualified cast. No role is so big that it guarantees survival. No monologue is so inspirational that it can’t be ferociously cut short. —A.A.D.

Tim Burton applies his Grand Guignol mall-goth vibes to Washington Irving’s short story, about a hapless man named Ichabod Crane who has a first-hand encounter with local urban legend “the Headless Horseman.” This time around, Crane gets promoted from schoolteacher to a New York City police constable sent upstate to investigate a series of mysterious decapitations; he also goes from the gangly, lanky figure of the Disney cartoon to resembling Johnny Depp, who pairs well with Christina Ricci’s pale-skinned heiress Katrina Van Tassel. The vibe here channels a lot of vintage Hammer horror and the 1960s Edgar Allan Poe cycle of films from American International Pictures, and while the overal pedigree is strong (Francis Ford Coppola is an executive producer, Seven‘s Andrew Kevin Walker wrote the screenplay and god-tier cinematographer Emmanuel “Chivo” Lubezki shot it), it’s very much a Burton film from start to finish. —D.F.

In the West Virginia town of Coalwood circa 1957, you either work in the mines or you teach kids who will eventually grow up to work in the mines. You don’t usually go on to become a rocket scientist. But young Homer Hickam — look how baby-faced you were, Jake Gyllenhaal! — watches the recently launched Sputnik go blazing through the night sky, he suddenly becomes obsessed with building his own rocket. His friends and the school brainiac help him build miniature prototypes. His working-class father (Chris Cooper, in is his other big toxic-repressed-male role of ’99) disapproves of such foolishness. A kindly teacher (Laura Dern) thinks this project will not only take him to the national science fair, but possibly be his ticket to a brighter future. Director Joe Johnston also made The Rocketeer, so he’s clearly down for the cause as well. A lovely biopic about a real-life dreamer — Hickam would becoime a real-life aerospace engineer at NASA — which adds a nice bit of grit to its Norman Rockwell-esque Americana. —D.F.

Before she was Carmela Soprano, Edie Falco gave us the title character in Eric Mendelsohn’s black-and-white indie gem: an aspiring actor with a unflappably upbeat attitude. She’s on her way to make it big in the moving pictures in Hollywood, USA, i.e. the same Tinseltown that just chewed up and spit out her old high school crush, a would-be filmmaker named David (Aaron Harnick). Meanwhile, both of their respective sets of parents — including the great Madeline Kahn, in her final film role — seem to be stuck living lives of quiet desperation and an extremely symbolic eclipse is enveloping their hometown of Babylon, Long Island, in darkness. It’s a great example of how the New York wing of late-1990s independent filmmakers were combining the wry DIY aesthetic of Hal Hartley, etc., with the whimsical humanism of their Park City cohorts. That Mendelsohn’s character study won him the Best Director award at that year’s Sundance isn’t the least bit shocking. —D.F.

Ralph Fiennes had already demonstrated he was an expert at showing simmering passions coming to a spilling-over boil courtesy of The English Patient three years earlier — and for this adaptation of Graham Greene’s novel about jealousy, adultery, and Catholic guilt, he happily turns the temperature up even further. Tracing an on-again, off-again obsession intertwined with WWII, this look at the fallout of a tempestuous affair between Fiennes’ novelist and Julianne Moore — who’s the wife of an old acquaintance — balances prestigious stiff-upper-lip period drama with explicit scenes of two lovers in a mutual state of heat. Indeed, there may not be a more dizzying, swoon-worthy moment in either actor’s filmography (or director Neil Jordan’s back catalog) than the couple walking out a restaurant after a faux-polite conversation and suddenly kissing each other compulsively under a raincoat. And as in Greene’s novel, there are matters of faith that complicate their infidelity, adding a whole other layer to their unbridled lust during wartime. —D.F.

The tagline for Ang Lee’s stab at a Seventies-style revisionist Western set during the Civil War was that soldiers “didn’t fight for the Blue and the Gray… they fought for their friends and their family.” It helps set the context for his unusual, highly visceral take on the War of Southern Aggression, given that we’re asked to ride with pro-Confederate guerrillas like Quantrill’s Raiders and Missouri’s “Bushwhackers” — any recognizable, binary notions of good-vs.-evil and us-vs.-them get muddied from the moment the movie hits the ground running. The scenes of battle aren’t designed to be rah-rah rousing, and in following Tobey Maguire’s young, German immigrant (who takes up the Confederate cause out of revenge) and Jeffrey Wright’s former slave as they seek shelter in between raids, you get to see their more personal conflict play out off the battlefield as well. Kudos go to singer Jewel Kilcher as well, who makes the most of her role as a widow who crosses their path. In a year filled with so many extraordinary movies across the board, it was easy for something like this to fall through the cracks. Now that Lee’s longer “director’s cut” is out in the world, this is one of those ’99 movies ripe for rediscovery. —D.F.

Who better to tackle Herman Melville’s 1852 novel Pierre; or, the Ambiguities — a “curiosity of literature” filled with sex, subversiveness, and a warped spirituality that had critics calling its creator immoral — than a filmmaker who understood what it was like to push envelopes and piss off tastemakers? Like the Moby Dick author, Leos Carax was coming off a magnum opus (1991’s The Lovers on the Bridge), and the French writer-director’s adaptation manages to tap into his romanticism (capital and lowercase R versions) and a palpable sense of rage. Pierre (Guillaume Depardieu, a.k.a. Gérard’s kid) has a doting mom (Catherine Deneuve), a fiancé (Delphine Chuillot), and a successful novel under his belt. Then, one night in the forest, he encounters Isabelle (Yekaterina Golubeva), and falls so head-over-heels for her that not even the disclosure that she’s his half-sister can stop them from an amour most fou. What follows is extremely un-simulated sex, a waterfall of blood, some incredible Scott Walker songs, and the sense that you’ve either witnessed the demented work of a genius or the work of a demented genius. We favor the second one. —D.F.

Based on Denis Johnson’s short story collection, this stark, starling indie film follows FH (Billy Crudup), a junkie flailing through the 1970s, eventually clawing his way to recovery. Premiering at Telluride in 1999 and released in the States the following year, the movie is raw but funny, seeing in its shambling protagonist the sort of idiosyncratic antihero who wouldn’t have been out of place during the New Hollywood era. The supporting cast features a who’s who of dazzling character actors and rising stars, including Samantha Morton, Denis Leary, Jack Black, and Michael Shannon. But the focus is always on how heroin’s promise of transcendence is undermined by the ugliness of all it takes from its luckless users. —T.G.

What, you thought Tony Soprano had a lock on the whole Mafia-boss-goes-to-therapy racket? This Robert De Niro and Billy Crystal comedy, about a Cosa Nostra capo getting in touch with his feelings thanks to a reluctant, neurotic shrink — we’ll let you guess which actor portrays which character — hit theaters a few months after HBO’s flagship series premiered. But the idea had been percolating way before Tony started freaking out over a family of ducks, and plays the idea of a tough-guy gangster not for pathos but strictly for laughs. It helps that the legendary Harold Ramis is calling the shots (he also contributed to the script alongside Kenneth Lonergan and The Larry Sanders Show writer Peter Tolan), and that De Niro also seems to be having a blast both channeling and making fun of his past Mob-movie turns. To paraphrase the man himself: You’re good, you. You are very good, Analyze This. Read it in a De Niro voice and it sounds better. —D.F.

Following a prolific period in the 1980s when he produced several classics in quick succession, including Castle in the Sky and My Neighbor Totoro, legendary Japanese animator Hayao Miyazaki went five years between 1992’s Porco Rosso and this epic fantasy tale, and you can feel the effort and care in every frame of the film, which made his allegiance to the natural world as overt and impassioned as any in his remarkable, environmentalist oeuvre. Set in medieval Japan, Princess Mononoke chronicles a growing conflict between the human world and the spirits who protect the forest — in the middle of that feud is a noble prince, Ashitaka, who’s on a journey to rid himself of a terrible curse. This beautifully hand-drawn drama — the lengthiest of Miyazaki’s films — took two years after its Japanese premiere to finally reach the United States, where it was released by Miramax’s Harvey Weinstein, who dared to suggest trims to the master. Thankfully, Miyazaki wasn’t having it. “I did go to New York to meet this man, this Harvey Weinstein,” he recalled in 2005, “and I was bombarded with this aggressive attack, all these demands for cuts.” With great pride, Miyazaki added, “I defeated him.” —T.G.

George Festrunk and Mr. Robinson, together at last! Frank Oz’s sublimely silly showbiz satire casts Steve Martin as a modern Ed Wood shooting a Z-grade science fiction opus guerilla-style, with a movie star who doesn’t even know he’s in the movie. Eddie Murphy is that star, a vain, flaky A-lister being clandestinely filmed (read: stalked) by the amateur production. Murphy also plays the actor’s nerdy twin brother — an inspired bit of dual casting that allows this gifted chameleon both to spoof his own celebrity and offer another gentle caricature of misfit sensitivity, à la The Nutty Professor. Oz clowns on everything from the insidious influence of Scientology to the sexual quid pro quo driving so much casting without ever stooping to mean-spiritedness. That’s the joy of his farce: It looks at the cynical truth of Hollywood through widely innocent eyes, all while colliding the unexpectedly simpatico shtick of two comedy legends. —A.A.D.

Like every 007 before and after him, Pierce Brosnan has played a few debonair ladykillers outside of the tuxedo, too. A mere three months shy of reprising the role of James Bond in The World is Not Enough (see above), he unofficially refined it, deviously tweaking his preppy charisma to portray a suave art thief in this effortlessly stylish remake of a 1968 Steve McQueen caper. Rene Russo matches Brosnan step for step as the smart, sexy insurance investigator on his tail; the two dance wittily around their mutual attraction, before surrendering to it during the kind of steamy Hollywood love scene now as rare as an original Monet. Most actual Bond movies would kill for their chemistry — or for a scene as nimble and playful as the closing heist, which Die Hard director John McTiernan sets to the jaunty, timeless accompaniment of Nina Simone’s “Sinnerman.” —A.A.D.

The Nineties loved the aesthetics of the 1960s. (Remember that ever-present hippie smiley face?) But maybe no film did kitschy Sixties aesthetics better than Andrew Fleming’s delightful but also delicious political comedy. Kirsten Dunst and Michelle Williams are two goofy girls who accidentally stumble upon the Watergate break-in. They soon become persons of interest for both Richard Nixon himself (a perfect Dan Hedaya) and Woodward and Bernstein (Will Ferrell and Bruce McCulloch), all while maintaining their glorious cluelessness. Tricky Dick never stood a chance. —Esther Zuckerman

This love letter to indie-rock heroes Fugazi was a lot like the band’s music: uncompromising and intense, at times a bit tedious but ultimately uniquely rewarding. Dispensing with crutches like narration or contextual hand-holding, filmmaker Jem Cohen, a trusted friend of the band for years, deep-dives into a impressionistic blur of live and studio footage, as well as interviews with the band and their fans (including an adorable clip of singer-guitarists Ian McKaye and Guy Picciotto on a cable access show hosted by a teenage girl). The performance clips are often spellbinding, including an instantly legendary moment from a show in a high school gym where Picciotto sings suspended upside down from a basketball hoop. And the band’s unparalleled integrity and determination come through in every grainy, disjointed, process-obsessed, passion-filled minute. —J.D.

Anthony Hopkins isn’t the only stocky Brit with a deranged chef on his resume of Nineties roles. To his alphabetical right stands Cockney tough guy Bob Hoskins, who brings a rather subtle, subdued menace to this haunting thriller about an Irish teenager who goes looking for her lost love and instead falls into the clutches of a seemingly kindly cook with some dangerously unresolved mommy issues. Just don’t expect cheap serial-killer thrills — not with Atom Egoyan behind the camera and keyboard. The Exotica director fractures his William Trevor source material into another puzzle-box tragedy of childhood trauma, predatory men, and a past that keeps bleeding (via a trickle of flashbacks) into the present. The sound design — an overlapping din of voices, industrial noise, and staccato violin — suggests the room tone of a disturbed mind. But it’s the English bulldog in the lead who really opens a window into that space, letting us see the pitiable boy behind the madman. —A.A.D.

There’s a part of us that gets giddy at the idea that, having thrilled to Kate Winslet’s performance in Titanic, a gaggle of recently converted Winslet-ites then flocked to see this truly cracked psychodrama, about a young Australian woman who falls under the spell of a cultlike leader while in India. Once she’s eventually cajoled back to her hometown in Sydney, Winslet’s character is sequestered with an American (Harvey Keitel) who’s an expert in deprogramming brainwashed ex-cult members. Let’s just say that neither of them plans on giving up without a fight, and that the lines of what is and isn’t acceptable social behavior gets severely blurred in Jane Campion’s underrated take on spiritual voids and sexual power plays. Had Winslet’s previous movie not already been named Hideous Kinky, that title would have been equally appropriate here. —D.F.

Most tales of how we tamed the wild, wild West leave out some of the more grisly footnotes — luckily, director Antonia Bird’s berserk frontier-horror parable is more than happy to fill in the gaps. A traumatized army lieutenant (Guy Pearce) is transferred to a remote outpost in California after the Mexican-American War left him “unfit” for normal duty. He’s barely settled in with his fellow misfits and scallywags when a mysterious Scottish drifter (Robert Carlyle) shows up on their doorstep. It seems he was a member of a settlers’ party heading west through the Sierra Nevada, and after they became stranded without food for several weeks… let’s just say that desperate times begat desperate measures. The soldiers accompany him to the scene of the crime to rescue his fellow survivors, at which point they discover that both old habits and new appetites are hard to shake off. A singular mix of revisionist Western, stalker flick, survivalist thriller and, yes, even wackadoo comedy, Ravenous distinguished itself as one of the sickest jokes of 1999 — a reminder that America’s origin story includes cowards, cannibals, and good old-fashioned psychopaths. —D.F.