1999 Retrospective: The Best Films of 1999

W hat a remarkable year 1999 was. It was in a period long before streaming services, and virtually everyone went to the movies and the box-office wasn’t in draught. It was a year where brains and chances weren’t just taking place with indies and art-house films but also in studio films with Fight Club, The Insider, The Matrix, and The Talented Mr. Ripley. 1999 has unanimously been proclaimed a golden year for cinema, and rightfully so.  There is no denying that it was a remarkable year. To this date, there really hasn’t been a year since. It was as if the great auteurs from that year were in their rat race to complete their visions before the turn of the century. In return, so many films from that year went on to be greatly influential. In retrospect, there was a sense of optimism in filmmaking, but that has gotten lost with less risk-taking. While the film industry has opened the door for more diverse voices in the last 10 years, so many films aren’t given the proper spotlight due to oversaturation and less risk-taking from PR groups. So many films today struggle to turn a profit due to increased costs, labor shortages, and constraints, and so many have now turned to social media platforms and streaming services for their entertainment. Will we get another year, like 1999? That will remain uncertain. Even though we might have had some close ones since with 2002, 2003, 2011, and 2019 being the greatest, but in the meantime, at least we can always go back to that impressive year. The year was so great that I had to do 10 runners-up instead of my regular 5 or 6. Here is 1999’s finest:

Courtesy Dreamworks

1. American Beauty (d. Sam Mendes)

To see the shelf life of American Beauty evolve, dissolve, and now reluctantly resurface over the years has been interesting to observe. For starters, many like to use their own ethical standards and apply them to older movies, which, in my review, ends up making them feel self-righteous. Secondly, no audience should be excluded from feeling uncomfortable about movies. Film writers, directors, and artists should take creative liberties with complexities that make us feel uncomfortable. Just because a film explores certain inhibitions that might feel challenging and unethical doesn’t mean the storytellers condone them. Skillful Broadway director turned filmmaker Sam Mendes and screenwriter Alan Ball did just that with their remarkable feature film debut, American Beauty. A film I just revisited and still consider sophisticated, dark, moving, and honest—one of the best films from the 90s, and I still take American Beauty over any Best Picture winner of the 21st century, and we have had some great ones (Million Dollar Baby, No Country for Old Men, LORT: The Return of the King, Birdman, Parasite).

Kevin Spacey delivered an Oscar-winning performance as Lester Burnham, who writes for a magazine editorial and is a suburban father who is married to his real-estate saleswoman wife Carolyn (Annette Benning) and their teenage daughter Jane (Thora Birch). Lester is going through a mid-life crisis and feels detached from his mundane existence. He begins to feel youthful again after meeting Jane’s best friend, teen model Angela Hayes (Mena Suvar), and while many today believe that subplots are “creepy” or “dated” in part because of Spacey’s reputation, the subplot ends up being tasteful and holds a payoff. It also taps into some human desires, such as the yearning to feel young again, but Lester doesn’t act upon his lusts. Burnham’s suburban neighbors also include a gay couple next door, Jim and Jim (Scott Bakula and Sam Robards), and a new family that moved in with a conservative ex-Marine Colonel Frank Fitt (Chris Cooper). The Colonel is very strict with his son, Ricky (Wes Bentley), who works on the side selling marijuana, loves to document everything, and ends up falling for Jane. Ricky’s mother (Allison) is timid, light-spoken, and suffers from emotional trauma that was certainly created by the Colonel.

American Beauty was released just a year after Todd Solondz Happiness and the film echoes some familiar themes of David Lynch’s Blue Velvet in how it explores the facade of American suburbs. We follow Lester in the last few weeks of his life, and he narrates the film much like William Holden did in Sunset Boulevard. On his journey, we see Lester feel beaten down, confined, and lonely before finally breaking through his personal anguish. He quits his job, blackmails his boss with a nice severance package, buys a hot rod, smokes pot, confronts Carolyn about her materialism, works at a fast-food restaurant, and begins working out. He begins to recapture his spirit while his freedom impacts his marriage with Carolyn and relationship with Jane. The film is a bold work of art, which remains Mendes greatest accomplishment to date due to the great collaborations int he films. From Conrad Hall’s lush cinematography to Thomas Newman’s memorable score to both Spacey’s and Bening’s first-rate performances, American Beauty is a triumph of superb storytelling and filmmaking.

Courtesy Time Warner

2. Magnolia (d. Paul Thomas Anderson)

Reflecting back, it’s rather extraordinary how filmmaker Paul Thomas Anderson was only 29 years old upon the release of this third feature, Magnolia. Once I saw his third feature in the theater on a cold day in January of 2000, I knew, as a young high schooler at the time, that he was the real deal and a filmmaker that was going to have the talent of Martin Scorsese, Robert Altman, and Quentin Tarantino. Magnolia still remains Anderdon’s most ambitious film, and I would say it is easily his second finest, just after There Will Be Blood. From there, P.T. Anderson has maintained his reputation, and he has delivered so many great films since.  Sometimes it takes between 3 and 6 years for him to get a project launched. Anderson’s third favorite followed the energy and spirit of Robert Altman’s ensemble dramas, especially Short Cuts. Magnolia follows a group of characters in Anderdon’s frequent setting of his hometown of San Fernando Valley. The impressive ensemble includes Tom Cruise, Philip Baker Hall, Phillip Seymour Hoffman, William H. Macy, Julianne Moore, John C. Reilly, Jason Robards, and Melora Waters, who all turn in outstanding supporting performances of characters with deep emotional wounds, pathos, and vulnerabilities. Each of their subplots is interconnected, and every subplot is undeniably captivating.

The character that ties everyone together is Jason Robards, as Earl Partridge. An ailing man is living out his last days with cancer. His younger wife, Linda Partridge (Moore), confesses that she married Earl for his money, but now she genuinely loves him and doesn’t want anything from his will or estate. Hoffman plays Earl’s hospice nurse, who agrees to carry out Earl’s dying wish of tracking down his estranged son, Frank T.J. Mackey (Cruise), who is a misogynistic motivational speaker and author who trains men how to hold an advantage over women in their dating lives. Other stories include a child genius (Stanley Spector) who used to be a money maker on quiz shows for his father Rick (Michael Bowen). The quiz show is an Earl Patridge production, and it’s hosted by Jimmy Gator (Hall), who also just got diagnosed with cancer and feels ill. He also wants to reconnect with his estranged daughter Claudia (Walters), but she is tormented by her past and has a cocaine addiction. Claudia ends up having a romantic spark with a police officer named Jim Kurring (O’Reilly) during a police officer visit from a called-in disturbance. Finally, there is “Quiz Kid” Donnie Smith (Macy), who is a loner who is now broke after his parents cashed in his prize money, struggles to keep a job, and wants braces to impress his local bartender that he’s in love with. The scenes of all these characters are seamless with the accelerated and swift pacing that is executed so masterfully by Anderson. Of course, an event ties all the characters together with an unforgettable abstraction that feels biblical and metaphorical about bottled-up human emotions.

Anderson’s Magnolia has carried out a great legacy over the years as well. 25 years later, I would say Magnolia and Eyes Wide Shut probably remain the most timeless movies from 1999 for modern film critics and movie buffs. While I do have American Beauty slightly above Magnolia, there is no denying the artistry and impact this film has made over the years. It is a stone-cold masterpiece, one that is unique and impeccably written and crafted. A movie I have revisited so often and one that I will never get tired of watching again. The film’s score by Jon Brion, along with the selection of songs by Aimee Mann, also add to the dramatic momentum. There is one point in the film that has a musical number that works, where we see all the characters singing to the song. The performances across the board are great, and each of the supporting cast members could have easily earned an Oscar nomination because everyone pulls in such emotionally towering work here. Especially Tom Cruise, who is absolutely wrenching. Magnolia is a stunning and towering piece of cinema.

Courtesy Focus Features

3. Being John Malkovich (d. Spike Jonze)

1999 was a remarkable year for debuts, as we had The Bair Witch Project, Boys Don’t Cry, The Sixth Sense, and American Beauty. Being John Malkovich marked the debut feature of music video director Spike Jonze, who was already met with great acclaim for directing music videos by the Beastie Boys and Bjork. He also co-starred in David O. Russell’s Three Kings. Being John Malkovich also marked the screenwriting debut of Charlie Kaufman, who later went on to direct his own films with such titles as Synecdoche New York, Anomalisa, and I’m Thinking of Ending Things. Jonze and Kaufman proved to be a great collaborative duo by delivering a brilliant film that is both meta and personal. While Being John Malkovich features John Malkovich playing himself, he is a supporting character, and the film taps into an existential odyssey about the id, the subconscious, gender dysmorphia, human connection, celebrity status, mortality, and human loneliness. It’s a very original framework with shades of surrealism and dark comedy.

The film’s lead is about a detached puppeteer named Craig Schwartz (John Cusack), who can’t earn a living or a career with his puppeteering. He ends up getting a job as a filing clerk on the 7-1/2th floor of a reputable office building. While working, Craig ends up falling for his co-worker Maxine (Catherine Keener), but she doesn’t hold the same feelings for him. Craig eventually discovers a small door that ends up being a portal that leads into Malkovich’s mind. The portal allows Craig and anyone else to live in John Malkovich’s mind for some moments before being pushed out into the New Jersey turnpike. Craig and Maxine end up capitalizing on this unusual discovery and charging lonely people $200 a visit to be John Malkovich. Situations get disrupted once Craig’s wife Lotte (Cameron Diaz—nearly unrecognizable with frizzy hair and brown eyes), a kind-hearted pet shop owner and animal lover, ends up going into the portal, falls for Maxine, and discovers she loves feeling masculine. Malkovich, of course, plays himself, and there is a comical recurring gag in the film where people convince him that they saw him in a movie where he played a jewel thief.

It’s an audacious and equally inventive concept. Kaufman and Jonze prevent the film from slipping into self-parody on Malkovich, and the high concept never derails into a one-joke movie. The film continues to get more bizarre, amusing, and fascinating, and it’s always engaging. The film uses puppets as a metaphor that carries out Shakespear’s (who is referenced in the film) belief that the world is a stage and someone is always pulling the string. The puppetry by Phillip Huber is astonishing, and the film received three Oscar nominations at the time for Best Director (Spike Jonze), Best Original Screenplay (Charlie Kaufman), and Best Supporting Actress (Cameron Diaz), and it certainly deserved a Best Picture nomination. Years later, Being John Malkovich has held great shelf life, earning a Criterion spline and being considered a substantial masterpiece for both Jonze and Kaufman.

Courtesy Warner Bros.

4. Eyes Wide Shut (d. Stanley Kubrick)

It’s quite fascinating looking back at Stanley Kubrick’s filmography; so many of his films were polarizing to critics upon release. Years later, nearly each of his films has been reevaluated and is now widely celebrated by film critics and movie buffs today. I recall vividly being a teenager and hearing all the hoopla and divisiveness from critics and audiences. In fact, the audience I saw it in the summer of 1999 yelled out, “Worst movie ever!” which is a very knee-jerk reaction most have to any film that gives a hindsight of ambiguity. Years later, Eyes Wide Shut is now considered a masterpiece and continues to be celebrated today. That is because Kubrick films are enigmatic; they deserve to be revisited multiple times, and their brilliance only grows over time.

Like most of Kubrick’s films (2001: A Space Odyssey, A Clockwork Orange, Barry Lyndon), Eyes Wide Shut has an episodic structure. The odyssey here is a sexual one, involving Dr. Bill Hartford (Tom Cruise) and his wife, Alice (Nicole Kidman), who attend a Christmas party, and they both have some very flirtatious exchanges as they are going down different paths at the party. For Bill, he encounters two sexy female models who insist they go upstairs with him; for Alice, she dances with a very dashing middle-aged man, but they both hold back their desires. The following night, the couple discuss the evening as they smoke pot, and Alice suspects Bill went to bed with the two women when in fact he was ordered to by the host of the party (Syndey Pollock) after his fling overdoses on drugs. Alice ends up confessing a time she nearly cheated on him with a Navy office while they were on vacation. Bill ends up getting a call from the daughter of a patient, who informs him that his patient has died. From there, Bill finds himself having many bizarre, unsolicited sexual encounters throughout the evening.

Kubrick’s film unfolds like a dream, with many startling moments and sexual awakenings that further open up Bill’s desires. The irony is that Bill doesn’t end up having sex with anyone. Even though there are moments involving an encounter with a prostitute named Domino (Vinessa Shaw), he gets cold feet and doesn’t act upon it. He ends up going back to Domino the next day and is informed by Domino’s equally promiscuous roommate Sally (Fay Masterson) that Domino was just diagnosed with HIV and that he bit a bullet with that. Bill’s lust crosses a line after he pressures an old piano player friend Nick Nightingale (Todd Field), where they reconnected at the Christmas Party, and Nick informs him to attend a private sex party that he plays piano at. He gives him the password, and he picks up a mask, clock, and tuxedo in the late hours at the costume shop, where the owner (Rade Sherbedgia) discovers his flirtatious underage daughter half naked with two older men. During this exchange, Leelee Sobieski also comes onto Bill, and the night only gets more bizarre from there.

Kubrick, along with co-writer Frederick Raphael, end up upshifting the sexual odyssey into a murder mystery. When Bill’s disguise is revealed at the “orgy,” an unnamed woman with a mask spares him from facing consequences from crashing the party. The next morning, in a newspaper article, Bill reads of a young model that died from a drug overdose in her hotel room. Bill ends up becoming a makeshift sleuth; he goes to Nick Nightengale’s club, asks around what hotel he is staying at, and he finds out from the flirtatious desk manager (Alan Cumming) that Nick looks assaulted and was dragged out by strongmen. From there, the mystery gets more bizarre, and Bill’s inquiries become a crux as he is followed and begins to receive threats.

Thematically and technically, Eyes Wide Shut is a fascinating experience. The craft is undeniably artful, with Kubrick’s meticulous compositions, blue lighting, and impressive long takes and blocking loves to hover its silences and striking images. It’s a film rich in theme, texture, and artistry. Kubrick keeps the story flowing, and it has a dreamlike effect that moves in hallucinatory waves. It’s a film where you always feel illusive forces it unravels, one that unravels with austere rumbles and mystery. Eyes Wide Shut is one of those rare films that you can never get tired of revisiting because you discover another ambiguous and fascinating layer on each revisit.

Courtesy Walt Disney

5. The Straight Story (d. David Lynch)

It’s quite an ironic and fitting title for surrealist filmmaker David Lynch, whose films are often anything but “straight stories,” but The Straight Story is up there with The Elephant Man as not only being the most straight-forward narrative of Lynch’s impressive career but also his most humane. Based on an extraordinary true story, The Straight Story is a portrait of a 73-year-old widow named Alvin Straight (Richard Farnsworth in his final role) as he travels across the plain states on a riding John Deere lawnmower to lower Wisconsin to visit his ailing and estranged brother (Harry Dean Stanton) once he finds out that he suffered from a stroke. Even though it’s Lynch’s lighthearted film, Lynch’s sensibilities in style and tone still give the endearing script by John Roach such a singular vision.

There are certainly some quirks that echo Twin Peaks in The Straight Story that include Sissy Spacek playing Alvin’s daughter, who has a speech impediment, and Alvin’s next-door neighbor enjoys sunbathing with pink snowballs. There is also a great scene involving Alvin bringing the cost down of a repair on his lawnmower by two twin brothers. Nothing is condescending, though, as the characters feel genuine enough not to fall into caricatures.

Alvin can no longer drive a car due to his bad hip, so he has to walk on two canes. He also has poor vision, but he is determined to visit his brother on his lawnmower, even if it only goes 5 miles per hour and takes nearly 6 weeks to get to his destination. Alvin encounters a lot of supportive townspeople along the way, even ones that offer to give him a ride to his destination, but Alvin is stubborn in his own sincere way. There are many other genuine encounters as well, including a beautifully rendered scene with a pregnant runaway who Alvin ends up convincing to go back home. There is also some thoughtful existentialism in the film about aging that echoes Bergman’s Wild Strawberries when Alvin shares the brutal truths of growing old. He shares with them that the worst part about getting old is remembering being once. A truly illuminating and luminous film, in part due to Lynch’s poetic eye, brings a somberness to the material that is undeniably affecting. The score by the late Angel Badalamenti is also a highlight, along with the ravishing cinematography by Freddie Francis.

The Straight Story is another film that has held great shelf life due to its artistry, performances, and craft. It’s truly a remarkable achievement, one that I hope more families will discover in the long run. It’s a film of wisdom and grace, one that ranks up there with Sunset Blvd, Tokyo Story, Wild Strawberries, Amour, Vortex, and About Schmidt as being one of the most substantial films about the sad realities of old age, and it’s a unique road movie where the road is certainly a metaphor of having to plow through the drudgeries of everyday life.

Courtesy Touchstone Pictures

6. Summer of Sam (d. Spike Lee)

Summer of Sam is another Spike Lee masterpiece from the 90s that has stood the course of time. A movie about the Son of Sam serial killer ends up being about many other things involving mob rule, the dangers of group think, and how humanity uses crises to scapegoat for their own mistakes. The excellent cast includes John Leguizamo as Vinny, a womanizing hairdresser who endlessly cheats on his faithful and loving wife, Dionna (Mira Sorvino). Adrien Brody plays Richie, Vinny’s best friend, who secretly works at a gay peep show at night and lives out his individualism as punk rock by day, and Jennifer Esposito plays his girlfriend Ruby, who supports Richie’s style and aspirations in becoming a punk rocker. This is one of Spike Lee’s most stylishly directed films. His staging, along with cinematographer Ellen Kuras, has the New York grit and visual energy of a Martin Scorsese film. It also features a brilliant long take of Vinny and Dionna walking into a nightclub that is just as bravura as anything you would see in Goodfellas and Boogie Nights. The film also has a superb supporting cast, including Michael Imperioli, Ben Gazzara, and Anthony LaPaglia, to name just a few.

Like P.T. Anderson’s Boogie Nights, the film offers a first-rate soundtrack that includes many pop and disco songs from that era. Ordinarily, movies about serial killers, like Zodiac, merely become about obsessions with murders and the killer, but Lee explores the madness communities exhibit when confronted with fear and hysteria. The songs capture the vivid energy of that era, and the songs feel transcended by their impacts. Take, for example, a highly scripted and acted scene that involves a brutally heated exchange between Vinny and Dionna arguing about their sexual frustrations and regrets after participating in an orgy at night club, as Abba’s Dancing Queen plays expertly in the background.

Like he often does, Lee also captures race relationships and prejudices in the movie. Lee plays a TV reporter who interviews the black community and makes the great point that if the Son of Sam was a black man, there would be riots in the street and more hostility from New York white citizens. Lee taps into other prejudices and repressions with his characters as well. Richie is suspected by his neighbors of possibly being the killer because he wears a mohawk. Vinny holds a lot of sexual frustrations and is left unfulfilled because he fails to live out his desires with Dionna due to this Catholic guilt, and we see mob rule taken in effect by Michael Imperioli and Ben Gazzara, who leave them protecting their neighborhood and trusting nobody. Lee brilliantly examines how fear leads to fascist tendencies. In the 90s, Spike Lee was at a great peak, with such titles as Jungle Fever, Malcolm X, He Got Game, and Summer of Sam being great indications of his growth as a storyteller and craftsmanship. It will always remain a highlight and one of the most fascinating entries in his astounding filmography.

Courtesy Janus Films

7. Rosetta (d. Jean-Pierre Dardenne and Luc Dardenne)

1999 was the year the Dardennes started reaching acclaim within North American audiences after winning the prestigious Palme d’Or for their greatest accomplishment yet with Rosetta. Ever since their debut feature, La Promesse (1997), the Dardennes have continued to make films with a strong social realist style and parable themes. The handheld camerawork echoes the work of Dogme 95, which adds to the realist style, and the Dardennes shoot mostly with a 35mm lens, and they stage their dram with mostly tighter shots in their Belgium set.

The Dardenne’s heartbreaking film is about 17-year-old Rosetta (Emile Dequeene), who lives in a trailer on a caravan park just outside the city with her alcoholic mother (Anne Yernaux), who spends all of their money on booze that she shares with other residents on the campground. This leads Rosetta to find work so she can afford water and other utilities. She ends up getting a job at a local bakery owned by Olivier Gourmet, where one of his employees, Riquet (Fabrizio), who runs a waffle stand with his waffle mix, ends up taking an interest in Rosetta, but she has menstrual cramps that prevent her from enjoying the Riquet attraction. Meanwhile, Rosetta ends up losing her job at the bakery after the boss replaces her with his son. Out of money and desperate, she struggles to find work. Riquet ends up offering a job at the waffle truck, but she ends up discovering that Riquet is stealing batter from the bakery and selling his own waffles at a different cost. Rosetta ends up telling the owner in hopes she can start working the waffle truck. Of course, this creates further tension between Rosetta and Riquet, as Riquet feels betrayed, and Rosetta is sure enough to be given the apron to work the stand now.

The Dardennes take a very heartbreaking story about human struggle, and they make the human drama undeniably intricate. The riveting performance by Émilie Dequenne deserves a lot of credit. She was only 17 years old at the time, and it was her debut role. The performance was one of the most emotionally charged teenage performances I ever saw. The Dardennes never tug at your heartstrings; they don’t even use a score, and they avoid cliches. The performance is honest, and the Dardennes bring a lot of emotional vulnerabilities to the character and material. Rosetta is a home-grown Belgian drama that makes no compromises with its emotional truths, humanism, and realism.

Courtesy Touchstone

8. The Insider (d. Michael Mann)

Michael Mann’s most mature film, The Insider chronicles the story of a whistle-blower who went to CBS’s reputable TV show 60 Minutes about the unethical businesses of the tobacco company Brown and Williamson, the whistle-blower is Jeffrey Wigand and its played superbly by Russell Crowe in a career-defining performance. Jeffrey was recently released under a severance from Brown and Williamson once he finds out some damaging evidence on the harms of nicotine. Choosing between protecting his career, livelihood, and the well-being of his family–Jeffrey in good faith feels bad about taking severance money as it feels like blood money. He downsizes his lifestyle, moves his family into a smaller home, and takes a chemistry teaching job at a local middle school. His confident is 60 Minutes producer Lowell Bergman (Al Pacino) as both men must build up their trust as Jeffrey is caught in a web of anxiety, uncertainty, distrust and paranoia. Mann’s drama unfolds with one engrossing scene after the other, the effect is gripping.

The Insider is every bit as taut as any thriller you would see–but the suspense unravels with cell phones, backroom conversation, in hotel bars, and private dining rooms inside sushi bars instead of shootouts and chase scenes. Mann’s tone and execution showcases his directing brilliance, and it’s riveting seeing these characters evolve throughout the story. Mann’s film is also a cautionary tale in how journalism with 60 Minutes was one of the last resources for journalism with integrity before it got co-opted by corporations. The Insider is an expertly crafted, taut and one that hold the vision and scope of 1970s issue-driven films, and every bit as intricate and intriguing.

Courtesy Sony Pictures Classics

9. American Movie (d. Chris Smith)

A towering tribute to independent filmmaking and to the persistence, agony, and suffering that go into it, American Movie is one of the greatest documentaries ever made about the filmmaking process. Very much like a MidWest version of Ed Wood, Chris Smith’s compelling documentary is about Mark Borchardt, an indie filmmaker from Wisconsin who holds deep passion and a great vision for horror filmmaking. He even has a business plan for his latest short film, Coven (pronounced by Borchardt as Coe-ven). He plans on selling 3000 VHS tapes at $15,00 a piece plus ticket sales from the premiere, and Borchardt can pay back his irritable and cynical 82-year-old Uncle Bill’s money after he makes an investment with his savings.

Borchardt’s passion and drive are both quirky and sad; he clearly has a deep love for filmmaking, but you can see his filmmaking jeopardizing his job and relationships, and it takes away from his role as a father. Borchardt also works with a very bare-minimum crew, which often only consists of him and his best friend, Maike Schank, who is Mark’s right-hand man in sound, camera, and just about any other position that needs to be filled. Borchardt also has his own demons; as you can see, he had a breakdown after getting drunk during a Super Bowl game. On the surface, American Movie could feel like a Christopher Guest mockumentary, but it’s real and every bit as inspiring, amusing, and involving.

Courtesy Paramount Pictures

10. Election (d. Alexander Payne)

Election, Alexander Payne’s sophomore film, strays into the teenage comedy genre, casting Matthew Broderick and Reese Witherspoon in some of their most impressive and darkest comedic roles yet. At the film’s center is Jim McAllister (Broderick), a high school government teacher who becomes rivals with his overachiever student Tracy Flick (Witherspoon). As Tracy runs for student body president, Jim holds some resentment towards her after she had a sexual relationship with his colleague and best friend, fellow geometry teacher Dave Novotny (Mark Harelik). While Jim feels Dave deserves to face consequences for his actions, he feels Tracy is a self-serving opportunist. Through this, McAllister ends up convincing Paul (Chris Klein), a simpleminded but popular student athlete, to challenge Tracy. Jim also gives pointers so Paul can gain more votes to defeat Tracy, and this escalates the tension between them.

Their situations gain more friction when Jim does other unethical things to sabotage Tracy’s election campaign, even if it means throwing away a few votes from Tracy during the recounts. Election is similar in satire to Citizen Ruth, which was also about fellow Nebraskan residents doing vicious things towards one another for their own personal gain. The tone of this film is even darker in humor than all of other Payne’s films, which likely explains how well it picked up a cult-following and eventually a spine in the Criterion Collection.

Election was the second time Payne was in the director’s chair too, and you can already see the growth in his writing and directing style. For that reason, it’s often thought of as the earlier film before Sideways. It ended up being the first adaptation by Payne and second of six features he co-wrote with fellow screenwriter Jim Taylor. The movie remains one of Payne’s sharpest and most sophisticated films and is found on many critics’ top 10 best of the year lists for 1999.

Read my Alexander Payne full article on Film Obsessive at A Toast to Complexity and Poignancy: Alexander Payne’s Films, Ranked | Film Obsessive 

Runners-Up (In Alphabetical Order)

All About My Mother (d. Pedro Almodóvar)

Easily one of Pedro Almodovar’s most remarkable films, All About My Mother was a highlight in his filmography and in 1999 cinema. The story of a mother who tragically loses her son after getting hit in a car accident travels out to Barcelona to find her son’s father, who now identifies as a transgender woman. Almodovar always works best with his Douglas Sirk and Tennessee Williams inspirations, and he utilizes his inspirations to explore very complex human issues such as motherhood, faith, gender identity, and existentialism.

Autumn Tale (d. Eric Rohmer)

The late and great Eric Rohmer was 90 years old when he directed this dramatic romantic comedy that is both sophisticated and witty. It was also the final film in his “Tales of the Four Seasons” series. I watched the film 25 years later, and it still resonates today. It has the formula of a Hollwood romantic comedy with its love triangle, but it is smarter, more refreshing, and unfolds without contrivances and with spontaneity and visual splendor.

Boys Don’t Cry (d. Kimberly Pierce)

Kimberly Pierce’s stunning debut feature, Boys Don’t Cry, would probably be politized and more controversial today. It’s a true story about a young female-to-male transgender man named Brandon Teena (Hilary Swank) who drifts into a small town and falls in love with Lana (Chloë Sevigny), an aspiring singer, and their love blossoms together the more they get to know each other. Sadly, their romance is disrupted after Lana’s ex-convict friends, John (Peter Sarsgaard) and Tom (Brendan Sexton III), discover Brandon’s trans identity, and hostility and tragedy follow. Both fulfilling and heartbreaking, Boys Don’t Cry remains an essential piece.

Courtesy Touchstone

Bringing Out the Dead (d. Martin Scorsese)

Before he entered a level of self-parody, there was a point in the 1990s when Nicolas Cage was considered one of the greatest actors working in Hollywood. Fresh off his Oscar win for Mike Figgis’ Leaving Las Vegas, Nicolas Cage was yearning for another complex character role. While he didn’t get an Oscar nomination for his first and only collaboration with Scorsese, Bringing Out the Dead is easily one of Cage’s top five best performances of his career. He brings a melancholic intensity to the film, which chronicles a few days in the life of an insomniac ambulance driver who is tormented by regret and visions of an 18-year-old girl that he failed to save. The screenplay by Paul Schrader works as a companion piece to his and Scorsese’s earlier masterpiece Taxi Driver and also shows the moral decay still eating away at the core of New York City’s citizens.

Cookie’s Fortune (d. Robert Altman)

The late Robert Altman’s hilariously witty film is the flip side of P.T. Anderson’s Short Cuts inspired Magnolia, telling the story of a Mississippi community living in the aftermath of a tragedy after an elderly widow named Cookie (Patricia Neal) takes her own life, and her daughter Camille (Glenn Close) covers up the suicide once Cookie learns she left a will to her handyman named Willis (Charles S. Dutton), who the entire community and local sheriff (Ned Beatty) know that Willis would never commit such a crime. While Cookie’s Fortune never quite reached the acclaim of Short Cuts, The Player, or MASH, Cookie’s Fortune is one of Altman’s most charming and enjoyable gems that deserves more praise in part for its colorful characters, terrific ensemble cast (Charles S. Dutton and Julianne Moore are standouts), impeccable visual style, and kindred spirit.

Fight Club (d. David Fincher)

Fight Club has had many different followings over the years–ranging from emo, hipsters, goth, and even to frat boys and tragically right-wing alt-right libertarians who identify with the films toxic masculinity and pervert and misunderstanding of the themes. “Fight Club” remains a signature cult film today, but recently it has received some backlash for it being dated with its toxic masculinity approach, and the endlessly annoying fanboy reaction has damaged the film’s reputation over the years. Pulpy and lurid, it can be a little wearying at times, but nevertheless, the film is highly unique and compulsively watchable due to some memorable set-pieces and scenes (such as the infamous basement fight and the “twist” ending involving Edward Norton and Brad Pitt as the ending that recalls the tragedy of 9/11), “Fight Club” should remain and be appreciated for a product of its time, an era where filmmakers made bold and innovative choices, both thematically and stylistically, and Fincher managed to do this with his most cult-driven movie to date.

The Limey (d. Steven Soderberg)

Immediately after the critical and commercial success of Out of Sight, Soderbergh dived right back into more indie routes that proved Soderbergh is a master at the crime genre. The Limey is steeped in movie references, a neo-noir thriller intertwined as a revenge saga that has a richly moody atmosphere that echoes the work of Michael Mann, Ridley Scott, William Friedkin, and Dog Siegal-who also created revenge films about tough, stoic men embarking on revenge-but Soderbergh still allows the material to feel fresh and live thanks mainly his unique editing style and playful structure. The Limey is truly a visually sublime piece of filmmaking.

The Matrix (d. Lana Wachowski and Lilly Wachowski)

Though Lana and Lily Wachowski made a monumental splash with their 1996 neo-noir thriller Bound, it was just a demo for their commercial masterwork The Matrix, which undeniably left a monumental imprint on film history with its extraordinary action sequences and philosophical ideas. Even though The Matrix saw success in spring with a modest box-office opening, it grew week after week with its word-of-mouth and eventually became a commercial success with inferior sequels. Keanu Reeves was perfectly cast as Neo, an ordinary office worker who breaks out of his confined reality of the mundane and joins forces with a group of underworld rebels to combat against a band of secret agents that want to maintain humanity in the artificial world. The Wachowskis deliver enthralling action sequences while staying visionary on their themes of free will and the perceived world at the same time.

Princess Mononoke (d. Hayao Miyazaki)

For the record, I have always considered Princess Mononoke to be Hayao Miyazaki’s greatest accomplishment. For starters, it’s his most artful, ingenious, and enthralling work that has many profound things to say about humanity’s hostile actions towards nature that causes ecological consequences. The older I get and as climate change intensifies, the message hits even harder. Happily, Miyazaki films age very well due to his uncanny vision, wonderous storytelling, and breathtaking animation. Miyazaki captures a peculiar magic in Princess Mononoke that will forever remain extraordinary.

Run Lola Run (d. Tom Tykwer)

Tom Tykwer’s Run Lola Run is one of the most energetic films you will ever see. With a running time of 80 mins, that shifts between many styles of animation, HD, and film, all these years later Tykwer’s film remains an extraordinary feat. It’s not all style over substance though, as the film offers some humanistic touches about relationships, love, and family with its brisk pacing. The film is about Lola (Franka Potente) who unwinds time to undo the dangerous fate that awaits her from one bad decision. It’s a stylistically rich film, one that has aged very well over time with its brilliant editing and swift style.

Three Kings (d. David O. Russell)

David O. Russell’s greatest accomplishment, a potent satire on American interventionism in Iraq, Three Kings, is scripted in a sophisticated way that feels vivid and timeless. With its setting in the Iraq War, the film tells the story of four American soldiers (George Clooney, Ice Cube, Mark Wahlberg, and Spike Jonze) who find themselves involved in a gold heist during the 1991 uprisings against Sudam Huissen. O. Russell deconstructs the war genre and builds up a satirical and equally harrowing lament for humanism, moral courage, and, while we’re at it, hope in foreign relations.

Honorable Mention (In Alphabetical Order)

American Pie (d. Paul Weitz)
The Dreamlife of Angels (d. Eric Zonca)
The Green Mile (d. Frank Darabont)
Man on the Moon (d. Milos Foreman)
The Iron Giant (d. Brad Bird)
The Sixth Sense (d. M. Night Shyamalan)
The Talented Mr. Ripley (d. Anthony Minghella)
Titus (d. Julie Taymor)
Topsy Turvy (d. Mike Leigh)
Toy Story 2 (d. John Lasseter)
The War Zone (d. Tim Roth)

Don’t Worry!! The Audition, Beau Travail, Ghost Dog: Way of the Samurai, Ratcatcher, and The Virgin Suicides are included in the 2000 Top 10 list due to the North American Theatrical Release Date.