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by Jason Frank Koenigsberg

The headline says it all. 1999 was a game changer for cinema. One could argue that it was the greatest year for movies in the history of the art form. From movies as big and special effects-laden as The Matrix, and Star Wars Episode I: The Phantom Menace, to smaller almost minimalist efforts like The Blair Witch Project, and Run Lola Run, that have proven to be every bit as influential as the big titles. Even the animated movies from that year were outstanding and incredibly diverse ranging from Toy Story 2, to The Iron Giant, to South Park: Bigger Longer, and Uncut. 1999 was a very special year for movies.

1999 brought us Eyes Wide Shut, the final film from Stanley Kubrick, but 1999 also featured a murderers row of great directors having their films released. From Sidney Lumet (Gloria), Martin Scorsese (Bringing Out the Dead), Rob Reiner (The Story of Us), Anthony Minghella (The Talented Mr. Ripley), Alan Parker (Angela’s Ashes), George Lucas (Star Wars Episode I: The Phantom Menace), Tim Burton (Sleepy Hollow), Lawrence Kasdan (Mumford), Milos Forman (Man on the Moon), Oliver Stone (Any Given Sunday), Hayao Miyazaki (Princess Mononoke), Kevin Smith (Dogma), Woody Allen (Sweet and Lowdown), Barry Levinson (Liberty Heights), Norman Jewison (The Hurricane), Pedro Almodovar (All About My Mother), Steven Soderbergh (The Limey), John MacTiernan (The Thomas Crown Affair and The Thirteenth Warrior), Garry Marshall (The Other Sister and Runaway Bride), Chris Columbus (Bicentennial Man), Clint Eastwood (True Crime), Mike Judge (Office Space), Sydney Pollack (Random Hearts), Sam Raimi (For the Love of the Game), Harold Ramis (Analyze This), Ang Lee (Ride with the Devil), Lasse Halstrom (The Cider House Rules), Frank Darabont (The Green Mile), Michael Mann (The Insider), and Ron Howard (EdTV), to David Fincher (Fight Club), David Lynch (The Straight Story), David Cronenberg (eXistenZ), Spike Lee (Summer of Sam), and Mike Leigh (Topsy Turvy). It also saw the formal arrival of new voices in cinema. Directors that would go on to become important filmmakers of the twenty-first century such as Spike Jonze (Being John Malkovich), David O. Russell (Three Kings), Paul Thomas Anderson (Magnolia), Sam Mendes (American Beauty), Alexander Payne (Election), Tom Tykwer (Run Lola Run), Doug Liman (Go), M. Night Shymalan (The Sixth Sense), and The Wachowski siblings (The Matrix). A lot has been written about 1999 as a landmark year in cinema and many point to the Academy Awards as one of the worst in years considering what they chose to nominate and what actually won. The Oscar nominees from that year in no way represent the best in film from 1999 and are a poor way to gauge the monumental cinematic achievements released that year. American Beauty and The Cider House Rules were the two front runners with the most nominations. However, on the plus side, The Matrix did win all of the Oscars it was nominated in going four for four and nobody probably saw that coming. 

So let’s take a look back at the best films of 1999. Some are from prolific directors further establishing their reputations for uncompromising greatness, some are from rising stars that have continued to reshape movies with their visions, but all are outstanding works that still hold up twenty years later. 

20. Summer of Sam (directed by Spike Lee)

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Spike Lee made a lot of terrific movies throughout the 90’s but he ended the decade particularly strong with the trio of powerful films Four Little Girls (1997), He Got Game (1998), and Summer of Sam. His final film of the 90’s was kind of similar to his breakout hit and final film of the 80’s Do The Right Thing (1989). Both movies involve a New York City neighborhood gripped in fear and paranoia during a swelteringly hot summer. You can feel the sweat dripping down the characters faces and the heat permeate off the screen. Both neighborhoods are feeling the heat and are driven to making extreme decisions. Summer of Sam takes place during the record hot summer of 1977 when the Son of Sam killer stalked New York City killing brunette women. Spike Lee recaptures the mayhem and pandemonium with the killer stalking these characters in the background and their personal problems elevated by the news in the foreground. It even features Jimmy Breslin, the detective who cracked the case and arrested David ‘Son of Sam’ Berkowitz. The film was met with scathing reviews mixed in with some four star commendations including one from Roger Ebert. It died at the box office in early July during the blockbuster season, a curious release date to say the least for such a violent and sexually charged picture. Like many of Spike Lee’s films of this era, Summer of Sam is a great underrated movie. 


19. Any Given Sunday (directed by Oliver Stone)


The most earthshaking powerhouse movie ever made about football is Oliver Stone’s Any Given Sunday. Today it is most well known for being the breakout role for Jamie Foxx and his gateway to more serious Oscar winning roles. Prior to this he was only known as a comedian and comic actor in films like The Great White Hype (1996) and Booty Call (1997). Oliver Stone unlocked his potential as he shared scenes opposite Al Pacino and the rest of the world took notice. However Jamie Foxx’s legacy overshadows the legacy of the film as a whole. Any Given Sunday is one of the best football movies ever made (there have not been a lot) as well as the last great film directed by Oliver Stone. It is also the last great film performance from Al Pacino. Plus Any Given Sunday features terrific supporting turns from Cameron Diaz and James Woods. All of those legendary actors are overlooked by Jamie Foxx and the good but not great reviews were not enough to make it an Oscar contender in December of 1999.

18. Mumford (directed by Lawrence Kasdan)


From two underrated movies to arguably the most underrated movie of all time, Mumford died a quick dead at the box office in the fall of 1999 and probably due to its lack of stars in the film going up against pictures like American Beauty, Double Jeopardy, and Three Kings. But there is no lack of talent in this cast that is for sure. Mumford is about a therapist who is not really who he says he is, but it is also one of the few movies that is guaranteed to make you feel better after you watch it. Kind of like therapy should. Despite the fact there were no big stars in the cast, Mumford has terrific performances from talented actors such as Loren Dean as the title character, along with the always reliable Alfre Woodard, Jason Lee, Hope Davis, Martin Short, and a young Zooey Deschanel just to name a few. One of the most delightful comedies from one of the best years for movies. 

17. Sleepy Hollow (directed by Tim Burton)


Tim Burton was on a hot streak in the 90’s. Actually from the mid-80’s until the mid-90’s one could argue Tim Burton never made a bad movie. Then came Mars Attacks! (1996) which I actually liked but was a critical and commercial failure. He needed to rebound and in a big way. So he made the most Tim Burton-esque movie of his career with Sleepy Hollow. A brilliant reimagining of the Washington Irving classic, while also being a loving homage to the Hammer horror films from England which were a huge influence on Burton. Inspired casting of Hollywood heartthrob Johnny Depp as Ichabod Crane opposite Christina Ricci. Leave it to Tim Burton to romantically link Edward Scissorhands with Wednesday Addams. Practically every frame in Sleepy Hollow is like a work of art that could hang on a wall. A gorgeous gothic horror film and Tim Burton’s last great movie. 

16. Bringing Out the Dead (directed by Martin Scorsese)

Another extremely underrated film and the last time Scorsese was ever working as a struggling director. Before Scorsese was regarded as a national treasure and making big budget award winning blockbusters with Leonardo DiCaprio he was a visionary director that few producers wanted to fund to realize his visions. This movie, like Taxi Driver is Scorsese at his most relentless and passionate. It is an uncensored look at a man dealing with moral, ethical and religious questions, all of which are themes that run through every Scorsese film. Bringing Out the Dead is a fiery and visceral movie. Scorsese’s direction is as energetic as always. Nicolas Cage gives an inspired performance worthy of a Best Actor Academy Award nomination as Frank the ambulance driver and paramedic who has worked the graveyard shift too long and feels he is cursed. This is the forgotten Scorsese masterpiece and the end of an era when Scorsese movies came and went from theaters unappreciated by the masses. 

15. The Matrix (directed by The Wachowskis)


The movie from 1999 that created a cultural phenomenon did take heavily from science-fiction and action movies most recognizably Blade and Dark City from the previous year. But none had the impact of The Matrix combining kung fu martial arts with computer savvy techno thriller elements and creating a philosophy reminiscent of Plato that would be taught in college courses the semester after The Matrix was released. This plot was nothing new, but the way this movie connected with audiences was incredible. One of the most highly influential movies of its time, after The Matrix, all action movies stopped looking like Die Hard (1988) clones and more like Matrix clones. The Matrix ended up winning four Academy Awards on a night that was predominantly about awarding films that could have been made any other year, or decade for that matter, was a real coupe for the blockbuster. Wrongly accused of influencing the mass shooting at Columbine High School in April of 1999, The Matrix was arguably the biggest event movie of the year taking away from George Lucas and the underwhelming response to Star Wars Episode I: The Phantom Menace. Today with Keanu Reeves having a career resurgence, people are forgetting about the lackluster response to The Matrix sequels and remembering this movie as a modern classic on its twentieth anniversary. A stylistic landmark in cinema. 

14. Bowfinger (directed by Frank Oz)


1999 was a landmark year with a lot of last’s. The last time Scorsese struggled, the last great Oliver Stone movie, the last great performances from Robert De Niro and Al Pacino, and also the last great performances from comedy legends Steve Martin and Eddie Murphy, starring in a movie together for the first time with the hilarious Bowfinger. Released in August of 1999, a week after The Sixth Sense which turned out to be the biggest surprise hit of the summer and year for that matter, Bowfinger despite outstanding reviews, faded relatively quickly in theaters. By the time fall came around nobody even remembered this movie existed. What a shame. Bowfinger is not only a hilarious comedy and one of the best films from its two iconic stars, but is one of the best movies about filmmaking that has ever been released. It captures the idiosyncrasies of Los Angeles better than most other films. Bowfinger is a look at the show business culture from the struggling actor and filmmaker’s point of view. A very heartfelt story despite its criticism of the Hollywood system and its players. 

13. The Straight Story (directed by David Lynch)


Always willing to challenge himself as an artist and seldom taking the same route twice David Lynch followed up his skewed, violent, sexual mystery Lost Highway with a G-rated Disney movie. That is right, David Lynch made a family movie for Walt Disney Pictures. But this is not just a curio or an experiment to watch once and then disregard. The Straight Story is Lynch’s most sincere, compassionate and subtle movie about the importance of family and the strong bond between brothers. Based on the incredible true story of Alvin Straight who took his John Deere lawnmower on a 200 plus mile journey across several states in the Midwest to see his brother after he found out he had a stroke. Even though it does not have the violence, profanity and sexuality that have become staples of a David Lynch film, The Straight Story feels very much like a David Lynch film. It has the same themes of a strong central character against all odds, going on a journey that ends up being a journey of self-discovery and he meets some very quirky misfit characters along the way. This movie is so subtle that a lot of people may complain that nothing happens in it for two hours, but the end is so powerful that once you reach the peak with Alvin Straight you realize that so much has happened during his voyage across America’s heartland. It is an eloquent look at American life and features a strong performance from its lead actor Richard Farnsworth as Alvin Straight. The Straight Story would be his final acting role and he earned a well deserved Best Actor Oscar Nomination for it. The film barely made a dent at the box office which is probably why it was only nominated for one Academy Award. All of Lynch’s signature auteur brush strokes are available in a mild and less hyper-stylized manner. I would love to see other great filmmakers like Quentin Tarantino, Oliver Stone and Paul Thomas Anderson leave their signature R-rated comfort zones and challenge themselves to create a beautiful and artistic film that can universally entertain, educate and transport audiences as well as still feel very much like a film that belongs next to their greatest masterworks. The Straight Story is the one great David Lynch movie for people of all ages and is a film that should be cherished as his most unexpectedly powerful film.

12. Eyes Wide Shut (directed by Stanley Kubrick)

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Stanley Kubrick’s final haunting masterpiece was not quite met with the resounding praise expected upon its initial release during the crowded summer of 1999. A soft number one at the box office the week after American Pie was released, and two weeks after South Park: Bigger, Longer, and Uncut. All three films dealt with sex, but in completely different ways, and all three challenged the MPAA and were threatened with the dreaded NC-17 rating. Eyes Wide Shut ended up grossing the least of those films despite having the star power of real life husband and wife Tom Cruise and Nicole Kidman. This is one of the most mature surreal sexual fantasies. Perhaps because of its 159 minute run time which would have meant the best option to avoid the heat for the longest amount of time, audiences were reluctant to see it. Eyes Wide Shut like most of Kubrick’s films was misunderstood on its initial release but like all of his work, it has only grown in reputation as a classic in the twenty years since. Possibly the best allegory about the futility of marriage and the fragility of all relationships. Plus Eyes Wide Shut was ahead of its time with regards to how it hinted at the Knights Templar and a secret society of powerful, wealthy people having orgies and controlling various aspects of common people’s lives. Dan Brown’s ‘The DaVinci Code’ touched on these themes more blatantly pushing them into the public consciousness. Critics lavished Nicole Kidman for a brutally honest performance that boils down to one major monologue which was the turning point of the film setting Tom Cruise on a surreal sexual odyssey to find the truth and get revenge on his wife. Cruise’s performance was the one that carried the movie and deserved to be celebrated because the audience was on the journey with him, seeing everything through his eyes and experiencing lust and betrayal. The colors and cinematography looked as though they only could have been shot by Kubrick. Even if this was released during the more typical awards season of November and December Eyes Wide Shut would have likely received the same tepid response. Twenty years later it joins Kubrick’s other works as fine wine that has aged gracefully with time. 

11. The Limey (directed by Steven Soderbergh)


Steven Soderbergh was in the middle of a hot streak with Out of Sight (1998) when he made The Limey, and followed that up with the three biggest hits of his career Erin Brockovich, Traffic (both made in 2000), and then Ocean’s Eleven (2001). The Limey was the least conventional and least successful of those films but it remains one of the most unique revenge thrillers of all time and the crowning achievement of Terrence Stamp’s career. The editing that jumps decades back and forth in a matter of seconds could make The Limey a jarring experience but provides insight into the main character with one thing on his mind, finding the truth about his daughter. The old cockney gent strolling around modern day L.A. makes The Limey a great fish out of water tale as well. Released limited in the fall of 1999 it was overlooked by a crowded release schedule and never expanded beyond major cities, The Limey has found an audience and is cherished by some but not as many as it could have been. To date this remains my favorite film from Steven Soderbergh who is always willing to experiment and try something new. He had never made a movie like The Limey and there will likely never be another film like it in the history of cinema. 

10. Boys Don’t Cry (directed by Kimberly Peirce)

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Now we have arrived at the top ten which is the same top ten I made back at the tail end of 1999/early 2000. Rather than change the order of these films to accommodate more timely taste I’d like to reflect on why these films were the ones chosen to be the best of the year. Boys Don’t Cry made the cut because of the outstanding gender-bending performance from Hilary Swank as Brandon Teena/Teena Brandon navigating her way through life and love as a transgender person in rural Nebraska. Based on the tragic true story there was no better performance in 1999 than Hilary Swank who deservedly won the Best Actress Academy Award. Saying this is the best performance of the year is saying a lot and even though Boys Don’t Cry is a particularly difficult film to watch and even harder to re-watch, it deserves all of of its merits and then some. Career best work from Chloe Sevigny who earned a Best Supporting Actress nomination and the best film from then groundbreaking director Kimberly Peirce before it became fashionable to hire female directors and give their films the awards season push. It was on more top ten lists in 1999 than almost any other film and remains a powerful movie of a tragic story about how homophobia in middle America has ruined lives. 

9. Analyze This (directed by Harold Ramis)

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So many serious great films came out in 1999 but also some of the funniest comedies. Not as original and irreverent as some other comedic films from the year but I for one honestly laughed out loud more during Analyze This than any other movie that year. That has to count for something and that is why it made it onto my Best of the Year list. De Niro is great spoofing his Mafia tough guy image, Billy Crystal is great as the nebbish psychiatrist trying to help the ailing mobster with his work and family issues, and Lisa Kudrow is annoying but was the flavor of the month and this is her best movie role. The scenes between De Niro and Crystal are hilarious banter and because of the massive success of Meet the Parents (2000) and HBO’s The Sopranos around the same time, along with the terrible sequel Analyze That (2002), the greatness of Analyze This has been mostly forgotten over the past twenty years. It was one of the last great De Niro performances when that phrase was more commonplace and not an anomaly. Analyze This was a big box office hit in early March before The Matrix dominated the box office at the end of March. In between was a lot of teen movies like Cruel Intentions and 10 Things I Hate About You, but Analyze This was one of the few adult oriented comedies that found success in early 1999.

8. The Green Mile (directed by Frank Darabont)


Back when Tom Hanks was a perennial Oscar favorite The Green Mile was Frank Darabont’s long awaited follow-up to his sleeper hit The Shawshank Redemption (1994). This was a more typical Oscar bait picture despite that it was based on a Stephen King tale with supernatural elements. With a running time over three hours The Green Mile had an epic Oscar caliber feel. And what is wrong with that? It is a spectacular and emotionally moving experience, but in the year of 1999, it did not feel wholly original, in fact this movie could have been made with a similar cast and special effects almost anytime during the 1990’s. It is a beautiful film with terrific performances from Tom Hanks and Michael Clarke Duncan in an Oscar nominated role. Even Sam Rockwell who was an up and coming actor was easy to hate in a villainous role. He had a terrific December of 1999 with The Green Mile and Galaxy Quest both being released a few weeks apart. The Green Mile deserved a lot of the love it received at the time and holds up very well today despite being a little bit long winded. 

7. Topsy Turvy (directed by Mike Leigh)


The best British production of 1999 and the best and liveliest film from writer/director Mike Leigh who usually specializes in working class dramas, comes a two hour and forty minute light hearted comedy about the minds and egos and clashes of Gilbert and Sullivan while they were making their opera ‘The Mikado’. Topsy Turvy is a masterpiece of the highest order with some of the best music, sets, and costume design from any film in 1999. Sadly, this was a year of American visionary films taking center stage and Topsy Turvy had to take a back seat to more avant-garde pictures that crossed over into the mainstream that year. Had it been produced by Weinstein’s Miramax and had their expensive campaign behind it, or been released practically any other year Topsy Turvy would have cleaned up more at the Academy Awards and made more money at the US box office.

6. The Talented Mr. Ripley (directed by Anthony Minghella)


When I first saw The Talented Mr. Ripley in theaters I hailed it as the best film Alfred Hitchcock never made. I was onto something as it was based on a novel by Patricia Highsmith who wrote the Hitchcock classic Strangers on a Train (1951) which I had not yet seen at the time. The Talented Mr. Ripley made me think of another Hitchcock classic To Catch a Thief (1955). It was a marvelous mystery with sumptuous sounds and cinematography making the viewer wish they could transport themselves to 1950’s Italy and take in all the food and sounds of jazz back when that was the new music on the radio kids were torturing their parents with. The performances across the board were spectacular with Matt Damon as the lead role, his biggest since his Oscar winning breakout hit Good Will Hunting (1997), and this was Gwyneth Paltrow’s biggest role since she won an Oscar the previous year for Shakespeare in Love. This was also director Anthony Minghella’s first film since his Oscar winning epic The English Patient (1996). Jude Law would be the only performance to get recognition from the Academy with a Best Supporting Actor nod but Philip Seymour Hoffman may have given one of his best supporting turns as his friend who seems to be lurking around the corner and knows something Matt Damon’s Tom Ripley does not know. This was a box office success in late December of 1999 and when the Academy Award nominations were announced many including myself were shocked this film was omitted from the Best Picture race and instead replaced by the Miramax feel-good movie The Cider House Rules. The Talented Mr. Ripley is indubitably a better film than that and most of the ones that were nominated for Best Picture that year but the Academy itself was in a very different place twenty years ago. This is indeed still one of the very best films from a great year in cinema. 

5. Man on the Moon (directed by Milos Forman)

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Much has been said and maligned about Man on the Moon since it was released and lost a box office battle with Deuce Bigalow: Male Gigolo. With the new Netflix documentary Jim and Andy audiences see how intolerable Jim Carrey was to work with wreaking havoc on the set with his method acting. This was the biggest under performer of Jim Carrey’s career up to this point since his breakout year of 1994 with three hit films Ace Ventura: Pet Detective, The Mask, and Dumb and Dumber. Carrey was no longer the king of comedy, that torch was now passed to Adam Sandler who had the huge summer hit Big Daddy and then produced his friend Rob Schneider in Deuce Bigalow. Man on the Moon was still an inspiring biopic directed by Milos Forman, the king of that sub-genre with films under his belt such as Amadeus (1984) and his prior directorial effort The People vs. Larry Flynt (1996). When Man on the Moon failed at the box office it meant there would be no absolution for Jim Carrey from the Academy Awards who failed to nominated him for Best Actor in The Truman Show the previous year. He has since starred in many great films but has never been nominated for an Oscar. Many point to the moment he was on the Awards show and talked out of his butt as the moment the Academy decided to shun him, but his performance as Andy Kaufman was worthy of their recognition for at least a nomination. Man on the Moon is still a powerful and movies picture that can stand on its own merits as one of the best films of 1999. 

4. Three Kings (directed by David O. Russell)

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No film hit the awards scene like a searing bullet to the gallbladder as much as David O.Russell’s war-comedy-epic Three Kings. The Persian Gulf War had come and gone without much fanfare, the only previous film to tackle that recent conflict was the outstanding Edward Zwick film Courage Under Fire (1996) with Denzel Washington and Meg Ryan that was criminally ignored by Oscar voters. The same fate would come to Three Kings. With no idea that bigger wars in the middle east were only two years away on the horizon, Three Kings felt like a war fable for American greed and victory. It took the plot from Kelly’s Heroes (1970) but made it relevant for 1999 a time when American males were lost without a war, without a cause, without a reason to fight. These guys faced nothing but heat and confusion, and the chance to get rich quick by stealing gold that belonged to Saddam Hussein. Of course on the journey they find themselves as well as a reason to fight and save Iraqi people from oppression. Three Kings was shot and edited in an unconventional manner with colors and timing altering what the viewers saw to evoke a sense of surreal elements into the brutal reality of the war. Today Three Kings is mostly a forgotten gem. A footnote in the careers of actors George Clooney and Mark Wahlberg, and a stepping stone for filmmakers David O. Russell and Spike Jonze but for whatever my opinion is worth, this is still the best film of Mr. Russell’s career. He struggled for the next decade to finance his visions and it was not until The Fighter (2010) when he found his niche and the Academy Awards started eating up his movies like a cat with catnip. 

3. Magnolia (directed by Paul Thomas Anderson)


The most bold and second most original movie of 1999 belonged to maverick filmmaker Paul Thomas Anderson making a three hour plus epic about intercutting lives in Los Angeles all based on show business. Magnolia is a brave, uncompromising ensemble piece on par with Robert Altman’s masterpiece Short Cuts (1993). P.T. Anderson’s third feature film after his breakout hit Boogie Nights (1997), Magnolia announced that he was an auteur to be reckoned with, sadly he found trouble financing many of his future films in the next decade because they are not viewed as movies that would be commercially successful, Magnolia did not do that well in the box office during the winter of 1999 into 2000 and was met with predictably polarizing opinions from critics and audiences, but had enough to earn Academy Award nominations for Julianne Moore and Tom Cruise in a rare supporting role. Cruise spent over two years filming Eyes Wide Shut and under two weeks filming his parts for Magnolia yet got a nomination for the latter and I would say of the nominees, Cruise deserved it the most. Magnolia is an elegant at times and blunt at times mosaic of life in the late 90’s about coincidence, interpersonal relationships, forgiveness, love, and death. It all builds up to a bizarre storm at the climax the likes of which have rarely been seen outside of the Bible. One of the most invigorating and electric films from its era. 

2. American Beauty (directed by Sam Mendes)


Go on, rip me apart for this. It is so easy to criticize American Beauty ever since it won Best Picture, Director, Actor, and Screenplay at the Oscars dominating the competition but honestly from the other nominees we should be glad this won. It was only a Best Actress Oscar win away from being only the fourth film in history to sweep the big five Oscar categories (Picture, Director, Actor, Actress, and Screenplay). It was only the second film to win Best Picture during the 90’s that was not a historical epic of some sort (1991’s Silence of the Lambs was the first and only other non-history based Best Picture winner). American Beauty took independent themes and styles and made them mainstream for most audiences making it feel special to the general public. But there was more to this film. American Beauty captures what bored suburbia looked like in the 1990’s better than practically every other movie. Plus, few movies captured how adults and teenagers both felt trapped in a mundane existence as well as this film. Some of the cinematography may seem obvious with the bars in the computer screen meant to evoke a prison, or the rose petals, and the floating bag. It is easy to use disgraced actor Kevin Spacey as a punching bag and he does play a pedophile in this film, but honestly this is a monumental performance that not only deserved the Best Actor trophy but also it is hard to imagine any other actor playing Lester Burnham other than Spacey without the movie being completely different. American Beauty is as entertaining as it is challenging, as a slice of life and darkly comic social commentary on marriage ,school and the disintegrating family values for superficial items. I loved it in 1999 and I will still defend this movies strength’s in 2019. 

1. Being John Malkovich (directed by Spike Jonze)


The most original movie of the year was also the best movie of the year. A brilliant comic fantasy that kept me guessing and on the edge of my seat in ways that no movie ever had before. Featuring career best performances from Cameron Diaz (shunning her usual gorgeous looks to play frumpy) and John Malkovich as himself being inhabited by other characters as the film progresses. Catherine Keener earned a well deserved Oscar nod but this movie should have gotten more than just three nominations for Best Director, Supporting Actress, and Original Screenplay. It should have won all of those and then some. During its release in the fall of 1999 and awards season the following winter, critics loved Being John Malkovich but nobody quite knew what to really make of it. Since then there have been more cerebral and psychological human comedies and Charlie Kaufman has turned his screenwriting into sort of his brand. Spike Jonze has struggled to get his visionary films made but did win a well deserved Screenplay Oscar for Her (2013). Being John Malkovich is a wild and enlightening head trip that is so much fun to go into that portal again and again. One of the most inventive and unique movies of the past 20 years. 

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