25 Years Later – The Best of 1999 in Film: Part 1

December 20, 2024

As long as I can remember, I’ve been a numbers guy.  It worked out for me that I got a college degree in Accounting and spent my career in jobs where I could quickly analyze numbers and make decisions.  Even today in my volunteer work, I mentor clients (mostly) on financial matters.  I often tell them that my brain thinks in rows and columns, like an Excel spreadsheet.  One of the benefits of doing this blog is that I get to exercise the other side of my brain – the creative one.  Of course it also gives me an excuse to watch more movies than the average person.

Being a numbers person also means that I associate events in the world (or my personal life) to certain years.  2004?  Easy – it was the year the Red Sox finally won the World Series.  1984?  A phenomenal year in music – Springsteen’s Born in the U.S.A, Prince’s Purple Rain, Madonna’s Like a Virgin, and so on.  2001 is one that we all remember for horrific reasons.  2020?  Yeah, as much as we’d like to forget that crazy year, I don’t see that happening anytime soon.  And then there’s 1999.

What’s the first thing you think of when you hear 1999?  End of the century?  Well, technically that was the year 2000, since there wasn’t a year zero.  Remember that silly debate?  It was even the plot of a Seinfeld episode.  The end of the 20th century (however you define it) was the early days of the internet.  Dial-up internet and America Online connected us to the nascent world of interacting with people through new means.  I remember exploring an AOL page on my work laptop (with a black and white screen, naturally) and feeling dumbfounded that I could read an article about a football game that had literally just ended on my TV. 

Of course, this was also the year of the Y2K panic, which (thankfully) turned into much ado about nothing.  Speaking of which, there is a new comedy-horror movie that explores what would have happened if the machines really did rise up and turn against us at 12:00 AM on January 1, 2000.  Y2K is centered around a group of high-school students who gather for a New Year’s Eve party, only to find that they are in for hell unleashed by the machines who have gone haywire.  It’s an interesting and funny premise and the first half of the movie mostly works.  Unfortunately the film falls off in quality in the second half as it is neither funny enough or scary enough to be successful.  No reason to put that one on your list.

1999 was also a phenomenal year for movies, which means it’s a perfect excuse to take a look back at my favorite films from that year.  Twenty-five years ago Hollywood was still turning out blockbuster pictures across a number of different genres.  After 16 years, George Lucas brought Star Wars back into our lives with The Phantom Menace, the first of his three prequel films.  Moviegoers were captivated by the found footage horror sensation The Blair Witch Project.  And most importantly, the top ten films at the box-office had variety.  We had children’s movies (Toy Story 2 and Tarzan), romantic comedies featuring Julia Roberts (Notting Hill and Runaway Bride), silly comedies featuring Mike Myers and Adam Sandler (in a time when people weren’t easily offended by comedies), an innovative science-fiction story about a desolate future, and the surprise ghost story that defied the odds as one of the top earning films of the year while also receiving several Oscar nominations.  In other words, “We used to be a proper country.”  I’m only partially kidding – 2024 was another fantastic movie year, as I will cover in more detail next month.  But almost all of the top ten films of 2024 have been sequels.  Clearly the studios need to do a better job of getting the great original stories they are producing in front of wider audiences.  As I always say, “Let people see your movies!”  But that’s an argument for another day. 

Let’s Talk About the Oscars

We’re going to begin our examination of 1999 in movies with a look at the Academy’s nominees for Best Picture, starting with two films I would have swapped out with better options if I was in charge.  The Cider House Rules and The Green Mile were not surprising nominees at the Oscars, since they are both adaptations of novels by beloved authors.  That archetype is right up the alley of the typical Academy voter in the late 1990s. 

The Cider House Rules is the portrait of a boys orphanage, adapted from the John Irving novel of the same name.  Michael Caine (who won an Oscar for his performance) plays the doctor who oversees the dozens of children desperate to find a permanent home, while also caring for mothers who come to his care when they have an unplanned pregnancy.  He mentors young Homer, played by Tobey Maguire, to take over for him someday, but Homer has other goals – he wants to leave the only home he has ever known to explore the world.  The Cider House Rules is a perfectly fine movie, but not one that resonates for anything groundbreaking 25 years later.  It’s sweet and sentimental, helped by likable actors giving solid performances.  That being said, the cynic in me much prefers the Irving adaptation The World According to Garp, the biting satire with Robin Williams and Glenn Close released in 1982.

You don’t normally expect a Stephen King adaptation to resonate with Academy voters, but 1994’s The Shawshank Redemption was nominated for seven Oscars.  Of course, it wasn’t a typical King horror movie, which would have likely alienated Academy voters.  The director of that film (Frank Darabont) returned five years later with another King adaptation, The Green Mile.  The story of a prison guard (played by Tom Hanks) who must deal with a new inmate on death row, who may or may not have supernatural abilities, was adapted from King’s 1996 serial novel.  I actually remember reading this novel when it came out, because its release strategy was unique for the time.  King chose to release the novel in six parts, with each “mini-novel” arriving once a month for six months.  It was a pretty cool gimmick, as I remember quickly devouring each installment and anxiously awaiting the next release. 

The film adaptation of The Green Mile is faithful to the book, probably to a fault, as the movie clocks in at over three hours.  We learn about the inmate (played by Oscar nominee Michael Clarke Duncan) and his crimes, as well as his special powers that play out a few times throughout the movie.  The rest of the cast is strong, but the film is saved by Hanks, who is excellent as the reserved but determined leader of the prison guards.  The Green Mile has a good payoff, even if King’s supernatural plotlines don’t always translate well to the big-screen (see IT: Chapter Two), but it takes a long time to get there.  Unless you’re a completist for Best Picture nominees or Stephen King adaptations, The Green Mile is one you can probably skip.

Now, if I had my choice, I would have swapped in Paul Thomas Anderson’s Magnolia and the brilliant thriller The Talented Mr. Ripley (both of which I will cover next week) in place of these two nominees.  These two films are ones that I know will continue to rewatch, whereas I will likely never revisit The Cider House Rules and The Green Mile.  To me, Best Picture nominees should be movies that not only capture the essence of the particular year in film, but also resonate for several years afterwards, which brings me to my next selection.

An Underrated Masterpiece – The Insider

You can’t go wrong with a journalism thriller.  Heck, I dedicated an entire blog post to the genre (which you can read here in case you missed it) where I first wrote about my love of The Insider, director Michael Mann’s look at a 60 Minutes investigation into Big Tobacco.  Russell Crowe is outstanding as Jeffrey Wigand, a whistleblower with a large tobacco company who is convinced (pressured?) by 60 Minutes producer Lowell Bergman (Al Pacino in a lights-out performance) to go on the record about his company’s negligent actions.  This was in the midst of Crowe’s incredible run, when he starred in five Best Picture nominees in seven years, and won a Best Actor Oscar for Gladiator.  He also could have won for The Insider and A Beautiful Mind.

There are many qualities to love about The Insider.  We have the tortured Wigand, debating putting the safety of his family and himself at risk by violating his non-disclosure agreement in the interest of serving the public interest.  Bergman is balancing managing his reluctant witness while the corporate executives at CBS are pressuring him to drop the story for fear of crippling lawsuits from the tobacco companies.  Director Michael Mann combines the drama of these two storylines together in a perfect way, with elements of people in rooms debating the ethics of journalism, complementing the thrilling scenes where Wigand’s anxiety begins to get the best of him.  It helps that The Insider has a deep cast, including Christopher Plummer as Mike Wallace, and many other recognizable faces. 

Mann’s filmography is an interesting one.  While he has had his share of misfires, his best movies (The Insider, Collateral, The Last of the Mohicans, and Heat) are some of the more iconic films of this era.  The Insider is my favorite of his movies and was well-deserving of the Academy’s seven Oscar nominations, even if it didn’t earn any wins.

A New Voice in Filmmaking Arrives – The Sixth Sense

The Academy is not known for recognizing scary movies, aside from some truly iconic films, like The Exorcist (nominated in 1973) and 1991’s Best Picture winner The Silence of the Lambs.  So, it was a bit of a surprise when The Sixth Sense received six nominations, including Best Picture.  And while some may consider this a horror movie (after all, there are ghosts and some scenes are downright scary), it’s more of a thriller – it even says so on the poster above!

Of all of the nominees this year, this is the one that meets the intersection of “capturing the zeitgeist of the movie year” with meaningful resonance several years later.  Even knowing the iconic twist ending from director M. Night Shyamalan, The Sixth Sense is eminently rewatchable.  It helps that he recruited Bruce Willis to headline this film, which helped people take it seriously when it was released.  Haley Joel Osment and Toni Collette (both nominated for their performances) are both excellent, and Shyamalan demonstrated his filmmaking talents with his clever camera work and use of color and sound.  You can tell that he is a fan of the greats of cinema like Hitchcock and Spielberg. 

Following the release of The Sixth Sense in theaters, word-of-mouth spread and the film became the second biggest grossing movie of the year, behind only The Phantom Menace.  Of course, a surprise twist ending like the one featured in The Sixth Sense could never stay secret today.  Hell, we have heathens recording parts of movies from their theater seats today.  Not only do I regularly see this on social media, but I actually witnessed someone doing this at a screening of The Outrun a few months ago.  I was stunned and did a triple take to confirm what I thought I was seeing.  When did people forget that going to the movie theater is not the same as sitting on your couch in your living room?  Put down your phone, keep the talking to a soft whisper and let the magic of moviemaking wash over you!  Ok, rant over.

Anyway, The Sixth Sense launched the career of Shyamalan, who is still delivering quality (if imperfect) films 25 years later.  One drawback to the success of his breakout hit was the expectation that every one of his movies would feature a twist ending, and if it wasn’t better than The Sixth Sense (how could it be?), it was deemed a disappointment.  I’m still a fan of his work, even if he will unlikely capture the magic of The Sixth Sense.  At least he keeps trying to entertain audiences with original stories.

The Winner – American Beauty

After almost 100 years, it’s natural to expect that there will be choices for Best Picture that don’t age well.  Times change, sensitivities change, some storylines and characterizations of roles are downright offensive when looking back years later, and certain filmmakers and actors are discovered to be deplorable human beings.  I have a pretty easy time separating the art from the artist when I’m watching a film.  I won’t pretend to be easily offended by an individual’s actions when evaluating their work – they are in the creative field, after all. 

Needless to say, we can’t discuss the 1999 winner for Best Picture without mentioning the disgraceful fall of Kevin Spacey, who won Best Actor for his performance in American Beauty.  It also doesn’t help that part of the plot includes his character leering after the teenaged friend of his daughter.  That being said, I loved American Beauty when I saw it in 1999 and after rewatching it recently, I still think this is a quality film, even if it wasn’t the best movie of 1999.

American Beauty is a portrait of a family in crisis, when a middle-aged couple realizes that, despite achieving everything you are “supposed to get” (job, house, car, family, friends), happiness just doesn’t happen.  Suburbia, as it turns out, is not the happy universe it’s sometimes made out to be.  Spacey is terrific as Lester Burnham, the textbook definition of a loser suburban husband and father who has no respect from his family and co-workers.  Lester is married to Carolyn (Annette Benning), who cares more about her rose garden and keeping up appearances than her family.  Lester and Carolyn’s daughter Jane is also miserable, hanging out with her phony best friend Angela, while also catching the eye of her mysterious neighbor Ricky.  Lester is rejuvenated when quits his job, starts working out (to impress his daughter’s friend – ick), and smoking pot with Ricky.  He decides life is too short to be miserable, as does Carolyn who begins an affair with rival real estate agent Buddy, the King of Real Estate.  Alas, things do not get better – they only get worse.

At the time of its release, the film was praised for its depiction of suburban life, with beautiful cinematography, a haunting score, and a clever screenplay.  Its combination of melodrama and black comedy hit a perfect note with audiences and Academy voters alike.  In addition to Best Picture and Best Actor, Sam Mendes (Best Director) and Alan Ball (Original Screenplay) were honored for their first feature film, a rare achievement.  I take exception with Benning being passed over for Best Actress in favor of Hillary Swank (for Boys Don’t Cry), admittedly a movie I haven’t seen.  Swank would beat her again five years later and it still baffles me that Swank (a perfectly fine actress) has two Oscars and actresses like Benning, Amy Adams and Glenn Close have none.  Oh well, that’s the Oscars for you.

Over the last twenty-five years, American Beauty has moved up the list of Best Picture winner travesties, for a few reasons.  Not only do you have the cringe-worthy plot with Lester and Angela as well as Spacey’s exodus from Hollywood for sexual harassment and assault allegations for his despicable behavior.  There has also been backlash against the portrayal of the rich White suburban family who can’t be happy, despite “having it all”, as well as the depiction of Ricky’s father as a crude stereotype character that feels forced and not genuine.  Alas, no film is perfect and I can look past the flaws of American Beauty and appreciate it for what it is – a funny, but melancholic portrait of an American family that is beautiful to look at with a memorable score, even with a few cringe worthy scenes.

Iconic Comedies

From the serious to the decidedly unserious.  Sometimes you just need a silly comedy to forget about the trouble in the world and make you laugh.  Sure, the plot may be stupid, but if there are likable characters and funny moments, you will keep coming back to these movies.  First up is the creation of a comedic genius who we first discovered on our television every Saturday Night.

Mike Myers had such a fun time, not to mention incredible box-office success, with 1997’s Austin Powers: International Man of Mystery, that he decided to run it back two years later with Austin Powers; The Spy Who Shagged Me.  Myers created the British agent (a spoof on James Bond and the Pink Panther films) who is transported from the swinging 1960s London scene to the 1990s to help capture his arch nemesis, Dr. Evil (also played by Myers.)  Unfortunately, Powers is easily distracted by trying to (ahem) shag every woman he encounters, starting with his fellow agent Felicity Shagwell (naturally), played by Heather Graham.  Dr. Evil has also expanded his cast of villains to include the disgusting (but appropriately named) Fat Bastard, also played by Myers under several pounds of latex and makeup. 

Listen, the Austin Powers movies are ridiculously juvenile, aimed at teenage boys, which probably explains why I find them funny.  Sure, some of the jokes are beaten to death and don’t always land, but anytime Dr. Evil is on screen, I can’t help but laugh.  His interactions with the clone who is 1/8th his size (Mini-Me) and his rebellious son Scott are top-notch.  While I prefer the first film in the series, the second installment is still a worthy follow up.  If you want to shut your mind off and laugh at the brilliance of 1990s Mike Myers, this is a good place to start, as is our next selection.

You know you are in good hands when the opening scene of a movie resonates with you immediately.  As Office Space begins, we are with Peter (played by Ron Livingston) on his way to work, stuck in traffic.  He has “lane envy”, constantly switching lanes to what looks like the quickest one, only to realize the lane he just left is now moving faster.  His life is summed up when he looks over to see an elderly man using a walker moving faster down the sidewalk than he is moving down the street.  Thus begins another hellish day at Initech, the bland corporation where he works.  Peter has to spend eight hours every day in his cubicle, lamenting his meaningless life with his friends, while trying to tolerate his annoying co-workers and loathsome boss.  His fortunes turn around  when he gets stuck in a hypnosis limbo, leaving him unable to care about anything in the world except having a good time.

It’s not surprising that an absurdist comedy written and directed by the man who gave us Beavis and Butthead (the very talented Mike Judge) would not only be funny, but spot-on in depicting life in a Corporate office.  I mean, who among us hasn’t wanted to destroy a printer with a baseball bat?  Or had to take a deep breath when a co-worker said something that almost pushed you off the deep end?  Or had to deal with efficiency experts like the Bobs?  Or had a boss who clearly had no clue?  Office Space is one of those movies that has lived on through online memes and hysterical quotes, always a sign to revisit it after 25 years.

The Future Looks Bleak – The Matrix

Earlier this year I had a chance to see the 25th anniversary re-release of The Matrix in the theater.  I’ve seen the film a few times over the years and remember the plot pretty well, but it was still incredible to see a visionary movie like this on the big screen.  Now, thankfully our world today doesn’t look like the future that the Wachowski siblings (who wrote and directed the film) predicted when we first saw the movie.  Sure, things are bleak at times, but not that bad right?  Well, I guess it depends on your perspective and the shitshow news headline of the day. 

Keanu Reeves had been stumbling through the ups and downs of being an actor in Hollywood when he was cast as Neo, the protagonist of The Matrix.  He is recruited by Trinity (Carrie-Anne Moss) and Morpheus (Laurence Fishburne) to help their cause, believing he is the chosen one.  They open up his mind to reveal that long ago machines took over the world and he has been living in a simulation.  (Insert Keanu “Whoa” meme here.)  From there, the movie evolves into an incredible action film that features groundbreaking special effects that we had rarely seen on screen before.  Watching characters fly through the air while battling, dodging bullets coming at them, and moving hyper-fast while fighting their enemies left us all uttering “Whoa,” just like Keanu.

The Matrix showcased innovating filmmaking techniques and delivered a smart science-fiction picture that effectively combined action with a compelling plot.  Like most successful movies of the 1990s, we saw several sequels that unfortunately devolved in quality with each installment.  The third movie is baffling to me, but I thought the fourth film released in 2021 was decent.  Thankfully Reeves was able to start another franchise ten years ago with the release of John Wick.  Now that series, despite an overindulgence of violence, feature excellent movies that I know I will keep coming back to.  It’s great to see Reeves, who seems like a pretty down to Earth guy, have so much success after almost forty years in the business, and The Matrix is one of his better known roles, and an iconic movie that represents the best of 1999 in film.

That’s all for this week’s post.  I’ll be back next week with part two of my look at the best films of 1999, including more crazy comedies, Matt Damon’s most impressive performance, two messed up movies about losing your mind, and two iconic Tom Cruise films, one of which is my favorite Christmas movie that is not really a Christmas movie.  Thanks for reading and if you’d like to be notified of future posts, you can subscribe below.

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