As has been the case with all my previous retrospective lists (1997, 2007, 2008), looking back at the world in film twenty years ago has been a very rewarding experience. Perspective is something that is painfully missing every awards season as most awards contenders are declared great barely months after they have first been seen. In a similar vein it is usually the most conventionally successful movies that soak up most of the attention of the general public. Even in the realm of art and indie films, it is the most easily digestible and understood movies that initially garner notice.

But time affords perspective. Time allows flaws to be found in movies once called unquestionably great. It also allows for hidden gems, misunderstood masterpieces, and movies ahead of their time to emerge. And most importantly, the passage of time allows me time to (presumably) get wiser. My teenage self in 1998 would have found space on this list for The Wedding Singer, There’s Something About Mary, Enemy of the State, and Michael Bay’s Armageddon. Thank goodness I have a chance to correct that.

(Note: For this list, a movie is eligible if it had its initial wide-release anywhere in the world. This will matter most with foreign films as often-times they would show up for a North American release years after their initial release in a local market. This is why a movie like Wong Kar Wai’s Fallen Angels, which was released in America in 1998 but actually released in 1995 in Hong Kong, is not on this list.)

But before we dive into what I consider the best films of 1998 (your list may differ) let’s remind ourselves what the film landscape actually was in 1998:

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TOP BOX OFFICE MOVIES (North America Gross in USD):

1. Saving Private Ryan ($216,540,909)
2. Armageddon ($201,578,182)
3. There’s Something About Mary ($176,484,651)
4. A Bug’s Life ($162,798,565)
5. The Waterboy ($161,491,646)
6. Doctor Dolittle ($144,156,605)
7. Rush Hour ($141,186,864)
8. Deep Impact ($140,464,664)
9. Godzilla ($136,314,294)
10. Patch Adams ($135,444,603)

(Figures from Box Office Mojo)

This box office list is bizarre on several levels when compared to our own current box-office landscape. Most notably there are exactly zero sequels on this list with only Godzilla being a remake of another property. Rush Hour is the only movie only movie on this list that would even have sequels. But beyond the lack of recognizable and repeatable intellectual properties on this list several other things stand out.

First, amazingly at least half of these movies can be categorized as comedies, with the top-grossing one even being an unabashedly raunchy R-rated comedy (There’s Something About Mary). A quick glance at the 2018 North America Box Office as of writing finds the top grossing comedy currently sitting at number 11 (Crazy Rich Asians) while the highest R-rated comedy comes in at number 25 (Game Night). This is perhaps unsurprising given the shift of importance the international box-office has had in the intervening decades but it is still somewhat of a shock to see the cratering of comedy as a box-office draw.

Meanwhile, I count only three movies that bear any real resemblance to modern-day tentpole blockbusters (Armageddon, Deep Impact, Godzilla) where that is exclusively what the top-8 movies of 2018 are. Instead bookending the top 10 box office movies of 1998 are the kind of movie that has gone nearly extinct: serious dramas whose primary target is an adult audience. In fact the top-grossing movie of 1998 is an even rarer beast today: a serious R-rated drama that is primarily an awards-season play (Saving Private Ryan).

Of course before we make some haranguing cry about how today’s Hollywood is creatively bankrupt and what not, let me point out one clear difference between 1998 and 2018. The average Metacritic score for the Top 10 in 1998 is an abysmal 55.2 while in 2018 the current Top 10 gets an average score of 70.7! That first of all puts a wet blanket on the lazy argument that critics today are out-of-touch elites who don’t know what the public like. But more importantly it also stands as a clear rebuttal to the claim that Hollywood’s large abandonment of original movies is a sign of its creative bankruptcy. In 1998, Hollywood was churning out tons of originals that the public was eating up. And they were for the most part terrible. Clearly in 2018 there is a clear correlation between critical acclaim and box office receipts, a sign that the demand for creative excellence in our entertainment is something studios are clearly paying heed to. And that should give us some hope that we are not completely doomed as a species.

ACADEMY AWARDS

WINNER: Shakespeare in Love
NOMINEES: Elizabeth, Life is Beautiful, Saving Private Ryan, The Thin Red Line

I’ve said this several times before so I won’t belabor the point: This is without a doubt one of the biggest Oscar mistakes of all time. The fact that Shakespeare in Love won in no small part thanks to the strong-arm campaigning tactics of its producer, and now deservedly disgraced Hollywood pariah, Harvey Weinstein simply adds to the overall illegitimacy of it beating Saving Private Ryan which was, if not the best picture of the year, at least the best with an actual shot at winning.

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20. YOU’VE GOT MAIL dir. Nora Ephron

I will grant you that the final scene in this movie is among the schmaltziest drivel ever written. And I will also grant that the movie breaks exactly zero new ground in either the genre of romantic comedy or filmmaking in general. But take away those two obvious complaints and what you have left is a sophisticatedly written comedy by Nora Ephron who manages not just to capture the then-emerging world of online dating and curating our digital lives but does so in such a way that still feels shockingly timely today. In Tom Hanks and Meg Ryan you have what could easily be the most charmingly lovable couple ever assembled who thankfully avoid the trope of requiring an Idiot plot to keep them apart. The romantic comedy gets frequently shortchanged when it comes to “Best-of” lists – it would seem a crime to deny a spot here to one of the best of the genre.

(Note: Author acknowledges that since Kathleen Kelly as portrayed by Meg Ryan represents the first woman he ever fell in love with, his opinions about this movie should be taken with a huge helping of salt.) 

19. LOCK, STOCK, AND TWO SMOKING BARRELS dir. Guy Ritchie

Lock, Stock, and Two Smoking Barrels is less of a crime movie as it is a madcap screwball comedy dressed up as one. The movie starts with a group of four friends finding themselves having to repay an enormous gambling debt to a porn kingpin, and quickly snowballs from there. By the time the movie concludes they find themselves knee-deep in calamitous trouble as five different parties of competing interests and goal clash repeatedly with one another, gumming up each other’s plans, and trying to come up on top. Like any great screwball comedy there are so many moving pieces as to make your head spin but director Guy Ritchie proves himself more than capable in navigating this controlled chaos in what is probably his best film.

18. THE LAST DAYS OF DISCO dir. Whit Stilman

The brilliance of Whit Stilman’s The Last Days of Disco is that it follows a group of rich, white, young, conventionally attractive, highly educated, and generally successful people who find themselves discontented with their bourgeoise lives and choose as the symbol of their rebellion, youth, and liberation, of all things, disco – easily the most inoffensive of the music forms, especially in the early 80s when this movie is set. And somehow Stilman, through his fantastic penchant for dialogue and comedy makes you not want to completely loath these entitled people and even makes you sort of want to root for some of them. A truly remarkable achievement indeed.

17. SHAKESPEARE IN LOVE dir. John Madden

The great shame of this movie stealing the Oscar win from Saving Private Ryan is that it saddled the movie with a reputation of being nothing more than Oscar bait. While it most definitely did not deserve to win the Oscar, Shakespeare In Love is still a really good movie. Featuring a stellar cast at the top of their game, a witty script that manages not to descend into cheese while believably sounding like a Shakespeare play, and a production design team working full tilt to create and immersively believable Victorian world, it is a fun and breezy romantic comedy that is working at a high-level of difficulty and managed to pull it off.

16. SLUMS OF BEVERLY HILLS dir. Tamara Jenkins 

It is absolutely criminal that this movie is not more widely known. It features a phenomenal cast of comic actors in Alan Arkin, Marisa Tomei, Carl Reiner, David Krumholtz, Jessica Walters, and a revelatory debut performance from Natasha Lyonne (of Orange is the New Black fame). Tamara Jenkins weaves a brutally honest and painfully funny coming-of-age story in the 90s when such frank talk about puberty, sexuality, and womanhood was still hardly in vogue. Now in a world where Broad City, Girls, Inside Amy Schumer and even network shows like Jane the Virgin and Crazy Ex-Girlfriend among a host of others have shattered prudish views of womanhood and sexuality from mainstream media, it is time for Slums to be rediscovered again.

15. PI dir. Darren Aronofsky

Darren Aronofsky’s debut film has the look and feel of a student film that is desperately trying to evoke David Lynch’s Eraserhead, but it is undoubtedly the best version of that sort of movie. This claustrophobic movie gets inside the head of Max Cohen, a reclusive mathematician who inadvertently stumbles upon a sort of “God-code” when running a program to try and predict the stock market. This code seemingly allows him to understand and predict just about everything within the natural universe which sets him up as one to be pursued. But impressively, it is Aronofsky’s direction which never lets us truly know Max is a genius or insane that heightens the thrilling nature of this movie, and makes it more than worthy as a spiritual successor to Eraserhead.

14. FESTEN dir. Thomas Vinterberg

The underlying philosophy of the Dogme 95 film movement is sanctimonious and slightly odious with its holier-than-thou approach to cinema. There is also the undoubted evidence that the movement produced some fantastic movies and nowhere is that more clear than in the first Dogme 95 movie Festen (released as The Celebration in North America). The movie focuses on a family during the patriarch’s 60th birthday party when his adult son reveals his father’s long-secret incest, leading to a volatile and darkly humorous story in which we witness the disintegration of civility, decorum, and familial bonds. In other words, a truly awful but always compelling time.

13. VELVET GOLDMINE dir. Todd Haynes

With David Bowie’s unexpected passing in 2016, it is much easier view Velvet Goldmine less as an accurate depiction of the glam-rock era, but rather as a splendiferous celebration of its music, ideals, and of course, the iconic people who founded the movement. With Jonathan Rhys-Meyers channelling David Bowie as the pouty Brian Slade, and Ewan McGregor successfully filling in as Iggy Pop stand-in Curt Wild, the duo frequently allows us to bask in stage performances that propel us straight into the glories of glam-rock. It is a kaleidoscope experience several years ahead of the curve, and a fitting, if thinly veiled, ode to Bowie and the sexual awakening he inspired.

12. RINGU dir. Hideo Nakata

The grand-daddy of modern Japanese horror is notable not just for being a terrifying watch but for bringing about a global revitalization of the horror genre whose aftereffects can still be felt two decades later. The movie combines our obsession with the supernatural and our anxieties about the advent of technology so perfectly as to make even the act of watching television, the most mundane of human activities, turn into a sinister source of dread and terror. While the American version is the rare remake that actually manages to capture what makes the original so special, there is no substitute for the haunting Ringu.

11. DARK CITY dir. Alex Proyas

Before The Matrix would so thoroughly thrust philosophical and existential science-fiction into the mainstream, Dark City covered the same ground and in more terrifying fashion. Set in a world where a strange group of creatures called the Strangers resets the memories of all the people living in it every time the clock strikes 12 and inserts new storylines for its citizens to carry out, it calls into question the nature of personhood: who are we without our memories? Rufus Sewell plays Murdoch, a human who suddenly finds himself immune to the memory swipe at a most inopportune time, and is forced to dive deep into the belly of this society to find its horrifying truth.

10. OUT OF SIGHT dir. Steven Soderbergh

Out of Sight finds the previously exclusively indie-film director Steven Soderbergh take a stab at a more conventional movie and find that it suits him very well. Featuring a star at the start of his eventually illustrious careers (George Clooney), an actress at the top of her game (Jennifer Lopez), and a cavalcade of great supporting actors in Ving Rhames, Don Cheadle, Albert Brooks, and Dennis Farina, it is a crime movie less interested in providing us the thrills associated with the genre, even though the thrills are present. Instead it finds the most joy in pitting the characters against each other in witty, funny, and often where Lopez and Clooney are concerned, very sexy ways. It also just might be the best adaptation of an Elmore Leonard novel, which is saying something.

9. FLOWERS OF SHANGHAI dir. Hou Hsiao-hsien

Hardly anything happens in Flowers of Shanghai. We move from room to room in four brothels sitting intrusively in private conversations of the brothels’ courtesans and the men who pursue them. We never see the outside world, and yet through their conversations we learn of the courtesans’ hopes and dreams, their pains, the petty things that keep them amused, and the subtle politics and social expectations that keep them locked in their places. And through these innocuous meetings, we get a full picture of the world in which they live in. The opiate haze that seems to permeate this movie affects us as we are forced to slow down and listen, with as much being revealed by what is not said as the words they actually speak.

8. RUN, LOLA, RUN dir. Tom Twyker

Like a parent who sneaks vegetables into their kid’s food by smothering it in cheese, Run Lola Run is the ultimate bait-and-switch movie. It is dressed up in techno music, has a punk-rock sensibility, and is a frenetic action movie from start-to-finish. Yet it is also a German film that is as concerned with fate and chance, the butterfly effect, and existential angst as it is with providing pure entertainment. In other words, it is the perfect vehicle to sneak some foreign art film exposure on your unsuspecting friends.

 

7. A SIMPLE PLAN dir. Sam Raimi

Nothing corrupts good people faster than money. This is the maxim by which Sam Raimi operates when crafting this small-town crime movie. When Hank (Bill Paxton), a man well-versed in the ideology and theology of the American dream, stumbles upon $4 million in cash deep in the Minnesotan woods along with his sad sack brother Jacob (Billy Bob Thornton) and Jacob’s best friend Lou (Brent Briscoe), their well-calibrated lives are suddenly thrown out of alignment. Hank’s simple moral code erodes as the possibility of getting away with keeping the obviously illegal stash of money becomes a possibility. But as is typical for instant criminals, talking about how to get away with it and actually getting away with it prove to be two very different propositions.

6. THE THIN RED LINE dir. Terrence Malick 

After twenty-years away from the scene Terrence Malick returned to filmmaking with his breathtaking The Thin Red Line. Where Saving Private Ryan captured the terrifying and visceral scale of war, answering our questions as to what the modern battlefield looks like, Malick’s The Thin Red Line asks the question why? Deliberately oblique, Malick paints a lyrical and poetic picture of modern war; he is less interested in individual stories of heroism to inspire us and instead frames his movie in the context of the psychological battles soldiers fight in order to fight in war as he uses a ridiculous amount of stars (most of them criminally underutilized) to thrash out just about every view of war. That Malick does not seem to have any definitive answers to the questions he raises about the nature of wars and why we fight them may be frustrating from a traditional narrative standpoint, but it may also be honest.

5. THE TRUMAN SHOW dir. Peter Weir

Of all the movies on this list, The Truman Show has the strongest claim for being the most prophetic. It tells the story Truman Burbank (Jim Carrey), a man who has unsuspectingly lived his entire life on a soundstage being broadcast twenty-four hours a day. And by doing so it chillingly anticipates the reality-TV revolution that epitomizes so much of our current entertainment landscape, including our questions about whether reality-TV truly captures life, the ethics of manipulating people for our entertainment purposes and, as Truman himself shows, what it means if someone can live authentically in the heart of artifice. The movie also represents the significant moment in which Jim Carrey showed he was more than just a manically talented comedian, and we have all been the better for it.

4. SAVING PRIVATE RYAN dir. Steven Spielberg

Simply put, I doubt there has been a single movie that has had a more pronounced impact on its genre than Saving Private Ryan and the war movie. Before Saving Private Ryan, we were treated to a glut of extremely reverent but generally sanitized depictions of war and the soldiers who fought them (with a few exceptions). But in Saving Private Ryan Steven Spielberg strips away the Hollywood veneer from war and instead plunges us into the dirt, blood, and chaos of the battlefield, so that we, the safe and secure viewer, finally got to know the terror and horror of war as well as the unspeakable bravery it took to fight in one. Every war film since has had to reckon with the Pandora’s box Spielberg opened as it forever challenged the notion of watching war for entertainment.

3. AFTER LIFE dir. Hirokazu Kore-eda

The central question of the movie is a powerful incentive for self-reflection: if you could only keep one memory with you for all of eternity, what would be? Hirokazu Kore-eda frames this question with this humanistic of a processing centre for the recently deceased where administrative officials interview their subjects to try to help them recreate a memory that will then be meticulously filmed and somehow stored in their memory before they are sent off. Featuring non-professional actors mixed in with professional actors in the various confessionals, it is telling, and damning to most of us, how little conventional standards of success and happiness fails to be mentioned by the subjects. And thanks to Kore-eda meditative style, we can’t help but be faced with that same existential question in the face of our own mortality.

2. THE BIG LEBOWSKI dirs. Joel and Ethan Coen

“The Dude abides”. There was absolutely no way that the most famous slacker in moviedom wasn’t going to be honored on this list in some form. And while Jeff Bridges’ performance as Jeff “the Dude” Lebowski is near-perfection, in which the ability to separate Bridges from his performance is nigh-impossible, it is the supporting cast here that truly vault this movie to its lofty state on the list. Whether it is John Goodman as right-wing nutjob and the Dude’s best friend Walter Sobchak, or Steve Buscemi as their sad-sack bowling buddy Donny, Julianne Moore as Maude the daughter of a much more famous Lebowski who the Dude get mistaken for, or John Turturro in perhaps his finest performance as the great bowling villain Jesus, the cast is so finely tuned to the gonzo plot of the movie that it makes every moment believable even when things are at their absolute craziest. While it is not the Coen Brothers masterpiece, it sure is close.

1. RUSHMORE dir. Wes Anderson

Perhaps it is appropriate that the only person who could possibly beat the greatest slacker in film history (see above) is the greatest student overachiever in film history (in anything except actual academics). Arguably Wes Anderson’s best character, Max Fleischer (Jason Schwartzman) tears through the vaunted halls of Rushmore Academy with the confidence of a jock and the interests of a nerd. He is terrible at actual school-related things like classes and studying, but creates the kind of extracurricular life that the rest of us nerds could only ever dream off. He oozes self-confidence to the point of arrogance (“I saved Latin! What did you ever do!”), ambition to the point of neurosis (as his public school production of a self-penned Vietnam War romance play proves), and oozes the kind of uber-nerd cool the rest of us could only ever dream of having. In other words, well deserving of the top spot on this list, even if he makes you want to punch him in the face half the time.