From Fight Club to 10 Things I Hate About You, from The Matrix to The Spy Who Shagged Me, the year 1999 is highly regarded as one of the best years in film history for good reason. This post will serve as a fond remembrance of that year, A Cute Film Addict style, as we celebrate the best comedy movies or movies with comedic elements from that fantastic last year of the 20th Century.
Welcome to the Class of ‘99, a celebration of the one of the best years in film history. Throughout this post, I will be highlighting some of the year’s best, most entertaining movies, in no particular ranking order. Without further ado, here are some of the best films from 1999.
Austin Powers: The Spy Who Shagged Me
Admittedly, this movie would not be green-lit today. In the context of the current times, Austin Powers is without a doubt a mojo strutting, talking, hip-thrusting #MeToo lawsuit waiting to happen. And yet, the second installment of Mike Myers’s James Bond parody remains enduringly entertaining today. Myers, in perfect form, delivers sensational ear-worm catchphrases and plenty of chaotic energy to drive The Spy Who Shagged Me to the top box office comedy of the year. It could have made trillions, but Dr. Evil settled for billions.
Toy Story 2 The Godfather: Part II of animated films
Toy Story 2 transcends the predecessor and plants the seed that carries the rest of the Pixar franchise forward. What happens to these once beloved little toys when kids grow up? Nowhere does this land better than in the original song from Sarah McLachlan “When She Loved Me” which will make you shed tears you didn’t know you had. It does what Pixar does best, in under four minutes, we learn what happened to cowgirl Jessie (Joan Cusack) when her kid owner grew up; she was forgotten and eventually given away. Pixar has been praised for being able to evoke intense pathos in short, straightforward moments of storytelling. However, Jessie’s origin in song was the first time the studio really tried to deliver this kind of emotional moment, and boy does it hit.
Notting Hill “Just a girl, standing in front of a boy, asking him to love her”
In the ‘90s, Julia Roberts was America’s sweetheart, and a big part of that tag was due to her smile and the chemistry she shared with her co-leads. And both of those are noticeable in Notting Hill, quite possibly the best romantic comedy ever made. In the film, Roberts plays a version of her Hollywood-star self, and the aforementioned smile wins over Hugh Grant’s bookstore owner and his kooky friends the way the sun brightens up a cloudy day. But that smile can’t cover up her character’s sadness or concerns as work and a previous relationship intervene. The real strength of this film lies in the real world struggles that make their way into budding relationships and the presentation here makes this one of the rare intelligent romantic comedies.
Analyze This The Mob Boss and His Shrink
The combo of the pairing of Robert De Niro and Billy Crystal with director Harold Ramis was a massive hit as it played to the strength of its leads. De Niro plays a mob boss who goes into therapy in what was one of Ramis’ last great films. Think this sounds similar to The Sopranos? Well, The Sopranos premiered just two months earlier and Analyze This was being filmed around the same time as The Sopranos first season. Happy coincidence, but the film was a standout among a huge year in 1999.
American Pie A Taste of Forbidden Fruit
The surprise hit of the summer of 1999 came from a film that was originally pitched by screenwriter Adam Hertz as “Untitled Teenage Sex Comedy That Can Be Made For Under $10 Million…” What he and the Weitz brothers actually delivered was an update on the ‘80s teen sex comedy that has a core of sweetness behind the MILF-hunting and dessert-humping. Jason Biggs plays the likable dork who, along with his classmates, make a pact to pop his cherry by prom, although it’s a rather more forbidden fruit that sticks with your memories. Soon it’s easy to see, the boys have much to learn. The cast is full of standout scene-stealers, from Jim’s well-meaning dad (Eugene Levy) and the sex-crazed Stifler (Sean William Scott) to flute-toting nerd Michelle (Alyson Hannigan) and The Shermanator (Chris Owen), together they nail the comedy and the true nature of school in the late ‘90s.
Bowfinger Can Martin and Murphy agree to make their film, Chubby Rain
Bowfinger, although a solid hit in 1999, is often forgotten about when critics and fans talk about the great Hollywood comedies. Which is sad, because Bowfinger has such a wonderful concept; producer Bobby Bowfinger (Steve Martin) wants to make a movie with eccentric superstar Kit Ramsey (Eddie Murphy), who wants nothing to do with the project, which is entitled Chubby Rain. (I’m not sure why that title would bother him.) But this doesn’t stop Bobby, undaunted, Bobby hatches a plan, telling the rest of the cast that Kit is doing the film but is such a method actor that he’s going to stay in character, which will require them to go up to the unaware Kit in real life and deliver their lines, all the while Bobby captures the interactions on camera. This may be a terrible way to make a movie, but the results are a fantastically hilarious comedy about the paranoia, delusion and ego that can sometimes power show business.
Life Lawrence and Murphy enjoy a 60-year vacation on a Mississippi prison farm
What starts as a 1930s gangster caper, quickly becomes a broad prison comedy about two black men who couldn’t be more different in personality than motor-mouthed con-man Ray (Murphy) and grouchy would-be bank clerk Claude (Lawrence) who are flung together by cruel chance and Southern racism. Stuck together for life by the results of a trumped up murder charge, they enjoy a 60-year vacation on a Mississippi prison farm, where their habitual ‘odd couple’ antagonism disguises a grudging respect for one another that only deepens with time. Director Ted Demme soft pedals the harshness of the prison regime, with grueling work leavened with ribaldry, baseball, barbecues and conjugal visits. However, the tone slowly darkens, as the years of false imprisonment, failed escapes and frustration over lost dreams take their toll. At times the film seems to echo the masterpiece of The Shawshank Redemption, but overall Demme has a much different approach to his characters story arcs. In the end, the feel good finale is signposted, but the restrained performances still convey a powerful sense of dignity in the face of hardship and injustice. By the way, I’m getting a little hungry. “You gonna eat your cornbread?”
Three Kings What is waiting for Clooney, Wahlberg and Ice Cube at the end of their journey is not gold, frankincense and myrrh.
Indie director David O. Russell, making his first major studio movie with Three Kings, found that having a bigger budget also meant more pressure to perform. Apparently this pressure was so great that it would lead to blows between him and leading man George Clooney. Russell and Clooney both admit to rumors of an onset scrap, though they would disagree on the circumstances. Somehow, despite the drama on set, Three Kings goes on to become one of 1999’s finest films. Set during the Persian Gulf War, the movie follows a group of soldiers who find a treasure map, leading them to conduct a gold heist during the 1991 Iraqi uprising against Saddam Hussein. It’s Russell’s masterful mix of comedy, drama and action, that helps him double his budget at the box office, and successfully announced himself as a major talent.
Varsity Blues The movie that bites back at our national sport…
Varsity Blues has all the signature trappings of the typical football movie; a tragic injury, the goofy linebacker, and the Big Final Game. However, it also bites back at what has become the national sport. Case in point, once backup quarterback now reluctant star quarterback Mox’s surly statement drawled towards his father; “I don’t want your life.” Sure, it’s an iconic line, but it also summarizes what makes Varsity Blues different from the typical sports movie. In that it mostly derides the idea that high school stardom means much of anything. Yes, the climax of the film does feature Mox leading the team to victory, but he reveals in a voiceover that he never played football again afterwards, and furthermore happily went to college a non-athlete. To add to the non-stereotypical notes, the movie’s coach does not inspire, in fact, he’s more of a villain, and the hero worship of the town is short-sighted at best, and not remotely inspiring. Despite all of this, Varsity Blues is a worthy inclusion into the best of the Class of ‘99.
South Park: Bigger, Longer & Uncut It’s okay to Blame Canada!
Trey Parker and Matt Stone’s cartoon South Park was still in its first season when in January of 1998 they started work on Bigger, Longer & Uncut. The movie remains the only full-length film to date for Stan, Kyle, Kenny and Cartman. Without a doubt, the show’s two-dimensional animation has since become far more sophisticated, but this was the perfect early example of the savvy mindset of Parker and Stone as they riff on the controversy around the show and the dangers of censorship. But of course someone has to be blamed for the kids incessant swearing, and that is where Canada’s Terrance and Phillip’s latest movie comes into play. Flush with magnificent Broadway-style musical numbers, including the Academy Award nominated “Blame Canada’, the movie grossed $83 million worldwide. Unlikely to ever see a sequel, the first South Park movie is a potent enough inclusion into the Class of ‘99.
10 Things I Hate About You Bogey Lowenstein’s Party
10 Things I Hate About You is the magnificent result of the blending together of twisty high school romance and Shakespeare’s The Taming of the Shrew. Combining a late ‘90s post-riot grrrl soundtrack and the perfect cast of young actors, including Julia Stiles, Heath Ledger and Joseph Gordon-Levitt, the film is absolutely stunning. And no Bianca, as it turns out, Bogey Lowenstein’s party was not normal, but it was classic. Julia Stiles danced on a table to “Hypnotize”, Andrew Keegan mansplained modeling, Gordon-Levitt’s Cameron got back in the game, and Ledger’s Patrick Verona and Stiles’s Kat Stratford actually fell in love. The one problem, he’s being paid to date her so that two other guys can attempt to date her sister. Yes, I agree, their dad has some strange rules. Altogether the film was a launch pad for the talents of Stiles, Ledger and Gordon-Levitt, and a solid inclusion in the Class of ‘99.
Any Given Sunday I’ll take Foxx’s Willie Beamen as my quarterback in Fantasy Football, well, Any Given Sunday
In 1999, Oliver Stone released this hyperkinetic, ultra-violent football epic to a largely unsuspecting audience. And within its nearly three hours of runtime, restored America’s sport to its skull-rattling essence. Any Given Sunday is a glorious film, but certainly not for the feint of heart, I mean a guy loses an eyeball. Take today’s football, with all the concussions and jaw-dropping hits and add some extra caffeine, and you have this movie with standout performances from Jamie Foxx, LL Cool J, Al Pacino, James Woods and Cameron Diaz. As an avid football fan, I have seen the rise of the black quarterback. I have been blessed to see the legends of Donovan McNabb and Steve McNair to today’s phenoms like Lamar Jackson, Jalen Hurts and Kyler Murray, but I think it is notable that fictional quarterback Willie Beamen (Foxx) possibly did just as much to push the black quarterback who makes plays with his legs into our living room every Sunday as any real-life player. And we are all the better for it.
Blast from the Past Adam and Eve get into the Swing of things…
Director Hugh Wilson’s Blast From the Past is a pleasantly plastic romantic comedy that finds Brendan Fraser playing a 35-year-old named Adam who’s led a sheltered life, specifically bomb sheltered. He grew up in a bunker as a result of his mad-scientist father (Christopher Walken, who else) mistaken a plane crash for a missile hit in 1962. Alicia Silverstone is Eve, the tough cookie who must wise Adam up to the ways of the largely uncouth generation upon his accent to late ‘90s Los Angeles. Will our Adam and Eve fall in love? Clearly, yes.
The Iron Giant The Tin Man has heart…
Brad Bird’s The Iron Giant, his directorial debut, was not a box-office success upon its release. I mean, on the surface, it doesn’t have the components to be a mainstream animated commercial hit, with its 1950s Cold War setting and the lack of a funny sidekick or catchy music, but the standing of the film has continued to grow exponentially over time. Bird is successful in evoking the paranoia of the ‘50s’ real world and genre preoccupations in the movie loosely adapted from the Ted Hughes book of the same name. At the heart, you will find this to be a ‘boy and his dog story’ only in this case, the dog happens to be a 50-foot robot created as a weapon. Tissues nearby will be necessary as your eyes are sure to produce moisture when the scrapheap-bound behemoth has his Superman moment. Notable here is the extremely touching voice work from Vin Diesel.
Man on the Moon Jim & Andy…
In 2017, the excellent documentary Jim & Andy: The Great Beyond chronicled how obsessively Jim Carrey channeled Andy Kaufman for Man on the Moon, the inspired biopic of the late comic provocateur. In short, upon watching, you will notice Carrey drove everyone on the set nuts. But the results of the movie speak for themselves; the film is supremely funny and entertaining as it comments on the restless artist who kept inventing and even reinventing, as he stretched comedic premises as far as he could without breaking them. A strong nod to the life of the beloved Andy Kaufman.
Galaxy Quest The tagline for this 1999 film should have been: In space, everyone will hear you laugh…
Want to know how incredibly funny and good this Star Trek spoof is, ask the actors who were the blunt of the parody. “No one laughed louder and longer in the cinema than I did,” exclaimed Patrick Stewart. William Shatner, George Takei and Will Wheaton would also join the hearty chorus of approval for director Dean Parisot’s spot on spoof of the beloved franchise. Tim Allen is Jason Nesmith, the Shatner stand-in recruited by aliens to lead an intergalactic battle. As in the show it parodies, the strength is in the ensemble cast; Sigourney Weaver plays delightfully against type and Alan Rickman brought immeasurable depth and richness to the Shakespearean thespian turned pseudo-Spock, Alexander Dane. But the standout performance might just be Sam Rockwell as he is hysterical as the expendable redshirt Guy. Beam yourself aboard for this crowd-pleasing adventure and you will not be disappointed.
Being John Malkovich It’s the Malkovich Point of View…
Charlie Kaufman has really weird movie ideas. The screenwriter’s debut, Being John Malkovich, imagines a portal that can send average people into the mind of celebrated actor John Malkovich. The movie was also the debut for director Spike Jonze, who brought the surreal and hilarious idea to vivid screen life. First time viewers should be on the look out for the incredible Charlie Sheen cameo.
Election Tracy Flick for Class President
On record, director Alexander Payne has said “I always thought we were just making a nice little comedy with some realistic and hilarious characters” in regard to his adaptation of the Tom Perrotta novel. So you can imagine his surprise later when many in the audience saw it as a political metaphor. Whether you wade deep in the waters or not, what’s certain is Election, in its depiction of a blood-thirsty high school class presidential election speaks to something profound about America’s competitive political landscape. This is one of Reese Witherspoon’s funniest roles and Matthew Broderick is near perfection as the mediocre middle-aged teacher determined to ensure she loses. Recently garnering acclaim for last year’s The Holdovers, Payne’s Election standouts as a wonderful candidate in the Class of ‘99.
Office Space Your career path could be an occupational hazard…
Do you feel you’re like raging against the men in your daily drudge of annoying colleagues, asinine company rules, and brain-numbing tasks? If so, Mike Judge’s satire on corporate America is for you. Akin to many a cult comedies, Office Space did not find box office success, but certainly found its audience via the video store, as McJobbers discovered and found camaraderie in IT desk slave Peter (Ron Livingston) who turns workplace renegade after a hypnotherapy session leaves him immune to the stress of the office and its responsibilities. As a precursor to The Office and Horrible Bosses, Office Space expertly maps the petty peeves of cubicle life; missing staplers, pointless form-filling, the idiots in charge of ‘restructures’, and did so by tapping into a rich comic vein of a universally recognizable experience, whether your blue collar or white collar. “Putting new cover sheets on all the TPS reports before they go out now” is funny because it’s true.
Go A Doug Liman Christmas…
It’s true that Doug Liman’s directing debut Swingers is largely viewed as a Jon Favreau film, as writer, Favreau, would clearly become synonymous with the movie. But Go would go on to establish and solidify the filmmaking talent that Liman would become. The film is a funny, thrilling Tarantino-like look at a group of diverse characters set around Christmas, launching the careers of Sarah Polley and Dawson’s Creek alum, Katie Holmes, it sends audiences on a drug and crime infused ride.
There you have it. James Bond parodies, delicious rom-coms, Canada blame. These were 20 of the films that made 1999 the best movie year ever.
