23 movies that highlight why 1999 was peak cinema
The fear of Y2K must have caused a sense of urgency at the end of the 20th century because everything was cranked up to an eleven. Boy bands were synchronized dancing into the hearts of teens and tweens across the globe, The Sopranos ushered in the beloved anti-hero long before Taylor Swift became a household name, and movies were, well, the best they’d ever be. Yes, technology has taken the world of film far, and companies like A24 have pushed the boundaries of creativity, but alas, the following will more than prove that 1999 was the best year for movies — ever.
'10 Things I Hate About You'
Were there a few too many teen movies that revolved around one student trying to make another student seem popular or accepted by their peers? Of course, but if it ain’t broke, don’t fix it, and 10 Things I Hate About You was far from having a crack in its glorious armor that paired Julia Stiles with Heath Ledger. It also featured one of the best uses of a Notorious B.I.G. song to ever be in film.
'American Pie'
American Pie picked up from where movies like Porky’s and Fast Times at Ridgemont High left off but elevated the raunch in a whole new way with this one time at band camp and the infamous pie scene being launched into the zeitgeist forever.
'Big Daddy'
Adam Sandler’s comedies would take a hit in the new millennium with the likes of That’s My Boy and Jack and Jill, with the focus being geared more towards his dramatic works. However, before that script was flipped, Big Daddy became one of his best movies that packed in as much heart as it did comedy.
'Boys Don't Cry'
Hilary Swank had to have known an Oscar nomination was in her future when she read the script for Boys Don’t Cry, and she likely knew she would win as soon as the film wrapped because that was a performance that actors could only hope to have in their lifetime.
'But I'm a Cheerleader'
In 1999, the LGBTQ representation in media was slim to none, so a movie that focused on the idiocy of conversion camps that paired a real-life message with a lesbian storyline was not something people saw every week in theaters. Groundbreaking and a delight, it’s one of Natasha Lyonne’s signature roles to this day.
'Dogma'
Religion isn’t the easiest subject matter to tackle, especially when making it funny. Thankfully, writer and director Kevin Smith came along and was able to intertwine higher beliefs with an earnest yet comedic cast that included Chris Rock, Ben Affleck, and Salma Hayek.
'Fight Club'
There was something to be written about this, but the first rule wasn’t something anyone wanted to break.
'Galaxy Quest'
Moviegoers might not know what to do with a movie like Galaxy Quest today since it’s rare for silly comedies to fare well in theaters or not be destined for a streaming debut.
'Girl, Interrupted'
Is there a genuine reason as to why Angelina Jolie and Winona Ryder have not teamed up again? They were electric together in Girl, Interrupted.
'Idle Hands'
Devon Sawa has cemented himself in pop culture in a number of ways. He was a Tiger Beat dream come true in the ‘90s in movies like The Little Giants and Casper, gave a face to the term “Stan,” and, of course, he starred in a now Halloween cult classic, Idle Hands.
'Man on the Moon'
Jim Carrey dominated the ‘90s as one of the most beloved comedic actors, then decided to head in a whole new direction at the end of the decade. Man on the Moon launched him into new heights and made everyone realize he had more up his sleeve than just a talking butt routine.
'Never Been Kissed'
Drew Barrymore has been acting since she could walk on set, and it shows. She dominates everything she touches and has so many notable moments in her career, but is it safe to say that her signature role came about in 1999 when she played a journalist who heads back to high school for a story, only to wind up not only facing her past trauma as a social leper but finding love along the way?
'Office Space'
Before The Office (and Jim Halpert) preached the mundane ways of a 9-to-5 in an office setting, there was Office Space.
'She's All That'
She’s All That is the reason a whole generation still laughs when people think removing someone’s glasses can automatically turn their world around.
'Star Wars: Episode One - The Phantom Menace'
The Phantom Menace got a lot of hate when it came out, and it was aimed at everything from the literal child who starred in the film to the fictional character Jar Jar Binks. However, in hindsight, this movie was not that bad and was actually a great jumping-off point for everything that followed, helping expand the Star Wars universe.
'Tarzan'
Phil Collins’ soundtrack for Tarzan elevated the movie, and honestly, he didn’t have to go that hard for a movie about a man who was raised by gorillas.
'The Blair Witch Project'
In many ways, The Blair Witch Project’s marketing was the first viral moment. The mystery surrounding the release and the story was addicting for many and helped kickstart the found footage genre in horror.
'The Iron Giant'
Animated movies rarely get the level of respect they deserve, but that is where The Iron Giant differs because it was revered from the start and, to this day, one of the most respected animated films in history.
'The Matrix'
What would fight scenes be like in cinema without the influence of The Matrix? Exactly.
'The Mummy'
The Mummy was a sexual revelation for an entire generation, thanks to Brendan Fraser, Rachel Weisz, and Arnold Vosloo.
'The Sixth Sense'
It was the twist of the year, decade, and century that absolutely no one saw coming. It’s also the twist that every movie made since has been chasing.
'The Virgin Suicides'
Director Sofia Coppola left no crumbs when it came to adapting Jeffrey Eugenides’ debut novel for, ironically, her debut film behind the wheel.
'Zenon: Girl of the 21st Century'
Disney Channel Original Movies used to be monthly moments, and one of the GOATs will forever be the futuristic ways of Zenon: Girl of the 21st Century.
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