23 movies that highlight why 1999 was peak cinema

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 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.

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.

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.

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.

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.

There was something to be written about this, but the first rule wasn’t something anyone wanted to break.

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.

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.

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.

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.

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?

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 is the reason a whole generation still laughs when people think removing someone’s glasses can automatically turn their world around.

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.

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.

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.

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.

What would fight scenes be like in cinema without the influence of The Matrix? Exactly.

The Mummy was a sexual revelation for an entire generation, thanks to Brendan Fraser, Rachel Weisz, and Arnold Vosloo.

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.

Director Sofia Coppola left no crumbs when it came to adapting Jeffrey Eugenides’ debut novel for, ironically, her debut film behind the wheel.

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.