Photo: Warner Bros.
The end of the 20th Century brought bucket hats, Napster introducing illegal ways to share and download music like a little “Mambo No. 5,” and the hilarious Y2K panic. Most importantly, 1999 debuted some of the best films of its decade, offering a big turning point for cinema with lots of firsts that kicked off innovative comedies, horror movies, teen angst films, and a few cerebral experiences.
To celebrate, we gathered a few of Mandatory’s Best 20th Anniversary Films being commemorated this year.
Ranked: 11 Must-See Black History Month Movies
Around the corner: Where to Stream 2019 Oscar-Nominated Movies
Follow Mandatory on Facebook, Twitter, and Instagram.
20 Year Films
-
'The Matrix'
Our favorite mind-bending (and spoon-bending) movie centers on reality and the war against who controls reality. Walking away with four Oscars, The Matrix inspired a multitude of conversations over whether you would have taken the red pill or the blue pill. Despite starring in plenty of popular roles, Keanu Reeves will forever be known as Neo, (aka "The One") thanks to the Wachowski's game-changing sci-fi movie.
-
'The Sixth Sense'
"I see dead people" might be one of the most quoted and parodied lines of all-time. The Sixth Sense earned innovative writer-director M. Night Shyamalan Oscar nominations for what still holds up as one of the best horror dramas produced. Commanding performances, a fresh narrative, visually striking storytelling, and one hell of a twist ending made Shyamalan's horror feature debut unforgettable.
-
'Office Space'
Mike Judge's satirical look at the occupational crises felt by a group of friends at a '90s software company may have flopped at the box office, but over time fans turned it into a cult classic. Even now, Office Space is considered one of the most relatable workplace comedies ever, helping those who have ever fantasized about destroying office equipment to laugh it off instead of actually setting any buildings on fire.
-
'Fight Club'
The first rule of Fight Club is that you do not talk about Fight Club, but we're a fan of breaking rules. David Fincher's Oscar-nominated adaptation of Chuck Palahniuk's novel is still as controversial as it is thought-provoking 20 years later. Audiences either love or hate this movie. Some left with an aftertaste of sexism and toxic masculinity at its worst, others were inspired by the idea of living life with total abandon.
The movie is full of themes (i.e. consumerism, trauma, fascism) that fans have analyzed for two decades. No matter what your experience with this film, there's no denying it made an impact partly in thanks to Brad Pitt and Edward Norton's stellar performances.
-
'The Blair Witch Project'
Paranormal Activity may be the first movie that comes to mind when people today think of found-footage horror, but The Blair Witch Project put the genre on the mainstream map. Thanks to brilliant marketing (including leading people to believe that the film contained "real" evidence of a paranormal entity), the film made about $250 million at the box office, becoming one of the most successful independent movies ever.
-
'Star Wars: Episode I - The Phantom Menace'
The prequel trilogy of the Star Wars movie franchise took fans even further back into the past to a young Obi-Wan Kenobi and baby Anakin Skywalker before he turned to the dark side and became Darth Vader. Despite smashing the box office and earning three Oscar nominations, the film faced some harsh backlash (it's been 20 years, time to let that Jar Jar rage go) leaving fans disagreeing over how the initial origin story was handled. Ewan McGregor, the podrace, and the film's final act were definitely highlights.
-
'Austin Powers: The Spy Who Shagged Me'
Mike Myers reprised his groovy role in the spy action-comedy sequel, which, much like its predecessor, parodied other movies such as James Bond features. The comedy's ability to make fun of itself on top of supplying memorable pop culture characters like Dr. Evil made the trilogy irresistible to audiences. The Spy Who Shagged Me was even nominated for Best Makeup at the 2000 Oscars.
Mike Myers has supposedly been brainstorming about a possible fourth installment in the Austin Powers franchise, but after 20 years, it might be better to leave the character in the past.
-
'Man on the Moon'
In Man on the Moon, Jim Carrey stars as the late Andy Kaufman, who was considered one of the most innovative, eccentric, and enigmatic performers of his time. A master at manipulating audiences, Kaufman specialized in creating performances so real that even his close friends were never sure where the truth lay.
Carrey won a Golden Globe for his performance as Kaufman and later explored the journey of immersing himself into the role in Netflix's documentary Jim & Andy: The Great Beyond, featuring over 100 hours of previously unreleased footage from the movie's set.
-
'The Green Mile'
Not every Stephen King adaptation hits the mark (see: Graveyard Shift, Thinner, Dreamcatcher, etc.) but The Green Mile, adapted by Frank Darabont and starring Tom Hanks and Michael Clarke Duncan, more than exceeded expectations. Exploring the struggle between good and evil, the four-time Oscar-nominated movie offers a heavy insight into the value of life.
-
'10 Things I Hate About You'
In one of the many teen angst comedies that exploded out of the late '90s, 10 Things I Hate About You (based on Shakespeare's The Taming of the Shrew) starred Julia Stiles and the late Heath Ledger in a clever, mostly fun coming-of-age tale of high school, popularity, individualism, trust issues, forced love, genuine love, and everything in between.
-
'American Beauty'
The disgraced Kevin Spacey, who now spends his time going to court over felony charges for alleged sexual assault, once starred in this Oscar-winning drama following a sexually frustrated suburban father who has a mid-life crisis after becoming infatuated with his daughter's best friend. Yikes. The movie, once acclaimed for its dark wit and strong overall performances, now feels hollow and, frankly, creepier.
-
'Cruel Intentions'
Sarah Michelle Gellar and Ryan Phillippe star as seductive, manipulative step-siblings who enter into a bet to deflower Annette (Reese Witherspoon), daughter of the headmaster at their school, before the end of summer break. On the line is a vintage 1959 Jaguar Roadster and the step-siblings hooking up. Yes, you read that correctly.
The dark drama romance layered in themes of sex, power, revenge, drug abuse, a quasi-incestuous relationship, true love, and death, received mixed reviews when it first premiered. It was a box office hit, however, earning $75 million from a $10.5 million budget and encouraging sequels that we don't talk about.
-
'American Pie'
It's a tale as old as time: four teenage boys enter a pact to lose their virginity by prom night, leading to raunchy hilarity and over-the-top shenanigans. The sex comedy earned a whopping $235 million at the box office and remains one of the best (and most ridiculous) teen movies of its generation.
-
'Varsity Blues'
In Varsity Blues, the late Paul Walker and James Van Der Beek star as high school quarterbacks. The comedy-drama follows the high school football team and their overbearing coach as the players deal with the pressures of adolescence on top of their football-obsessed community.
Varsity Blues is often overshadowed by Friday Night Lights (both the movie and the incredibly popular TV series) but it deserves to stand on its own merits. The movie's sub-theme of "boys will be boys" doesn't do it any favors, though.
-
'She's All That'
She's All That offered enough comedy and romance for the charming leads (Freddie Prinze Jr., Rachael Leigh Cook) to play off of, so much so that it became of the most popular teen movies of the decade. The largely predictable movie isn't without its flaws, such as playing into the old trope of turning the "ugly duckling" girl into a "beautiful swan" to make her more socially acceptable. The movie has a few redeemable qualities, however, and it fits rather well into the '90s teen angst era.
