5 ’90s Movie Masterpieces That Just Keep Getting Better

5 ’90s Movie Masterpieces That Just Keep Getting Better

One of the best things about the ’90s is undoubtedly the cinematic triumphs that arose throughout the decade. It’s hard to believe that it’s been over 30 years since some of these movies came out. Whole generations have been born in the meantime, and yet, for some, this feels almost like yesterday. From the advances in animation and the launching or return of fan-favorite franchises to the rise of stars that we still consider among the best today, the decade was truly revolutionary.

Thus, we’ve compiled a list of several ’90s flicks that just keep getting better. With so many great ’90s movies out there, it’s tough to narrow down just five for a list of movie masterpieces. There’s no doubt that there are hundreds of different movie combinations that could easily fit under this prompt, but for this author, these five stand out most. Be it their rewatchability, cinematic artistry, unrivaled performances, or emotional resonance, these five movies are among the best to ever make it out of the ’90s — and they continue to get better with age.

‘Groundhog Day’ (1993)

Bill Murray as Phil Connors driving a car while holding a groundhog in Groundhog Day (1993)
Image via Columbia Pictures

When it comes to ’90s comedies, there may be few that you rewatch every year, but Groundhog Day could easily be an exception to the rule. It’s in the name, of course: every February 2nd, this flick becomes more relevant as Bill Murray‘s weatherman Phil Connors is stuck in the time loop of the century. Although not actually filmed in the real Punxsutawney, Pennsylvania (it’s actually Woodstock, Illinois), Groundhog Day has become as synonymous with the annual tradition as the groundhog itself — and for good reason.

In an age where comedies are super hit-or-miss, Groundhog Day is a reminder that endlessly rewatchable comedy is a real gift. As Murray relives the same day over and over, we not only relive the same jokes but also find that he can play the scene in a plethora of memorable ways, each as important as the last. It’s a bit screwball at times, and if you were to watch it one day from the perspective of the rest of the cast, you might think that Phil is just a crazy person. That’s part of the charm of the Harold Ramis film that just keeps getting better.

‘Tombstone’ (1993)

Doc Holliday, Virgil Earp, Wyatt Earp, and Morgan Earp walk side by side in Tombstone.
Doc Holliday, Virgil Earp, Wyatt Earp, and Morgan Earp walk side by side in Tombstone.
Image via Buena Vista Pictures

The ’90s were a great time for Western fans or those looking to get into the genre. After some award-winning Westerns at the start of the decade, audiences were floored with the action-packed horse opera that has become a genuine favorite among genre enthusiasts and casual visitors alike: Tombstone. Despite all the glaring production issues that threatened to kill the film before it could be completed, the efforts of the cast and crew, rallying behind star Kurt Russell, turned Tombstone into a ’90s triumph that only gets better with age.

It’s hard to compete with Tombstone for all its pulse-pounding Western action and the thrilling performances of its leading stars, namely the late Val Kilmer, who elevates himself to another level in a career-defining performance that could not have been achieved by another. Although not so critically acclaimed as Dances with Wolves or Unforgiven, which each won the Oscar for Best Picture in the early ’90s, Tombstone continues to delight and defy expectations with each viewing.

‘Heat’ (1995)

Although both Al Pacino and Robert De Niro had already established themselves as notable crime picture giants, Heat put them together on the big screen for the very first time (no, The Godfather, Part II doesn’t count). Directed by Michael Mann in an effort to remake his failed efforts for the story previously explored in L.A. Takedown, the picture expertly balances its two opposing leads as Pacino’s Vincent Hanna and De Niro’s Neil McCauley circle one another with powerful ability. As one of the most stylish crime thrillers, Heat elevates its leading men above the (also impressive) action by adding personal, private stakes to their already massive professional ones.

As with Tombstone, Val Kilmer offers some of his best career work here, though his part as Chris Shiherlis isn’t as lovable. Truly a crime masterpiece, Heat is Mann’s magnum opus that stands as one of the best (and most underrated) pictures of the decade. The thoughtful script is enhanced by the gravitas of Pacino and De Niro, who make Mann’s words appear almost as Shakespeare with guns and shootouts. Each watch only reinforces its effectiveness as a thrilling detective/crime picture.

‘Terminator 2: Judgment Day’ (1991)

The T-800 aiming a rifle while John Connor sits in front of him in Terminator 2: Judgment Day
The T-800 aiming a rifle while John Connor sits in front of him in Terminator 2: Judgment Day
Image via Tri-Star Pictures

Arguably the best action movie of all time, Terminator 2: Judgment Day takes everything audiences thought they knew about The Terminator after James Cameron‘s original outing and embellishes it with a subversive style. After playing the villain in the original, Arnold Schwarzenegger is back with his biker look and scowling features to play an action hero who somehow develops an almost fatherly bond with the very boy whom his kind were created to terminate. Likewise, Linda Hamilton has learned from her previous experience, transforming herself into an action hero for the ages with layers of trauma and plenty of motivation to see things through.

Although the technology may seem dated today, Cameron pioneered computer-generated imagery for T2 that set the standard for what was to come. The liquid T-1000 (Robert Patrick) still looks incredible, and the action is so top-notch it’s no wonder that Cameron still considers it some of his most dangerous stunt work to date. With genuinely compelling character arcs, riveting action, and a definitive ending that perfectly bookends the story Cameron had begun nearly a decade earlier, Terminator 2: Judgment Day does everything right. In a world where sequels are a dime a dozen, this one proves that sometimes they can be superior to the original.

‘The Iron Giant’ (1999)

Hogarth sits on the ground in the woods as the Iron Giant crouches down to speak to him in The Iron Giant.
Hogarth sits on the ground in the woods as the Iron Giant crouches down to speak to him in The Iron Giant.
Image via Warner Bros. Pictures

Compared to many of the animated films seen today, there’s something about The Iron Giant that remains timeless despite the ’50s setting. Brad Bird‘s directorial debut is a masterful animated feature that appeals to all ages for its unique take on the coming-of-age story mixed with Cold War paranoia, classic sci-fi wonder, and the notion of what heroism truly means — something that has always spoken to me since my youth. Everything we love about the traditional hero’s journey and the complicated nature of growing up is found here in a film that stands apart as a one-and-done adventure full of more heart than a dozen made-for-kids features today.

The Iron Giant is not just brilliant on an emotional level, but technically as well. With a tight script and an alternate Signature Edition cut that restores one of the most important deleted scenes, there is so much about this 1999 animated achievement that audiences only appreciate more as time goes on. From the 2D animation to the incredible voice cast — which includes Vin Diesel, Eli Marienthal, Jennifer Aniston, Harry Connick Jr., and Christopher McDonald — Bird proved himself a man of exceptional talent and vision with his very first outing, one that continues to soar miles higher than most similar features made today.

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