Reeves’ breakout role, few films serve as great an introduction as cult-classic Bill & Ted’s Excellent Adventure. The film centers around the titular Bill (Bill S. Preston, Esq. played by Alex Winter) & Ted (Ted Theodore Logan, played by Reeves), two highschool deadbeats living average lives in San Dimas, California. Unbeknownst to our protagonist duo, their yet-to-be formed band, the Wyld Stallynz, happens to create the greatest record in human history in the somewhat near future, aligning the planets and ushering in universal harmony. Yet, the entire future is at stake if Bill & Ted don’t manage to ace their upcoming history test. Thankfully, Rufus (George Carlin) arrives from 2688 in a time traveling phone booth in order to help the future rock gods travel back in time and retrieve historical figures of the most triumphant importance in order to wow their skeptical teacher. Aside from inspiring countless catchphrases—”wow,” “most non-triumphant," classic air guitar noises, etc.–the film managed to encapsulate ‘80s burnouts to a tee. Reeves’ Ted, in a band tee, suit vest, smiley denim shorts over pulled up leggings and converse captures the essence of rock-obsessed teens in a way John Hughes could only dream of. The inspiration of countless Halloween costumes—and arguably DIY streetwear—Ted not only introduced Reeves as an actor to watch, but a style maverick as well.

Earning its title from surfing terminology, it’s not surprising that this film is a time capsule of early-’90s “x-treme” sport style (not to mention a few cheer-worthy clichés and quotes). Reeves takes on the role of Johnny Utah: an undercover FBI agent tasked with taking down a troupe of criminals. While the setup seems fairly mundane for modern cop films, its beachy LA backdrop sets the stage for over-the-top action and antics; Utah’s undercover operation ultimately uncovers that the gang of bank robbers he’s searching for—the “Ex-Presidents”—are actually a gang of stereotypical surfer dudes. While Reeves’ Johnny Utah begins as a buttoned up rookie cop, it’s his turn as an undercover surfrat that epitomizes his style in the film. With sun-faded T-shirts, sea salt-crusted ligthwash jeans, flowing flannels and aloha prints, just be thankful that you don’t have to become someone who can skydive (without a parachute!) to pull of these now-decade-defining looks.

After numerous blockbusters under his belt, Reeves starred in one of his most ambitious roles to date, as Scott Favor in Gus Van Sant’s critically celebrated My Own Private Idaho. Although already considered a rising star, critical success so far eluded Reeves. His work as Scott Favor changed everything. Based on a series of Shakespeare acts—lifted from sections of Henry IV and Henry V—the film follows best friends Michael “Mike” Waters (River Phoenix) and Scott Favor, two street hustlers in Portland who run various tricks for cash and drugs. Mike, who hustles out of necessity, suffers from chronic narcolepsy, passing out in various points in the film. Eventually, Mike is hired by a wealthy woman who invites him to her mansion where he encounters Scott (Reeves). After another narcoleptic attack, Mike awakens with Scott in Portland, before convincing his best friend to help him track down his mother. The two head to Idaho—hence, the title—where a sequence of events eventually push them to Italy and back. While lacking much for plot, the film plays as a fantastic character study, examining everything from drug addiction to unrequited love (Mike, a gay man, loves Scott who while straight sleeps with men for cash). When the film premiered at the Venice International Film Festival in ‘91 it not only solidified Van Sant as a creative auteur, but established both Phoenix and Reeves as dignified actors, not just Hollywood heartthrobs. Stylistically, the movie captures the sort of aimless, wandering vagrant youth designers find as a continuous source of inspiration. Scott especially, from his leather schott perfecto over a ripped hoodie, fitted black blazer over white shirt as a nod to his secret wealth and iconic brown shearling jacket is still plastered across designer moodboards. In fact, one designer in particular was so enamored with the film he dedicated an entire collection to it. Obsessed not only with the movie, but the Portland color palette and its famous weed culture, Takahiro Miyshita presented his Fall/Winter 2008 Number (N)ine collection, “My Own Private Portland.” A sartorial masterclass, Miyashita built on the grunge look pervading the film and amplified it. The breathtaking show—considered the season’s best—is ample evidence of both Phoenix & Reeves’ enduring style influence.

While cult classics like Bill & Ted and Point Break helped earn Reeves status as a cult favorite, it was his role in 1994’s Speed that cemented him as a household name. Embodying LAPD officer Jack Traven, the film earns its title for its combination of high-stakes and high-speed, as Traven and Annie Porter (played by Sandra Bullock) attempt to disarm a bomb on a bus before the vehicle dips below 50 mph—triggering the explosive and killing everyone still on board. While the film features Reeves in yet another role as a member of law enforcement, the actor’s ability to make off-duty cop style cool is something of an art form. Consisting of just one look, Reeves off-the-cuff cop vibe is simple but classic, practical but pedestrian. Consisting of khakis, a tucked-in white tee and layered, opened-up collared shirts, it’s not Reeves most groundbreaking role aesthetically—but it’s definitely the look most guys have in mind when then get ready for work in the morning. Hats off for turning something so minimal into something high octane.

In 1995, Reeves starred in one of his worst reviewed performances to date. While critically panned, Johnny Mnemonic was well ahead of its time—at least from a costume perspective. Loosely adapted from celebrated dystopian author (and noted Acronym fanatic) William Gibson’s novel of the same name, the film takes place in a dystopian future (2021) where “mnemonic couriers” receive brain implants to personally carry information deemed too sensitive to be sent through the Net, a virtual reality version of the internet. Reeves stars as the titular Johnny Mnemonic, who embarks on one last delivery to raise enough money to remove his implant and restore his childhood memories. While traveling to Beijing, Johnny is attacked by Yakuza in the midst of receiving an encryption key, ensnaring him in the midst of plot between anti-establishment rebels and the pharmaceutical company who they are fighting. While the slapdash plot and cheesy dialogue are nothing to write home about, Johnny’s wardrobe—a futuristic suit & tie combo somewhere between ‘80s Armani and peak Issey Miyake—is as good a wardrobe highlight as any. If anything, the film is simply more evidence of something that, at this point, is well established: Reeves looks damn good in a black suit.

You can debate the influence of Reeves’ other films, but there’s no debating this: When it comes to the actor’s filmography, none are more impressive or as culturally impactful as The Matrix. The skinny sunglasses and the long black clothes (not to mention all that slick leather) were so unique and emblematic at the time, the film’s title is often used as shorthand for the “new millennium”-adjacent aesthetic that we see on runways today. Ripe for both parody and earnest inspiration, the super-stylized look of Neo and company was more than just an attempt at creating kick-ass clothing—it was an intentional choice. “When we made The Matrix, we were aspiring to what the world could be, which is happening now,” costume designer Kym Barrett explained to Fashionista. With all the of the high-flying, bullet-time sequences, the protagonists of the film were effectively performing as then-modern-day superheroes, saving humankind from an existence enslaved in digital oblivion; this naturally shaped costume design—especially when it comes to those iconic duster-length trenches. “They can move in an almost gravity-defying way. They can jump across buildings; they can almost fly...I wanted to find a modern version of something that could move like a cape, so that's where the coats were born,” Barrett explained. Oh and those sunglasses, those are a character statement too. Designed by Richard Walker, those wacky, tiny shaped frames were a necessity, not just as a story device (characters with the shades represent those who know the truth about The Matrix) but as a practical reality. “They wouldn't create a pair of glasses that could fit on 500 other different people...everything was customized,” Barrett explained. For a film that was obsessed with the uncertainty of the future, it’s rather fitting that its now retro-futuristic take on “modern” fashion continues to resonate with relevance well into the 21st century.

After a string of forgettable performances, Reeves flexed his Hollywood A-List status with 2014’s John Wick. In what many considered a return to form, Reeves starred as the titular Jonathan (John) Wick, who following the death of his wife due to a chronic illness, bonds with a dog she left him as a way to heal. When a russian mobster breaks into John’s house, steals his prized '69 Mustang Mach 1 and kills his dog, John goes out seeking retribution. Revealed as a former assassin operating under the codename “Baba Yaga,” John kills countless men on his rampage, upending the entire New York-based russian syndicate (his former employer) in his wake. With little in the way of marketing, John Wick surprised both fans and critics grossing over $88 million dollars on a $20 million dollar budget, no doubt reinvigorating Reeve’s career. Positioned as a ruthless foil to James Bond, John Wick—in his dark, sharply tailored bulletproof suits—employs the sort of badass machismo that Liam Neeson used to great effect as Bryan Mills in Taken, albeit much better dressed. With the help of famed tailor Luca Mosca, whose previous creds include dressing both Harrison Ford and Gary Oldman, Reeve’s made-to-measure suits (which recently he began wearing off-screen as well, paired with hiking boots, no less), have helped transform the 54-year-old actor into a perennial star of GQ’s best dressed list. After a successful sequel, John Wick: Chapter 2, landing the cover of GQ’s May, 2019 issue and John Wick: Chapter 3 - Parabellum dethroning Avengers: Endgame at the box office this weekend, we are officially entering a new era of Keanu. Acting chops aside—of which there are plenty—if he keeps wearing suits this good, Reeves will stay a star forever.