1 / The Matrix
He’s Neo. And Neo’s the One. In 1999, Keanu made movie history in the landmark sci-fi/action film “The Matrix” from the Wachowskis. This is also where he met his stunt double Chad Stahelski, who would later go on to helm all of the John Wick films. While the subsequent “Matrix” films never quite matched the lofty transcendence of the first edition, the original still stands as an incredible genre flick. It's perfectly cast with Keanu at the center, going down the rabbit hole and emerging as a singular superhero.
2 / Bill & Ted's Excellent Trilogy
It’s the trilogy most associated with Keanu Reeves’ actual personality. But that doesn’t give him the full credit he deserves as an intelligent human being, and a well-rounded talent. This excellent trio of comedies (most represented in the first classic installment) does convey a couple of essential things about the guy. One, he’s an extremely likeable and un-self-conscious actor. And two, he does seem to care about his friends, family, and the universe at large. He embodies the film's overall mantra to "be excellent to each other…and…party on, dudes!"
3 / Speed
Keanu’s first massive box office hit was director Jan de Bont’s bus-rigged-with-a-bomb thriller "Speed." It introduced worldwide audiences to Reeves as a first-class action hero, and Sandra Bullock as a charming, witty movie star who’d survive this installment and the not-so-speedy sequel (which Reeves wisely passed on). Keanu’s Jack Traven is everything you want in the performer – he’s an earnest can-do, will-do man of physical prowess, who has an unironic sense of duty and decency.
4 / River's Edge
One of Reeves’ earliest film roles was in Tim Hunter’s classic disturbing teen murder drama “River’s Edge.” Three plus decades later, the film is still a chilling depiction of teenagers too stoned and disaffected to bother to report their friend’s murder (by another friend) to the authorities. Keanu gives a highly effective performance as teenager Matt, whose conscience eventually provokes him to do the right thing.
5 / My Own Private Idaho
Gus Van Sant’s tale about street hustlers roaming around Portland and other areas of the Northwest and the world is a colorful and ambitious indie with an incredible performance by River Phoenix as a troubled, well-meaning youth looking for a sense of home and real love. Keanu’s his best friend and companion, whose journeys through street life are more of a detour before moving on to other things. While Phoenix's performance was rightly acclaimed, Keanu also puts in a strong and confident turn that ranks among his greatest work.
6 / Parenthood
Ron Howard’s ensemble about the ups and downs of daily life for a multi-generational family is a showcase for all the performers, and Keanu’s no exception. His Tod is definitely a bit of an airhead, but one who has a sensitive and surprisingly wise heart underneath it all.
7 / Toy Story 4
As with the live-action "Parenthood," Pixar's most recent "Toy Story" entry features a stellar all-star cast. Not to take away from franchise stalwarts Tom Hanks and Tim Allen, but we love Keanu Reeves most in this fourth installment. He's the newcomer, a Canadian daredevil stuntman motorcyclist named Duke Kaboom. Often clueless about the limits of his stunt-riding prowess, Duke's also eternally endearing with his genuine likeability – just like the guy behind him.
8 / Permanent Record
No less a film critic than Roger Ebert declared the underseen and underrated "Permanent Record" as one of the very best films released in 1988. The story about a teen suicide packs an emotional wallop, and much of its impact comes from Keanu’s realistic portrayal of the best friend left behind. Imagine Ted "Theodore" Logan without his buddy Bill, in a straight drama that’s genuinely heartbreaking. While that might sound strange, Keanu makes it all work perfectly.
9 / Point Break
It’s such a popular Keanu Reeves title that it's also become an interactive live performance where someone in the audience is selected to play Reeves' undercover cop Johnny Utah. Maybe that means that anyone can sub in for the token "blank" everyman. Or maybe it just means that Reeves is the perfect "everyman." Either way, he looks great, and director Katherine Bigelow whips up an action classic that combines gunfights, fistfights, skydiving, surfing and one of the all-time memorable foot chases in Hollywood history. Plus…all hail the late Patrick Swayze's ever-wise surfer-skydiver-bank robber-guru, Bodhi.
10 / John Wick: Chapter 3 – Parabellum
The third time's still the charm in the action blockbuster series known as "John Wick." In this chapter, the unstoppable force that is Keanu's assassin John Wick is on the run from what seems like all of the world's top killers after taking down a member of the High Table in Chapter 2. While we've seen this type of action before in the other entries, Reeves and the filmmakers continue to up the ante with ever-more creative sequences...and we still always feel for the soulful hero at its center.
11 / Dangerous Liaisons
His part is small, but it’s still critical to the overall artistry at work in Stephen Frears’ decadent re-telling of “Les Illaisons dangeruses.” Acting titans John Malkovich and Glenn Close are the two main players using their wiles and skills to manipulate the lives and romances of unsuspecting royals Uma Thurman and Michelle Pfeiffer. Reeves is mostly on standby as the simple music teacher that Thurman favors. But he’s also nearly the only dignified one present at the proceedings. Interesting to note: this costume period piece played in theaters at the same time as the first Bill & Ted’s movie - two great Reeves movies at opposite ends of the spectrum.
12 / John Wick: Chapter 2
The first John Wick movie set the table. The second heartily breaks it into a million pieces, as John Wick’s world grows ever larger, as do the stakes and body count. His "Matrix" co-star Laurence Fishburne makes a return as underground crime lord and Wick advocate The Bowery King, as do most of the remaining players from the first installment (Ian McShane, Lance Reddick, John Leguizamo, etc.).
13 / A Scanner Darkly
What do you get when you combine amazing rotoscope animation, source material from the creator of "Blade Runner," the director of "Dazed and Confused" and "School of Rock," the leading star of the Marvel Cinematic Universe, and our hero and savior from "The Matrix"? You get this underrated gem about an undercover police officer who spends his nights scoring drugs, seeking informants and sources, and inching ever closer to becoming a dangerous felon.
14 / John Wick
The first John Wick set the template for the series. It also revealed the greatest attributes of our hero. He is a man of believable physical action, and he acts out against forces of badness because of the pain he’s experienced. It wasn’t just that they killed his dog. It was what the dog represented…a gift of hope, from his wife who died, and whom he truly loved. John Wick is a bad man who wanted to turn a corner. When that place is taken away from him…the result is an avenging act…and a landmark genre film.
15 / The Night Before
You might think that Ted "Theodore" Logan is the greatest distillation of Keanu at his loveable, goofy best. But Ted has some serious competition from Winston Connelly. Even better, unlike a lot of Keanu’s mid-late ‘80s output, Winston’s not a loveable stoner. He’s a loveable geek. And as always with Reeves, he’s a geek with a quirky nature and an unmistakable decent streak. Here, it’s up to Keanu to save his prom date Tara Mitchell (Lori Loughlin) after they get lost in East LA and she’s kidnapped by pimps. It’s a fun '80s romp with Reeves in full command of his eccentric, comic persona.
16 / Bram Stoker's Dracula
It has its critics, but Francis Ford Coppola’s baroque version of "Bram Stoker’s Dracula" is an A-plus production, with moody visuals and varying performances (including a wide-eyed Keanu and an over-the-top Anthony Hopkins…to say nothing of Gary Oldman’s committed take on the title role). It all adds up to a highly intoxicating and entertaining period horror-thriller.
17 / The Replacements
One of Keanu’s most watchable films is this winning sports comedy about scrubs who get a chance for redemption when the pro football players all go on strike. Keanu Reeves as down-on-his-luck former star quarterback Shane Falco is perfect casting. He’s the underdog you want to root for – leading a team of equally worthy underdogs who’ve earned and deserve their time in the spotlight.
18 / A Walk in the Clouds
An underrated and wistful period love story, "A Walk in the Clouds" finds our man Keanu as a soldier who returns from World War II and is promptly dumped by his wife. Heading north to Sacramento, he encounters a pregnant woman who’s been ditched by her boyfriend and is travelling home to her family’s vineyard. He agrees to pose as her husband. Inevitably, and in the best way possible, they fall in love.
19 / The Gift
Before this project from "Spider-Man" director Sam Raimi, most wouldn’t have envisioned Keanu Reeves as a terrifying redneck who abuses his wife and is pretty much pure evil. So, it’s a surprise that the part of Donnie Barksdale fits the actor like a glove. It's also nice to report that this entire movie is an underrated film noir gem.
20 / Street Kings
While critics and audiences were lukewarm on this tale of corruption, redemption, and somewhat dubious street cops, it’s a hard-boiled, effective crime thriller from "Training Day" writer David Ayer, and features one of Keanu’s toughest performances. He’s 100% believable as a thuggish police detective who may or may not have true justice in mind. He’s matched by future Captain America Chris Evans as his younger, more discerning partner.
Chuck is an editor/writer who's worked for NCM, Fandango, Movies.com, MediaTrip, Hollywood.com and Newsweek. His favorite movie is "Jaws." He's definitely a dog guy.