THE BEST: 1. Speed (1994)
Pop quiz, hot shot: Name a ’90s movie with a preposterous high-concept premise, an unhinged psycho villain chewing the scenery like a wad of Bazooka, a relatively unknown ingenue who would parlay her flip performance into becoming the next Julia Roberts, and a buzz-cut hero of few words who refused to give up, give in, or play by the rules. If you came up with Jan de Bont’s perfectly engineered Die Hard-on-a-bus thriller Speed, congratulations! Reeves made a handful of better movies than this one, but none more deliciously silly and white-knuckle tense.
2. The Matrix (1999)
Always choose the red pill, folks. Welcome to the movie that took Philip K. Dick future-shock sci-fi and elevated it to a PhD meditation of what-is-reality mental gymnastics, fueled by the sort of then-revolutionary eye candy (bullet time!, blur-fast chop-socky workouts) that comes along once a decade if we’re lucky. The Wachowskis’ through-the-looking glass meta-thriller hasn’t aged as well as some who predicted it would inaugurate a new cinematic form might have expected. But it’s still the smartest, most exhilarating movie on Keanu’s resume. Enter the sequels at your own risk.
3. John Wick (2014)
This film is bone-crunching proof that you should never count out a movie star who seems past his box office sell-by date. John Wick, and the alternate universe of assassin cabals it fleshed out with giddy ingenuity, was the movie no one saw coming and didn’t know we needed until it arrived in all of its adrenalized glory. The plot is ridiculous, by-the-numbers revenge flick pulp (they killed his dog — big mistake!), but Reeves’ stoic, Easter Island-statue screen presence works like violent, whiplash gangbusters. Plus, you get Ian McShane at his Ian McShane-iest!
4. Point Break (1991)
Has there ever been a better character name than Johnny Utah? Before Kathryn Bigelow had Oscar statuettes in her eye line, she cemented her muscular action-flick bona fides with this guilty-pleasure heist flick starring Reeves as an undercover cop embedding with a gang of beach-bum adrenaline-junkie crooks led by Patrick Swayze’s Zen surfer bro Bodhi. Reeves is essentially the straight man here, but he turns this hunk of early ‘90s cheese into gourmet fromage.
5. John Wick: Chapter 2 (2017)
The brooding badass is back and this time it’s not his dog he’s avenging, but his muscle car — or something. John Wick 2 doesn’t so much up the stakes of the first film as double down on its secret world of gentleman hitmen, fleshing out the franchise’s rich cinematic universe of hitman hotels and Masonic rules and regulations. The action is first rate, too. This sequel could have been just another cash-in to a surprise hit, but instead it aims higher and gets pulpier.
6. Bill & Ted’s Excellent Adventure (1989)
It would take years for Keanu to bust out of the deliriously sunny airhead pigeonhole that this comedy put him in. But it’s hard to imagine a comfier, more bespoke gilded cage. Reeves and costar Alex Winter (a.k.a. The Wild Stallyns) are high school dim bulbs who turn out to be a lot more profound than they first seem. Disciples of the Jeff Spicoli school of dazed-and-confused slackers, Bill and Ted step inside a time-travel phone booth and swap stoner banter with everyone from Socrates to Billy the Kid to Napoleon in their quest to pass history class. It’s a toke of pure daffy joy.
7. River’s Edge (1986)
From early on, Reeves gave off the vibe of someone who was — oh, let’s just come out and say it — not all that smart. But when it came to charting his career, the actor was remarkably canny. Most 22-year-olds with Reeves’ shambling, mannered charisma and So-Cal good looks would have turned up their noses at a bleakly nihilistic indie like Tim Hunter’s disaffected youth masterpiece (at a time when indies weren’t quite cool yet). But not Reeves. He already had the inner compass to zig when others might zag. This is a haunting and uncompromising film, and Reeves is hypnotically naturalistic in it.
8. Parenthood (1989)
Ron Howard’s ensemble comedy about family and its discontents is surprisingly poignant underneath its screwball veneer. There are a lot of great performances in this movie (Dianne Weist, Steve Martin, Tom Hulce), so it’s easy for any cast member to get lost in the eventful mix. But Reeves, as Martha Plimpton’s hilariously histrionic boyfriend, turns absurd grand romantic gestures into tiny, recognizable, heartfelt moments of what it’s like to be young, foolish, and madly in love.
9. Freaked (1993)
Directed by Reeves’ Bill & Ted costar, Alex Winter, this low-aiming, off-the-wall comedy never quite achieved the midnight-movie cult status it so richly deserved. Reeves, who’s virtually unrecognizable as low-rent freak show attraction Ortiz the Dog Boy, isn’t the star here (how could he be when you’ve got Mr. T as an emo bearded lady and Randy Quaid as a demented carny barker?), but his throwaway presence proves the level of minute detail Winter was obsessively after. Truly, one of the most bizarre underseen curios of the ‘90s.
10. My Own Private Idaho (1991)
Director Gus Van Sant mixed Shakespeare with Midnight Cowboy in this art house mash-up about down-and-out street kids scratching to get by. The chemistry between Reeves (in the well-to-do wastrel Prince Hal role) and River Phoenix (as a narcoleptic gay hustler) is so electric it virtually shoots off sparks. In a better world — a world where Phoenix didn’t leave us at 23 — this would have been one in just a string of movies featuring these two Gen-X giants.
11. Bram Stoker’s Dracula (1992)
Francis Coppola’s lavish, old-school take on the vampire mythology is pretty much the definition of a love-it-or-hate-it proposition. When it first came out, I hated it. Over time, I’ve come around. Not necessarily because of Reeves’ performance as Jonathan Harker, but this is definitely a movie worthy of reappraisal. What at first seems like a stilted, wrong-century, cast-for-his-looks performance actually turns out to be pretty…interesting. The movie casts a spell and Reeves only adds to it with his mannered, all-in acting.
12. The Devil’s Advocate (1997)
Here’s a movie that should be on the must-see list for devotees of over-the-top Al Pacino performances and Angel Heart-style guilty pleasures alike. How over the top is Pacino? Well, he plays Lucifer, so you can pretty much do the math. But Reeves keeps things tethered to the here and now, essentially playing a variation on Tom Cruise in The Firm, albeit with his lawyerly soul literally on the line. This is daft, overblown, silly stuff to be sure, but it’s also a hell of a lot of fun. Bonus: There’s a nice pre-fame performance from Charlize Theron as Reeve’s sacrificial wife.
13. A Scanner Darkly (2006)
Another case of Reeves zigging when his more career-minded peers might have zagged. Coming off the big-budget box office flameout Constantine (underrated? discuss.), the actor went back to the experimental indie track that was never too far from his heart for this roto-scoped Richard Linklater gem. Reeves has always been most interesting when he takes a sharp left onto the road less traveled, and A Scanner Darkly is just another example of why that is.
14. Dangerous Liaisons (1988)
Granted, Keanu is at best the fourth most interesting thing in Stephen Frears’ scheming erotic roundelay (and how he could he not be, fighting to keep up with John Malkovich, Glenn Close, and Michelle Pfeiffer?). But dupes and cuckolds need a sympathetic shout-out from time to time, too. I haven’t seen this one since Cruel Intentions reverse-engineered it for the MTV generation, but I’m guessing all of the amoral scheming and heaving-corset seduction still holds up nicely.
15. Much Ado About Nothing (1993)
As the villainous Don John, Reeves isn’t the main attraction here (although his brooding good looks rival the Tuscan-sun scenery). Still, there’s something to be said for a young Hollywood movie star subsuming his ego to be in an ensemble with his betters (Denzel Washington, Emma Thompson, Kenneth Branagh) and tackle Shakespeare. Reeves has never seemed particularly interested in being a bankable, klieg-light movie star as much as a stealth-weapon actor stepping outside of his comfort zone to try something new. He’s the anti-Tom Cruise. I can’t say that I honestly love this movie, but I love that Reeves signed on for it and didn’t embarrass himself in the process.
THE WORST: 1. Even Cowgirls Get the Blues (1993)
Loyalty is an underrated virtue, and an exceedingly rare one in Hollywood, so you have to respect Reeves’ devotion to his My Own Private Idaho director Gus Van Sant in signing on for this adaptation of Tom Robbins’ cult novel. But holy s—, is this a terrible movie! Reeves rightly emerged unscathed from this dopey misfire and, luckily, star Uma Thurman had Pulp Fiction on deck to power wash the stink of this one from her resume
2. Johnny Mnemonic (1995)
This confounding William Gibson cyberpunk thriller has its fans. And guess what, they’re all nuts. I know, you’re wondering how a movie that features the crazy quilt cast of Dolph Lundgren, Udo Kier, and Ice-T could be all bad. Well, I don’t know what to tell you other than it…just…is.
3. The Matrix Revolutions (2003)
The third and worst of The Matrix trilogy, this is what happens when filmmakers believe they can do no wrong and get high on their own supply. A folly that feels like a thickety academic treatise, The Matrix Revolutions makes you wish you could go back, choose the blue pill, and wake up in your bed believing the whole thing never happened.
4. The Day the Earth Stood Still (2008)
Klaatu barada nikt — oh no!
5. The Lake House (2006)
Anyone who loved Keanu and Sandra Bullock together in Speed had their hearts broken when he decided to sit out the sequel, Speed 2: Cruise Control. Their hearts were crushed to dust a second time when the two stars were finally reunited in this schmaltzy dud where they’re virtually kept apart the entire movie like some sort of cruel joke.