Though it's not particularly easy viewing, Tim Hunter's dark and gritty River's Edge (1986) features an early breakout performance for Reeves, who plays a teenager covering up a murder for a friend. Based on a real-life case, River's Edge — also starring the late Dennis Hopper — paints a portrait of adolescence so bleak it's been called "the darkest teen film of all time." And though Reeves is known for playing likable characters, he showed here at a young age that he has a gift for quiet discomfort that can be haunting.

A period drama based on the 1782 French novel Les Liaisons Dangereuses, Stephen Frears' Dangerous Liaisons (1988) boasts an all-star cast including Michelle Pfeiffer, Glenn Close, John Malkovich, Uma Thurman, and a young Reeves playing a music teacher caught up in the elite's political games. The film won Best Costume Design, Best Production Design, and Best Adapted Screenplay at the 61st Academy Awards.

Reeves plays a genial California stoner who gets the chance to meet historical greats like Napoleon and Socrates in the time traveling romp Bill & Ted's Excellent Adventure (1989), directed by Stephen Herek. The film spawned two sequels — Bill & Ted's Bogus Journey (1991) and Bill & Ted Face the Music (2020) — and gave Reeves his first iconic role. In a word: "Excellent!"

Another early lovable doofus role for Reeves, the actor had a small, but memorable part in Ron Howard's Parenthood (1989). As Julie's (Martha Plimpton) boyfriend, Reeves brings comedic relief to the drama and defends a young Joaquin Phoenix after he's caught masturbating, exclaiming, "That's what little dudes do." With a stacked cast including Steve Martin and Dianne Wiest, Parenthood was ultimately adapted into a TV series — twice.

In Academy Award-winning director Kathryn Bigelow's Point Break (1991), Reeves plays Johnny Utah, a FBI agent who goes undercover to catch a band of surfing bank-robbers led by Bodhi (Patrick Swayze). One of his first big leading roles, Reeves' vulnerable portrayal adds heart to what could have been a typical action film. The actor has since said that it's one of the movies fans talk to him about the most.

Widely regarded as a landmark film in the LGBTQ+ community, My Own Private Idaho starred Reeves as Scott Favor, a sex worker and friend of River Phoenix's Mikey Waters, who confesses his love for Scott but is, ultimately, rejected. Directed by independent filmmaker Gus Van Sant and based on Henry IV, the film allowed Reeves to play a complex and aloof foil to Phoenix's vulnerable Waters.

In Kenneth Branagh's gleeful, over-the-top adaptation of the Shakespeare play of the same name, Reeves stars as Don John, the evil half-brother of Denzel Washington's Don Pedro, alongside a cast including Emma Thompson, Michael Keaton, and Kate Beckinsale. Though at the time he had been known for goofy roles like Ted, in Much Ado About Nothing (1993), Reeves proved he could pull off a reserved, evil role (and a villainous beard).

Building on Point Break's momentum, Jan de Bont's Speed (1994) cast Reeves as a leading man once again. This time, instead of infiltrating a gang of surfers, he has to stop a terrorist played by Dennis Hopper while on a bus driven by Sandra Bullock, which, if it goes under 50 miles per hour, will explode. This wild concept leads to an exhilarating, gripping film that solidified Reeves' place as one of the action hero greats.

Science fiction film The Matrix (1999), directed by Lana and Lilly Wachowski, quickly became one of the most influential films of the 1990s, winning Academy Awards for Best Film Editing, Best Sound, and Best Effects for both Sound and Visual Editing. As Neo, a computer hacker with some softer vulnerability, Reeves also redefined the action hero by playing against the testosterone-fueled mega-buff GI Joe type. Alongside Laurence Fishburne and Carrie-Anne Moss, Reeves pulled off action sequences that remain iconic today, as evidenced by the remaining popularity of trench coats and sunnies on Halloween.

Reeves showed off his romantic side in the Nancy Meyers comedy Something's Gotta Give (2003), in which he played Diane Keaton's love interest. With an adorable age gap and palpable chemistry, Reeves and Keaton are part of what make Something's Gotta Give stand out even among other Meyers classics.

Using the animated technique of rotoscoping, in which actors are filmed and then traced over by animators, Richard Linklater's science fiction film A Scanner Darkly (2006) tells the story of a paranoid, drug-addicted, police-surveillance state. Alongside a star-studded cast including Robert Downey Jr., Woody Harrelson, and Winona Ryder, Reeves plays a narcotics officer who himself becomes hooked on a hallucinogenic drug while undercover.

Back in the spotlight as a leading man, Reeves made a professional comeback with John Wick (2014), the Chad Stahelski-led action thriller following a former assassin tracking down the men who wronged him and killed his beloved puppy, a gift from his late wife. In the film that kicked off a wildly successful franchise that continues to this day, Reeves creates a distinct protagonist, one you want to root for despite his penchant for, well, assassinating people. With a seemingly unassuming name, John Wick is the sleeper hit that nobody saw coming.