We Ranked Keanu Reeves's Most Memorable Romantic Lead Roles by Keanu-ness
2019 was the year of the Keanussance and, as such, we Keanu Stans took it upon ourselves to watch as many of his romantic films as possible. (It was hard, thankless labor, which we undertook for purely selfless reasons.).
Why do we love Keanu? Perhaps because it's so refreshing to find a handsome man who has been in the game for as long as he has and still maintained his reputation of being a straight-up Good Guy. There are no #MeToo scandals, no past racist tweets — just an earnest actor living his life and doing good deeds for his fans. It’s breathtaking.
He’s also a weirdo, and internet culture loves a weirdo.
VIDEO: Keanu Reeves Hand & Footprint Ceremony
Thus, we’ve taken it upon ourselves to rank seven of his most-memorable romantic films on an arbitrary point scale based on what we’re calling Keanu-ness — that intangible, elusive quality that makes Keanu, Keanu. We hope you enjoy it as much as you enjoy these most Keanu cinematic treasures.
Sweet November (2001)
Character: Nelson Moss
Love interest: Charlize Theron as “free-spirited dog walker” Sara Deever
Keanu-ness Score: 1/10
Facial hair status: American Psycho-level smoothness
Watch for: Keanu poorly serenading Charlize Theron in a full tuxedo.
This is the kind of movie you could only find in the year 2001. Keanu stars as Nelson Moss, a workaholic ad exec (Ben Barry vibes?) who meets quirky pet lady (Polly Prince vibes?) on the verge of a nervous breakdown (literally every rom-com in the early-aughts vibes?).
The premise is stranger than the melodramatic, romance-novel-esque movie poster would lead you to believe: Free spirit Sara takes messed-up men into her unrealistically large San Francisco apartment for a month at a time to help them learn how to enjoy their lives, and Keanu’s Nelson just happens to be her ideal candidate for the month of November after he’s fired from his high-powered job, and his girlfriend Angelica (an underused Lauren Graham) breaks up with him.
Charlize’s Sara really exudes the most Keanu energy here with her unconventional “freak” antics, as she teaches Nelson to live in the moment and also to know the gift of dogs. (There are so many dogs.)
In the landscape of Keanu’s films, Nelson is perhaps one of the most un-Keanu-like characters — basically, he’s an asshole with no morals. Despite an incredible character arc that finishes with Mr. Reeves delivering a log of salami to his beloved (a Very Keanu move), we hate to see our man so literally buttoned up, even if for just the first third of the film. — Sam Reed
Destination Wedding (2018)
Love interest: Winona Ryder as Lindsay, the anxious wedding guest watching her ex tie the knot
Keanu-ness Score: 3/10
Facial hair status: Fully bearded
Watch for: Reeves and Ryder's chemistry.
It seems impossible to round up Keanu Reeves and Winona Ryder, icons of the '90s and the present day, and make a boring movie. Destination Wedding, however, achieves the impossible. As the cynical Frank, Reeves’s Keanu-ness is toned down in favor of biting negativity, but being that he is Keanu Reeves, his charm still shines through. What makes up for the movie, though, is that its press tour gave us the gift of finding out that Keanu Reeves and Winona Ryder might technically be married to each other. — Kimberly Truong
The Lake House (2006)
Character: Alex Wyler
Love interest: Sandra Bullock as the over-worked and under-apprecated Dr. Kate Forrester
Keanu-ness Score: 5/10
Facial hair status: L.L. Bean model but make it romance
Watch for: Keanu’s most-excellent turtleneck sweaters.
Basically a cross between the Sisterhood of the Traveling Pants (but swap pants for glass houses and sisters for romantic partners) and any movie about time travel, The Lake House is peak fantasy romance. There isn't much room for Keanu’s eccentric nature to shine through, but damn if he doesn’t look good in a thick turtleneck sweater. His vulnerability — another key Keanu trait — is what really stands out and makes him believable as the romantic lead in a long distance (in years, that is) relationship with Sandra Bullock’s lonely Kate and her questionable 2006 haircut. (Sorry, Sandra.) — S.R.
The Private Lives of Pippa Lee (2009)
Character: Chris Nadeau
Love interest: Robin Wright as Pippa Lee, a housewife with a dark past on the edge of a nervous breakdown
Keanu-ness Score: 8/10
Facial hair status: Clean shaven but in a ‘90s alt rock lead singer way
Watch for: Keanu’s collar bone-to-pelvis chest tattoo of Jesus.
The only thing that makes up for the lack of Keanu screen-time is the stacked cast. And just when you thought nothing could be more sensational than Julianne Moore playing the exploitative artist girlfriend of young Pippa’s (Blake Livley's) closeted Aunt (Robin Weigert), you find out that the whole project was produced by Brad Pitt.
Though this film is primarily about the evolution of the titular Pippa Lee (or her “private lives,” if you will), don’t worry — there’s plenty of Big Keanu Energy to go around when the actor does turn up onscreen.
Keanu plays Chris, the “half-baked” divorced son of Pippa’s neighbors in the retirement community she moved to after her esteemed publisher husband’s third heart attack. As their vast age difference begins to wear on her marriage, Chris emerges as the eccentric, failed clergyman-turned-staunch atheist foil to everyone in her tightly controlled life. Nothing illustrates this “savior” complex more than the scene in which Pippa stumbles across Chris in a random street, bending over a random dog who had just been hit by a car. When the camera pans across the deeply empathetic Chris, stroking the dying pup’s head as the music swells — I really felt that. — S.R.
Something’s Gotta Give (2003)
Character: Julian Mercer
Love interest: Diane Keaton as Erica Barry, a romantically frustrated playwright
Keanu-ness Score: 9/10
Facial hair status: Gone, but not forgotten
Watch for: Keanu Reeves telling Diane Keaton that she's "incredibly sexy."
We’ll come right out and say it: Something’s Gotta Give could not be made in the year 2019, because people (myself included) would riot over Diane Keaton’s character choosing Jack Nicholson's character — a man she meets because he is initially dating her young daughter — over Keanu Reeves's. Not only does he look like Keanu Reeves, Julian is a doctor who respects her ambitions as a playwright, and who does things like kiss her on the neck at dinner and say, “I knew you’d smell good.”
Not to mention, after her brief, torrid affair with Jack Nicholson’s character (during which she ghosts Julian), Erica is reunited with Julian when her sister spots him at a farmer’s market, of all places. He then comes to her house with a bouquet of hand-picked (presumably locally grown) flowers, joking, “These are for you to give me when you apologize.” We love an eco-friendly, forgiving man! — K.T.
A Walk in the Clouds (1995)
Character: Paul Sutton
Love interest: Aitana Sánchez-Gijón as Victoria Aragon, the traveler returning home to her family vineyard
Keanu-ness Score: 10/10
Facial hair status: Non-existent
Watch for: Keanu Reeves in a white tank, dancing with fake wings.
Perhaps the most sweeping romance of Keanu’s onscreen romances, A Walk in the Clouds is also peak Keanu. His character spends the movie defending a woman from a creep on the bus, falling in love with said woman, dancing with her among a line of fiery torches, and, at one point, taking off his flannel shirt to try to tame the flames that have engulfed her family’s vineyards. — K.T.
Always Be My Maybe (2019)
Character: Keanu Reeves
Love interest: Ali Wong as Sasha Tran, a successful, ambitious chef
Keanu-ness Score: 20/10
Facial hair status: Perfectly stubbled
Watch for: Keanu's entrance, soundtracked by AWOLNATION's "Sail."
As the movie that kickstarted the Keanussance of 2019, it makes sense that Netflix’s rom-com of the summer features Reeves’s essence dialed up all the way to the max. Even playing an exaggerated, over-the-top version of himself, it’s easy to see why he so easily romances Ali Wong’s Sasha and why he poses as a threat to her childhood sweetheart, Marcus (Randall Park).
Wong has spoken about her motives for casting Reeves (aside from just wanting to be able to kiss him), telling Vulture, “It’s always been important to me, to express my desire and attraction toward Asian-American men. Since I first watched Speed, I was very aware that Keanu was Asian-American because my family and community wouldn’t shut up about it. Maybe other people didn’t know, but I never forgot that.”
And, well, no one could deliver the line “The only stars that matter are the ones you look at when you dream” the way Keanu Reeves could. — K.T.