The Canadian actor first teamed up with Ryder for 1992’s Bram Stoker’s Dracula and the duo later reunited for 2006’s A Scanner Darkly. More than a decade later, the pair took on roles in 2018’s Destination Wedding, a quirky romantic comedy that sees their characters move from enemies to lovers as they connect over their shared hatred of weddings.
“I wish I could do every movie with him,” the Stranger Things actress told Entertainment Weekly in August 2018. “The biggest thing for me was the opportunity to get to work with Keanu again. It was a very surprising script in that it doesn’t really have the tropes that a lot of romantic comedies do. … It’s refreshing and sort of a challenge. It was a special time. Any time with Keanu is a special time for me.”
Reeves, for his part, couldn’t imagine making the film without Ryder by his side. “Having known each other for so long, with that is also the rapport, the trust. We have a mutual outlook on the world. In terms of working together, we’re cut from the same cloth,” he told the outlet. “There is that trust; there is that facility. … We know each other, we love each other, we’re fans of each other’s.”
Fans of romantic comedies know Reeves has a knack for playing up his more charismatic side, as portrayed in 2003’s Something’s Gotta Give. Though his character may not have ended up with Keaton’s in the Nancy Meyers classic, the former costars reminded viewers of their undeniable chemistry while reuniting at the 2020 Oscars.
“It’s been a long time since you and I made that movie. Remember Something’s Gotta Give?” Keaton teased before the pair announced the winner for Best Original Screenplay. “That was a lot of crying in there, Keanu, lots of laughing and crying. And well, we had some really, well let’s be frank, good times.”
While Reeves teased that the best times on that movie’s set were between Keaton and Jack Nicholson — whose character famously gets the girl — Meyers was as pleased by the reunion as her biggest fans.
“Whoa,” she teased via Instagram at the time. “Maybe they did end up together.”
Scroll down to relive more of Reeves’ best onscreen romances!