The Top 5 Cary Elwes Movies

Actor Cary Elwes has had a strange career. Pegged as a leading man coming off of his breakthrough performance in The Princess Bride, Elwes never popped as a leading man after that film went down in history as one of the most delightful family movies of all time. After that came many high profile roles in big movies but Elwes receded into character actor roles rather quickly for a man of his leading man good looks and proper English diction.

Was Cary Elwes ever interested in being a huge movie star? His career would suggest no, that perhaps he simply preferred not being at the front of a movie. Perhaps playing villains or secondary leads was more his style. Whatever the reason was that kept Cary Elwes from the leading man adulation so many predicted for him, it never stopped him from making a big impression even in lesser movies.

With that, and Cary Elwes’ latest supporting role, in the horror movie, The Unholy, arriving in theaters on April 2nd, here’s a look at the 5 Best Movies in the long, 40 plus year career of Cary Elwes.

5. Hot Shots - 1991 - If there is one trait we can definitely assign to Cary Elwes without having met him, it’s self effacement. Elwes doesn’t take himself too seriously. He has a willingness to be the butt of a joke regardless of the joke. He showed that a little in The Princess Bride but it became a defining trait in 1991 when Elwes played Val Kilmer to Charlie Sheen’s Tom Cruise in a send up of Top Gun in Hot Shots. Elwes’ ability to be pompous and egotistical and get deflated are the perfect foil for Sheen but it’s the goofiness that Elwes throws himself into with aplomb that earns the biggest laughs.

4. Robin Hood Men in Tights - 1993 - Admittedly, Robin Hood Men in Tights has not aged well in many, many ways. That said, there is no denying that Cary Elwes is brilliantly funny in the role of the comic Robin Hood. He’s a regular Bugs Bunny crossed with Errol Flynn but with a humor that entirely belongs to Elwes in the way he always throws himself into the goofiest of jokes. Elwes channels Errol Flynn thoroughly, especially his remarkable ability to smile during swordfights.

3. The Cat’s Meow - 2001 - Mostly forgotten today, The Cat’s Meow is a terrific movie that features Elwes in his favored supporting role as a legend who never was. Thomas Ince was a very successful Hollywood director in the early, early days of film until one night he attended a party on a yacht owned by William Randolph Hearst and Hearst's wife, actress Marion Davies, played by Kirsten Dunst. Ince and Davies had become friends and worked together and he was so much a confidante that she confessed to him an affair she’d once had with Charlie Chaplin, played here by Eddie Izzard. This confession may or may not have directly led to Ince’s murder by Hearst, played by the great Edward Hermann. In a cast of absolute scene stealers that also includes Jennifer Tilly and Joanna Lumley, Elwes is a stand out as the doomed director whose life ended and his legacy wiped away by the powerful man who many believe murdered him.

2. Saw - 2004 - Cary Elwes never really went away, he took smaller roles and supporting roles, even a TV movie, but he was always around. And yet, when he starred in Saw in 2004 it was shocking to see the debonair and dashing former Dread Pirate Roberts, doughy and disheveled and leading a shock horror movie. It’s brilliantly subversive casting. Elwes is not the first name that would come to mind for this material and that’s exactly what made him so perfect for it. When the climax arrives and he makes his climactic and shocking choice at the end of the movie the extra shock of seeing a deeply committed Elwes committing a horror upon himself raises the stakes on what could have been just another slasher movie.

1. The Princess Bride - 1987- Was there ever a doubt? Could you even imagine Cary Elwes making a better movie than The Princess Bride? That’s probably why Elwes receded into character roles and villains, the shadow of Wesley and Buttercup has always been inescapable. Elwes created a beloved character that would forever haunt his career and while he appears perfectly at peace with that fact, it’s still strange to think that the greatest, definitive success of someone’s career could also derail and detract from that career. Detract from our perspective, certainly not from his. Elwes, to my knowledge, has never shared any regrets over the way The Princess Bride defined him and his career.