Cary Elwes The Princess Bride (1987)

Cary Elwes was twenty-four when The Princess Bride shot. He had been raised in London — son of the painter Dominic Elwes — trained at Sandhurst Theatre and the Actors Studio in New York, and arrived in Hollywood with a handful of credits including Another Country (1984), Oxford Blues (1984), and Lady Jane (1986). Rob Reiner saw him in Lady Jane and offered him Westley sight unseen.

"He had to be young, romantic and athletic. And he had to be funny. Cary was the only actor who had all those qualities." — Rob Reiner, Vanity Fair (2012)

Westley as three roles inside one body

The character is constructed in three layers: the farm boy (a gentle, formal voice; the "as you wish" refrain), the Dread Pirate Roberts (the controlled, almost amused voice of a one-man pirate identity who has been waiting years to do exactly this rescue), and the post-Pit-of-Despair Westley (a man whose body has been killed once and brought back, who can barely lift his arms, who runs the team from a wheelbarrow). Elwes plays all three convincingly inside the same film, and the third — the bedroom scene with Buttercup, the bluffed sword duel with Humperdinck — is the most underrated work in the picture.^b38

The fight training was real

Elwes and Mandy Patinkin trained for months with Bob Anderson and Peter Diamond — two of the most prolific film fight coordinators of the era. They learned the entire duel ambidextrously so the left-handed reveal could play in long takes without doubles.

"We trained five days a week, two-three hours a day, for months. We did most of it ourselves. The whole point was to be able to shoot it in long takes without cuts." — Cary Elwes, As You Wish: Inconceivable Tales from the Making of The Princess Bride (2014) (book, not available online)

Elwes broke his big toe early in the shoot when André the Giant — bored on set — let him drive his ATV. The injury was hidden in the boot Westley wears in the Pit of Despair scenes; Elwes hobbled through the second half of the shoot. (vanity fair excerpt)

Career before and after

Before Westley, Elwes had played romantic and military roles in British and American period films. After, he traded on the Princess Bride recognition for a long working career — Glory (1989), Days of Thunder (1990), Bram Stoker's Dracula (1992) where he played Lord Holmwood, The Crush (1993), Mel Brooks's Robin Hood: Men in Tights (1993) which deliberately echoed his Westley persona, Twister (1996), James Wan's Saw (2004), and a long stretch of television including The X-Files and Stranger Things (where in season 3 he played the villainous mayor Larry Kline).

He has spoken at length about The Princess Bride across decades — most extensively in the 2014 memoir As You Wish, which was published for the film's twenty-fifth anniversary and stayed on the New York Times bestseller list for five weeks. His position has been steady: the film was the best experience of his professional life, and he expected the world to know about it.

"It was the most magical experience that I've ever had on a film. There was a sense from all of us that something special was happening, even though we had no idea anyone would ever care." — Cary Elwes, The Hollywood Reporter (2014)