The biggest challenge faced by the casting team behind the James Bond franchise is finding the perfect actor to play Bond himself when the series is rebooted every few years. But on top of choosing the perfect actors to play 007, the casting agents have to find ideal candidates for the roles of Bond girls, megalomaniacal villains, and incarnations of beloved supporting characters like M and Q.

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The casting team doesn’t always hit the mark — Denise Richards in The World is Not Enough stands out as a glaring example of miscasting — but the majority of roles have been perfectly cast.

Perfectly Cast: Sean Connery As James Bond

Sean Connery as James Bond lighting a cigarette in Dr. No.

Sean Connery sadly passed away earlier in 2020, but at least the legendary actor got to live a full, rich life beforehand. Ever since he played the first big-screen incarnation of 007, Connery has been one of the most revered and recognizable movie stars in the world.

With his ice-cool charisma and gentlemanly edge, Connery was the perfect actor to bring Bond to life. His performance defined the character for generations to come.

Almost Cast: Cary Grant

Cary Grant running from crop duster in North by Northwest

When the producers behind Dr. No first set out to bring James Bond to the big screen in the hopes of launching a lucrative spy movie franchise, their top choice for the role was North by Northwest star Cary Grant.

However, Grant wasn’t cast for a number of reasons: he didn’t want to commit to three movies (as was stipulated by his potential Dr. No contract), the producers eventually thought he might be too old, and the salary that the actor could command was equal to the movie’s entire budget.

Perfectly Cast: Gert Fröbe As Auric Goldfinger

Gert Frobe as Goldfinger

Sean Connery’s initial run of Bond movies took three entries to establish the franchise’s now-familiar formula. The one that really clinched it was Goldfinger, his third outing in the role. This is the movie that introduced Bond girls, opening set pieces, and theme songs by contemporary pop artists.

It also introduced the notion of megalomaniacal villains with the title character, Auric Goldfinger. Gert Fröbe’s performance as Goldfinger set the stage for every Bond villain that followed.

Almost Cast: Orson Welles

Orson Welles standing on newspapers in a still from Citizen Kane

The Bond producers’ first choice for the role of the titular villain in Goldfinger was Orson Welles, but as one of the most sought-after artists in the world, he was alas too costly.

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Welles would go on to play a different Bond villain, Le Chiffre, in the 1967 version of Casino Royale, a non-Eon production that lampoons the 007 mythos.

Perfectly Cast: Eva Green As Vesper Lynd

Eva Green as Vesper Lynd sitting on a train in Casino Royale

Vesper Lynd in Casino Royale is one of the best Bond girls in the franchise’s history because she doesn’t conform to any of the usual stereotypes. She’s never unnecessarily sexualized (partly due to a suggestion by Daniel Craig) and she’s just as competent at her job as Bond is.

Eva Green was a brilliant match for Daniel Craig, bringing tangible tension to their characters’ flirtatious back-and-forth, and her dramatic scenes have real nuance rarely found in the Bond franchise.

Almost Cast: Audrey Tautou

Audrey Tautou in Amelie

Before Eva Green was cast to play Vesper Lynd in Casino Royale, Audrey Tautou was being seriously considered. However, she turned it down because of scheduling clashes with the filming of The Da Vinci Code.

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Prior to Green’s casting, the producers considered a laundry list of A-list stars: Jennifer Connelly, Scarlett Johansson, Angelina Jolie, Keira Knightley, Rachel McAdams, Thandie Newton, Michelle Pfeiffer, Charlize Theron, Naomi Watts, and Olivia Wilde.

Perfectly Cast: Richard Kiel As Jaws

Richard Kiel as Jaws biting a cable in James Bond

It’s not easy to make a henchman memorable because they’re expendable by their very nature, but it didn’t take long for Jaws to catch on as a fan-favorite Bond character.

He was only supposed to appear in one movie, but Richard Kiel’s performance was so beloved by the fanbase that he was not only kept around for future sequels; he was given bigger and bigger roles to accommodate the demand.

Almost Cast: David Prowse

David Prowse in A Clockwork Orange

When the Bond producers were looking for a physically intimidating actor to portray Jaws, they considered David Prowse, who recently passed away and made his name as the physical presence of Darth Vader in the original Star Wars trilogy.

Ironically, Jaws played a major role in Moonraker, which sent James Bond to space to cash in on the space movie trend that followed the success of Star Wars.

Perfectly Cast: Daniel Craig As James Bond

Daniel Craig as James Bond, in tuxedo and sitting at table

The 007 producers faced a difficult challenge when they started looking for a new actor to play James Bond in their gritty Casino Royale reboot because they needed a performer with all the suaveness of a traditional Bond, but with a dark edge not seen in the pre-Bourne Bond movies.

Although there was initially some controversy due to his naturally blond hair, Daniel Craig wound up being the perfect choice for this movie.

Almost Cast: Henry Cavill

Henry Cavill as Superman

When the Bond producers were recasting the role of 007 for Casino Royale, the shortlist came down to Daniel Craig and Henry Cavill. The role ultimately went to Craig, because Cavill was in his early twenties and the producers deemed him too young for the part, even though Casino Royale is an origin story following a young 007.

This worked out for Cavill in the end, of course, as he was eventually cast to play Superman in the DC Extended Universe (although his contract is currently up in the air as his management team negotiates with Warner Bros. execs).

NEXT: The Lord Of The Rings: 5 Roles That Were Perfectly Cast (And 5 Actors Who Almost Played Them)