Esteemed veteran actor Sean Connery recently passed away, but he left a wealth of amazing roles behind for fans to celebrate and share with entire new generations of film lovers. He made a name for himself as the original suave secret agent James Bond in the film adaptations of Ian Fleming's classic novels before branching off into a diverse array of roles both small and epic.
Connery's wide body of work was anything but stereotypical or typecast. He's portrayed some of the coolest characters in movie history—not to mention some of the wackiest. Here are five of Sean Connery's most killer roles, and five in which he went off the deep end in the most enjoyable ways imaginable.
Wackiest: Allan Quartermain (The League Of Extraordinary Gentlemen)
Aptly nicknamed "X-Men for Librarians," The League Of Extraordinary Gentlemen would prove to be Connery's final film role before he quietly exited the business and maintained a low profile. Despite his advanced age of 73 years, Connery was gung-ho for an action/adventure epic in the same vein as previous roles in films like Highlander.
Connery's witty one-liners and largely believable action movie presence was a testament to his unprecedented level of energy, but a poor script and lackluster audience reception meant that League would make back a large portion of its budget without sailing on to stardom.
Coolest: Daniel Dravot (The Man Who Would Be King)
Kudos to the man who thought of putting the illustrious Michael Caine and Sean Connery in the same movie together, because it worked like an absolute charm. The Man Who Would Be King is one of the most underrated adventure epics of all time, and one that every moviegoer owes it to themselves to see.
Connery plays Daniel Dravot, a man who finds himself crowned king after an isolated people believe him to be a God incarnate. Connery plays the role masterfully alongside Caine in this adventure romp loaded with action, a healthy dose of comedy, and a twisted ending.
Wackiest: Sir August de Wynter (The Avengers)
Connery gave up all semblance of self-respect when he joined the cast of 1998's The Avengers alongside Ralph Fiennes and Uma Thurman. As the main antagonist Sir August de Wynter, he got an opportunity to play up some of his Scottish heritage while portraying a villain, which was rare for him.
Unfortunately, The Avengers was nuts beyond all hope of relief, and Connery got lost in the madness of it all. Still, watching him overact as a megalomaniacal eco-terrorist is quite a fun experience, proving once and for all that he was fully capable of making a terrible movie a little bit better.
Coolest: Marko Ramius (The Hunt For Red October)
It could be argued that Sean Connery's acting career was rejuvenated with his amazing performance in the film adaptation of The Hunt For Red October. Connery played Marko Ramius, a Russian naval captain in charge of a super-advanced submarine undetectable by radar.
His steeled portrayal of the bold, courageous, and sympathetic captain won him accolades and made him the main star in a movie that was supposed to focus primarily on the character of Jack Ryan. In the end, none of that mattered. The movie was excellent, as was his performance.
Wackiest: Professor Henry Jones (Indiana Jones & The Last Crusade)
Steven Spielberg hit the jackpot when he cast Sean Connery as the eccentric and overbearing father of none other than Indiana Jones, himself. The chemistry between Connery and Harrison Ford was instant and undeniable, and the two played off each other while stealing every single scene they were in.
Connery's wacky performance as Professor Henry Jones is also one of his most loveable and endearing. It will forever go down in history as one of the main highlights of the Indiana Jones film franchise.
Coolest: John Mason (The Rock)
This role could have gone south very fast, but director Michael Bay knew how to utilize Connery in an action movie role of this magnitude. His portrayal of Scottish supersoldier John Mason is one for the books, even though the actor was pushing 66 at the time of filming.
His on-screen chemistry with Nicholas Cage was a bit shaky at times, but Connery was clearly the one to watch. It's undoubtedly his most cool and suave performance next to James Bond.
Wackiest: Zed (Zardoz)
Audiences probably weren't ready to see Sean Connery in a fire engine red diaper and x-strap suspenders, but that's what they got with Zardoz way back in 1974. In many ways, Connery's performance feels out of place amidst the typical crazy 1970s sets and visual effects.
Still, that might have worked in his favor. Connery's performance as Zed showcases the character's common sense approach to what is obviously a bizarre revelation about the horrors of eternal life and the unending boredom it breeds.
Coolest: Jim Malone (The Untouchables)
Jim Malone is one of Connery's most memorable and recognizable roles by far. Nearly every fan can recite his quote regarding "the Chicago Way" with Connery's signature speech style. Beyond that, he churned out one truly excellent performance as the tough-as-nails cop determined to put Al Capone down for the count.
Although Connery had played several lawmen types in the past, his traditional actor's swagger and charismatic disposition made him perfect for the role which landed him several Best Supporting Actor nominations and straight-out wins. This was an amazing result given that The Untouchables was one of the most underrated action films of the decade.
Wackiest: Juan Sánchez-Villalobos Ramírez (Highlander)
Put aside the fact that Sean Connery is not, in fact, an Egyptian, and one can have a lot of fun watching his swashbuckling self on screen as the immortal Ramírez in the 1986 cult film Highlander. As both friend and mentor to Connor MacLeod, Ramírez stole the few scenes he was in thanks to his larger-than-life presence and outlandish outfits.
Connery would reprise the role for the much-loathed sequel in 1991, but his reappearance helped soften the blow a bit, thanks largely to his fish out of water character in an unrecognizable future world.
Coolest: James Bond (Various)
There was never any argument as to Connery's coolest role. He was the actor responsible for making James Bond a household name and an iconic movie franchise right up until this very day. Connery was smooth, sophisticated, brash, and traditionally masculine. Women loved him, and men wished they could be him.
Though some of his 007 performances haven't aged well—including the slapping of several female characters throughout his run—he was the man responsible for laying the foundation of the flawed secret agent's personality and mannerisms. What followed was a string of 007 hits that kept the globe-trotting MI6 agent in circulation for nearly 60 years. Hats off to Sean Connery, wherever he may be.