One of cinema’s most iconic characters,James Bond has appeared in 27 filmsacross seven decades, being constantly re-imagined by new actors and fresh creative ideas. For all the innovation the epic action saga has seen, though, there is yet to be a 007 quite likeSean Connery’s original.

Appearing in seven Bond films across a tenure spanning 21 years, Connery utilized his smooth manner and effortless charisma to make Bond a surprisingly endearing action hero. His performances established spy-thrillers as must-see cinematic blockbusters, set the gold standard for what James Bond should be, and were the essential ingredient to making many of his Bond films quintessential films. Still, for all his triumphs in the role, not all of his movies are equally impressive.The best Sean Connery James Bond movies showcase his unique take on the role and all the debonair charm he brought to his performance.

Sean Connery as James Bond wearing a tuxedo and aiming his gun off-camera in Diamonds Are Forever

7’Diamonds Are Forever' (1971)

Director: Guy Hamilton

Serving as Connery’s firstreturn to the role afterGeorgeLazenby’sOn Her Majesty’s Secret Service,Diamonds Are Foreverhas come to be viewed as Connery’s worst Bond film. Carrying on from where Lazenby’s Bond flick finished, 007 avenges his murdered wife before investigating a smuggling operation in the international diamond market. There, he learns of Blofeld’s (Charles Gray) plot to weaponize the gems in a laser satellite.

There is some value toDiamonds Are Forever, especially regarding its stellar handling of the action sequences and a truly killer tune from the iconic Shirley Bassey;alas, much of the story doesn’t work. The characters fail to resonate and many of the actors didn’t pop off the screen—particularly a lazy Gray as Blofeld. Plus, the story’s focus on melodramatic beats and dull-edged comedy made for an underwhelming experience. Even Connery looked disinterested for most of the film, which is never a good sign for a James Bond movie.

diamonds-are-forever-film-poster.jpg

Diamonds Are Forever

James Bond infiltrates a diamond smuggling ring, uncovering a plot by his arch-nemesis Blofeld to build a space-based laser weapon. From Amsterdam to Las Vegas, Bond faces off against Blofeld’s henchmen and foils the plan, ensuring the diamonds return to their rightful owners.

Watch on Amazon

6’Never Say Never Again' (1983)

Director: Irvin Kershner

IfDiamonds Are Foreveris widely regarded to be Connery’s most underwhelming Bond film, then it’s only fair to say thatNever Say Never Againis his most polarizing. Featuring the then-53-year-old Connery’s unofficial return, it saw him reprise the role 12 years after his previous 007 outing and some 21 years since his James Bond debut. A bold-faced re-make ofThunderball,Never Say Never Againtracks an aging Bond tasked with engaging in spy games with SPECTRE as the criminal organization plots a devastating nuclear attack.

Never Say Never Againis not necessarily arewatchable James Bond watch, but it is an essential one, if only because of its sheer bravado. It doesn’t make much sense, especially as it stands outside the Eon Production’s canon and very much feels like an attempt at a Bond movie rather than a real one. While it has its fair share of critics,Never Say Never Againis a passably entertaining spy flickbolstered by an emphatic reminder as to why Connery is the definitive 007.

James Bond and Domino Petachi embracing at the pool in Never Say Never Again

Never Say Never Again

Watch on Max

5’You Only Live Twice' (1967)

Director: Lewis Gilbert

While most pundits would rankYou Only Live Twiceas the fifth best of Connery’s Bond films, the regard in which they view the film would change significantly. Alone in the vast chasm between the best and worst of Connery’s Bond flicks,You Only Live Twiceruns wild with a sense of adventure. This is largely thanks toRoald Dahl’s imaginative screenplay—yes, the man behindMatildaandCharlie and the Chocolate Factorywrote this—featuring volcanic fortresses and questionable moments, especially under a modern assessment.

Still,You Only Live Twiceoccupies a deft balance between upping the spectacle and steeping to parody, which both Bond purists and lovers of films like theKingsmanfranchise can enjoy, albeit for different reasons. With Bond having to stop SPECTRE’s scheme to see America and Russia engage in all-out war, it ensures the stakes remain high while injecting a new sense of humor into the franchise.A scene-stealing turn from Donald Pleasancealso makes this highly enjoyable.

never-say-never-again-poster-sean-connery-as-james-bond.jpg

You Only Live Twice

Watch on MGM+

4’Thunderball' (1965)

Director: Terence Young

The fourth Bond film ever made,Thunderballmay not quite have reached the level set by the first three installments, but it still ranks highly for lovers of the saga. With a dramatically ramped-up budget resulting in a boost of action bravado,Thunderballappealed to audiences and critics alike as an infectiously exciting blockbusterboasting large-scale adventure thrills in abundance.

With SPECTRE plotting to use NATO nuclear bombs to take over the world, Bond must thwart the organizations' plan before it’s too late. Brave, bold, and entirely captivating,Thunderballtouted one hell of a ride with some of the franchise’s best characters to boot. It took the franchise to the next level, proving Bond could do larger-than-life while still maintaining its essence.The campy and endlessly entertainingThunderballis one of the biggest and best Bond movies ever to grace the screen, with a never-better Connery at the center of it all.

Ernst Stavro Blofeld and James Bond talking in in You Only Live Twice

Thunderball

James Bond heads to the Bahamas to recover two nuclear warheads stolen by S.P.E.C.T.R.E. Agent Emilio Largo in an international extortion scheme.

Rent on Amazon

3’Dr. No' (1962)

A pioneering commercial accomplishment, a resounding critical success, and the jumping point of a cinematic dynasty,Dr. No’s influence cannot be overstated. It follows Bond’s investigation into the deaths of MI6 agents in Jamaica and his confrontations with an eccentric scientist wanting to destroy America’s space program.

In some respects,Dr. Nois surprisingly grounded. There is very little in the way of gadgetry, Q did not make an appearance, and the series' penchant for veering into fantasy was largely understated.Joseph Wiseman’snefarious Dr. Julius No does contribute to enhancing the eccentric surrealism later in the film. However,most ofDr. No’sappeal came from its unflinching action and Connery’s suave style, which proved to have a mesmerizing impact on audiences, both at the time and retrospectively.

A resourceful British government agent seeks answers in a case involving the disappearance of a colleague and the disruption of the American space program.

2’From Russia with Love' (1963)

Taking all the thrills and espionage excitement ofDr. Noand coupling that with a bigger commitment to larger-than-life exuberance,From Russia with Loveeffortlessly surpassed its already incredible predecessor. Transpiring at a frantic rate, it follows Bond’s mission to find a decoding device in order to ease Cold War tensions while combating SPECTRE at every turn.

From Russia with Love’spolitical inflections made for a particularly rousing action movie for its time, and it hasn’t lost any of its dare or flare in the decades since. Connery is more than comfortable in the role by now, joined by an equally impressiveDaniela Bianchiasthe iconic Bond Girl Tatiana Romanova. Aside from being one of Connery’s greatest Bond movies,From Russia with Lovestands tall among the greatest Bond movies ever made and a pinnacle of 1960s action.

From Russia With Love

1’Goldfinger' (1964)

Universally lauded as the definitive James Bond film,Goldfingerwas where so much of the Bond movie DNA either first appeared on-screen or cemented itself as a pivotal hallmark of the franchise. From its snappy wit and quotable one-liners to the wonder surrounding its gadgetry and its willingness to embrace more overt humor,Goldfingerinvigorated the Bond formula with even more style and fun.

It follows Bond as he investigates a gold smuggling rink and discovers powerful tycoon Auric Goldfinger (Gert Fröbe) plotting to raid Fort Knox and decimate the global economy.Goldfingeris a franchise-defining picture that cemented the Bond movies as the ultimate spectacle of fun, flashy action. The film remains highly regarded for nearly every aspect, from its plot to the memorable characters and Shirley Bassey’s legendary theme. Connery’s Bond legacy was already ensured, but this film ensured his place as a cinematic icon; indeed,Goldfingeris unequivocally the greatest Bond film ever made.

Goldfinger

NEXT:Every James Bond Actor, Ranked