1) Dr No - the one that really established it all. Funny enough, I don't think it ever gets the credit it deserves - overshadowed by From Russia with Love, Goldfinger, Casino Royale or On Her Majesty's Secret Service. Absolutely, there would be bigger budgets, memorable moments to come - but the template of Bond as a sophisticated, debonair assassin was struck from the first film, a magical accident of Sean Connery, Ian Fleming, Terence Young, Ken Adams, Broccoli/Saltzman, etc coming together. Connery proved stunningly right as Bond, the story was excellent (it's a good fall back structure to borrow even now), Joseph Wiseman an expert villain, Ursula Andress an incredible Bond. A sidekick, a treacherous girl, combination of comedy and violence... It was there from the get go.
2) Goldfinger - for many this is THE Bond film, even now, a beautifully structured piece of entertainment, with perhaps the best villain, best use of gadgets, best theme song, and best plan of all time. Terrific fun.
3) On Her Majesty's Secret Service - the first Bond without Connery, the first box office disappointment, the first unhappy ending... and now many (myself included) see it as the greatest Bond of them all... I'd say it comfortably has the biggest "cult" of any Bond film.
4) Live and Let Die - Diamonds Are Forever restored the box office health of the Bond films, but a lot of that was attributed to Connery. Live and Let Die showed the series could thrive with a new Bond if that Bond was a better established actor - and few had the pedigree of Roger Moore, whose Saint TV series was an excellent training ground for the part. It's a flawed movie that hasn't aged very well, but its rock soundtrack is superb and there are some good moments.
5) The Spy Who Loved Me - Harry Saltzman's financial problems resulting in him leaving the series, and this showed that Cubby Broccoli could handle things fine on his own very much thank you with a movie that admittedly pinched most of its key elements from earlier films (Russian agent female lead, spectacular villain, wordless henchman) but rehashed them to a brilliant degree, making it an artistic high point of the Bond rein.
6) Goldeneye - the Bonds took their longest break before Pierce Brosnan showed their was life in the series yet. I don't think anyone remembers this film with that much fondness, but it was a well made entry which revitalised things.
7) Casino Royale - a major shot in the arm, Daniel Craig being the best challenger to Connery's crown. It's an origin story though oddly the film didn't need to be.
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