1930s: The Lady Vanishes (1938) - Train films work for me
1940s: Rebecca (1940) - Many of my favorite films are from the 40s. Going with Rebecca because of the chemistry b/w Lawrence Olivier & Joan Fontaine. Judith Anderson as Mrs. Danvers is among the best villains. Notorious could have been listed too but will be going with a Cary Grant Hitchcock film in the 50s section (it is not North by Northwest but the other one).
1950s: To Catch a Thief (1955) - Cary Grant & Grace Kelly. The French Riveria. Can't ask for more but a glass of champagne.
1960s: Dr. No (1962) - Any 60s Bond film can be listed but the first one has a relatively high repeat value for me while scoring high on “Bondness” including the Caribbean as the location, a memorable villain & Bond girl, generous use of Bond theme, and so on
1970s: The Spy Who Loved Me (1977) - A film that pushes the boundaries whether it is the stunt in PTS, the car underwater, or the finale at Atlantis after the battle at Liparus. And Jaws.
1980s: The Living Daylights (1987) - Dalton's performance as Bond which is relatively closer to the book. John Barry's score. Also the last big cold war Bond film released during the cold war.
1990s: The World Is Not Enough (1999) - Brosnan's best performance. Sopie Marceau as Elektra King. M in the field. A good score & some nice locations around the Caspian Sea. Action sequences could have been better.
2000s: Casino Royale (2006) - One of the top Bond films. Craig is impressive on debut.
2010s: Skyfall (2012) - Bardem's performance as Silva, cinematography, & also because the other option is SPECTRE
2020s (so far): No Time to Die (2021) - The one and only release so far. Like how it uses the poison garden concept from the book "You Only Live Twice". Segments in Matera & the Caribbean are impressive, along with the action sequence in Norway where cars, bikes, and helicopters fly all over the place.