Casino Royale (1954)
Starting things off weird, James Bond's first on-screen appearance was a made-for-TV adaptation. Played here by Barry Nelson as an American spy working for the CIA ("Combined Intelligence Agency", not the actual CIA for some reason?). Even setting aside the character's nationality, Nelson has none of the natural charm that Connery would bring to the role 8 years later in the film franchise. Still, the story is well paced enough to keep me entertained for its short 50-minute runtime. Edit: I forgot to mention the weirdest part! Bond orders a Scotch and water instead of a martini!
Dr. No (1962)
A lot of the tropes we've come to love started right here: the turn-to-camera shot opening the movie, the silhouetted dancers in the opening credits, the classic "Bond, James Bond" introduction, the shaken-not-stirred martini, and SPECTRE. The story gets off to a bit of a rough start with pretty hard shifts between the title, gun barrel shot, credits, and first scene, but from there on things feel more natural. With a modern eye, the story does feel a little stilted and it's funny to see what was considered to be such a sexual movie at the time, but really my only complaints are Dr. No himself and Miss Taro being played by English actors. Strangely, they did actually cast Asian people for the majority of the background flunkies. Overall, I did have a good time watching this one and I'm looking forward to the rest of this marathon.