Errol Flynn is the granddaddy of swashbuckling adventures and sword fights. If you've never seen one of his films, you should Netflix one immediately! (I also recommend Captain Blood.) His final duel with the evil Basil Rathbone in Robin Hood is something to be seen, and set the precedent for all cinematic sword fights to follow.
2. The Dread Pirate Roberts vs. Inigo Montoya (The Princess Bride)
Take one cunning and relentless pirate, add in a Spaniard who has studied sword fighting his whole life, stir in some witty banter, and a mutual respect for each other's skill, and you have a recipe for one of the most fun and funniest sword fights ever. This battle is second only to Inigo’s sword fight of vengeance later in the film.
3. Darth Vader vs. Luke Skywalker (Star Wars: The Empire Strikes Back)
Okay, so they're lightsabers, not actual swords, but I think this still counts. When you start watching the Star Wars trilogy for the first time, this is the duel that you are just dying to see. Remember how scary, intimidating and evil Darth Vader was, the first time you saw these films? Remember how scared you were for Luke, the young, inexperienced, newly trained jedi? This is a pretty intense sword fight, complete with flying objects (courtesy of The Force) and it ends in a climax that no one saw coming...
I could go on for days about my love for this movie, but I will try to refrain. In this fairy tale (which is a good rival for The Princess Bride, by the way) a poor shopboy, Tristan, has gone on an adventure and along the way he was taught how to sword fight by Lightening Pirates (now doesn't that alone just intrigue you to go out and rent it?). This sword fight is hard to talk about, without giving away a fun plot point. Let's just say the fight choreography is imaginative, hilarious, exciting and unlike anything I'd ever seen before. I still marvel at it every time I watch it. 5. Rob Roy vs. Archibald Cunningham (Rob Roy)
I actually didn't care for this film, but it has one of the greatest sword fights in it, with one of the most evil villains I've seen on screen. Suffice it to say that Rob Roy's life throughout the first part of the movie has been like a bad country western song and Archibald is to blame for all of it. Rob Roy is an injured broken man. Archibald is smug and cunning. The fight goes for eight minutes on film, and the intensity is palpable; you feel every slash and parry of the swords.
8. Will Turner vs. Captain Jack Sparrow (Pirates of the Caribbean: Curse of the Black Pearl)
It has a pirate you want to love, a young hero you want to root for, and a donkey...what more could you ask for? Out of all the swashbuckling in this trilogy, the initial meeting of Will and Jack in the blacksmith's shop is still the best sword fight of them all. The use of the space is clever, both of their characters fight in a way that is a reflection of their personalities, and you're not quite sure yet who you should be rooting for. It's just pure fun!
9. Alejandro and Don Diego (The Mask of Zorro)
Not so much a sword fight as it is a training session, I love the scene in this movie where the retiring Zorro (played by Anthony Hopkins) schools the new Zorro (played by Antonio Bandaras) in the ways of sword fighting. There's some very fast and very well choreographed swordplay throughout this movie (and a story that isn't dumbed down for the masses). It lives up honorably to the Zorro tradition.
10. Connor MacLeod vs. Kurgan (Highlander)
This movie has it all: science-fiction, Scottish claymores, immortality, time travel. They're battling over control of the universe. And there can only be one...
Honorable Mention: King Arthur vs. The Black Knight (Monty Python and the Holy Grail)
'Tis but a scratch...
As I made this list, I noticed a pattern emerging. Yes, most of these fights are expertly choreographed, utilizing some amazing sets, and was filmed in the most artistic way, but the thing that I think makes them stand out the most is how emotionally charged they are. These fights all feature two complex and thoroughly fleshed out characters that have serious stakes on the line. There is so much more behind the encounter that informs the scene, and it is about more than just two people waggling swords at each other. This is film making at its finest. Be sure to leave me a comment and let me know which ones I missed (or ranked too low/high).