5) HMS Interceptor vs. Black Pearl in The Pirates of the Caribbean: Curse of the Black Pearl
After Will and Jack sneak onto the Isla de Muerta and interupt the Aztec ritual needed to lift the curse off Barbossa and his crew, Will helps Elizabeth run off with the medallion in the Interceptor, and Jack is left behind. As you can imagine, Barbossa isn't too happy that the medallion he's been searching years for is gone, so the Black Pearl chases down the Interceptor. Since the Black Pearl is the fastest ship in the Caribbean, it of course catches them and the battle begins. The Interceptor is out of ammunition so they load the cannons with boots and apples and forks, which does a bit of damage to the Pearl, to Jack's despair. But the cursed crew wins. They capture all the prisoners and the medallion and watch the Interceptor sink.
4) Kraken vs. Black Pearl in The Pirates of the Caribbean: Dead Man's Chest
Elizabeth, Will, Jack and his crew somehow make it off the Isla de Cruces alive, along with their jar of dirt, which Jack plans to use in a negotiation with Davy Jones. But when he realizes that there really is nothing but dirt in the jar, the crew turns to plan B: RUN! The Pearl outruns the Flying Dutchman and escapes their shooting range. But Jones isn't done yet. He sets his very friendly pet, the kraken loose on them. Will instructs the crew to load up all the rum. Jack shoots the floating barrels of rum, which explode, injuring the kraken. This buys them more time to escape. Pretty impressive to hold off on a sea monster that long, but it's only a matter of time. The crew gets into the one remaining longboat and sail away, watching the kraken devour the Black Pearl and it's captain.
3) Jack Sparrow vs. palace guards in The Pirates of the Caribbean: On Stranger Tides
Sadly, Pintel and Ragetti were not part of this battle, but it was still intense none the less. Jack lands himself a meeting with the king of England, King George II. King George wants Jack to lead Barbossa to the Fountain of Youth. Jack has other plans. Even though he's surounded by a whole palace full of guards, he manages to beak loose of the soldiers holding him down, swing on the chandelier, eat his cream puff, and get out. The king sends Barbossa and his men out to get Jack. But Jack is to clever for them. He hides in the tapestry, steals a very pudgy woman's earing, rides on top of her carriage, commandeers a cart of coal, and lands himself in front of a tavern, of course. Just when the thinks he's safe, another soldier appears, but Jack's father takes care of that for him.
2) HMS Dauntless vs. Black Pearl in The Pirates of the Caribbean: Curse of the Black Pearl
Barbossa and his cursed crew of the Black Pearl return to the Isla de Muerta to attempt to lift the curse. But once again, Jack returns in the midst of it. Meanwhile, Norrington and the Royal Navy are outside, ready to attack the Pearl. Barbossa and his men launch a very sneaky plan to take down the Dauntless that involves dresses and umbrellas. Pintel and Ragetti distract the Navy by rowing along the sea in a their pretty dresses. The rest of the crew sneak on board to kill the crew of the Dauntless. But Pintel and Ragetti get into a fight, revealing who they really are before the Navy had been finished off. The Navy fights back and holds off just long enough for Will and Jack to lift the curse inside the cave. The still outnumbered no-longer cursed crew of the Black Pearl is captured and their captain is shot. Quite the finale!
1) E.I.T.C. vs. Brethren Court in The Pirates of the Caribbean: At World's End
This amazing conclusion to the third pirates movie could hardly be better. It starts out with "Captain Swann" inspiring the crew to fight until the end and ends with the destruction of Lord Cutler Beckett's ship, the HMS Endeavour. First, the Black Pearl is sent out to battle the Flying Dutchman. This battle seems like the perfect time for a wedding, right? In the midst of fighting tons of sea creatures, Barbossa agrees to marry Will and Elizabeth, adding another element of romance to the battle. But their fairy tale comes to a close when Davy Jones stabs Will. Will has just enough time before he dies to stab the heart of Davy Jones, making himself captain of the Dutchman. After carving out his heart and locking it in a chest, Will returns with his new crew of the Dutchman and helps the Black Pearl demolish the Endeavour. With their two mains ships down, the armada of the East India Trading company surrenders to the Brethren Court and the Pirates live to tell another tale!