first I'll start with the cliches, I like the sea, treasure, grog, whiskey, rum, fast ships, mutiny when I'm the mutineer, I hate mutiny when it comes from the other end, wenches, and banannas (I am a monkey and all that.)
I'm also a fan of: reading(books, comic books, etc.) writing, drawing, music, hiking, treasure, grog. I know I already listed those last two but I really like them.
I'd like to meet:
I'd like to meet, any of the legendary pirates of old, so I could steal their treasure.
Any of the wonderful characters from Lucasarts' Monkey Island games, which shaped so much of life and raised me to want to be a monkey pirate.
The Three Headed Monkey.
I'd also like to meet any large poorly guarded merchant or cargo ships.
I would not like to meet the navy or coast guard, they're bad for business.
Music:
Rum Rebellion, Wages of Sin, The Pogues, far too many others.
Movies:
Pirates of the Caribbean. King Kong, Peter Pan, Hook, Muppet Treasure Island, Treasure Island, Captain Blood, Pirates of the Great Salt Lake
Television:
Pirates of Dark Water, Grim Adventures of Billy and Mandy, Invader Zim.
Books:
The Farseer Trilogy (shame the redship raiders lost though), The liveship traders.The Tawny man trilogy. The Voyage of the dawntreader, curious george, Treasure Island, His Majesty's Dragon, The Pirate Primer, Harry Potter, On a pale horse, THe chrestomanci novels, The Magid series, American Gods, Neverwhere, Stardust, Song of Ice and Fire, The Dresden Files, A Wizard of Earthsea, Tinker. The Abhorsn Trilogy.
Heroes:
Ioz, Captain Hook, The Demon/Zombie/Ghost Pirate Lechuck, Edward Teach, Stede Bonnet, Bartholomew Roberts. Donkey Kong. The Joker, Donald Duck, Green Goblin, Venom, Chistopher Chant, "Calico" Jack Rackam, Anne Bonny, Mary Read, Grace O'Malley, Guybrush Threepwood, Timmy the Monkey