Jack's "At Least Four Ex-Girlfriends"
When Liz kicks Jack Sparrow out of her apartment she remarks that he has "at least four ex-girlfriends" to drunkenly impose on...
Where are they from?
So obviously, this is referring to possible ex-love interests for Jack Sparrow, but as this franchise has vastly outworn it's welcome I didn't know who these characters might be, and it turns out it could be quite a few people:
Part of our introduction to Jack is the reaction of several of his exes in the pirate haven of Tortuga, who immediately slap him upon seeing him again. The two ladies are cannonically called Giselle (played by Vanessa Branch) & Scarlett (played by Lauren Maher).
There are two characters in the tie-in prequel novel The Price of Freedom by A.C. Crispin that could qualify as ex-girlfriends, neither of which seem to have any images to share. The first is Esmerelda Maria Consuela Anna de Silva, a multi-racial spanish noblewoman turned pirate queen, and the second is Amenirdis, a slave that is revealed to be the lost princess of a mystic island.
It's never really established that Anamaria from the first Pirates movie ever actually had any romantic entanglement with Jack, but she's one of the female characters that slugs him upon seeing him again, so it's certainly implied. She's played, obviously, by Zoe Saldana, who would go on to establish herself as an action superstar all on her own.
The fourth Pirates movie features mermaids, and it's established that Jack has a history with one of them; a mermaid named Marina, played by actress Jorgelina Airaldi. Supposedly there's a deleted scene where they redo the slapping gag.
The fourth Pirates movie was the first to use Jack as the only protagonist, which means they needed to come up with a love interest exclusively for him. You can do a lot worse when creating an original character than to start by casting Penelope Cruz, but beyond the inspired casting Angelica feels a little color-by-numbers, a character built from pieces of Jack's personality for the sole purpose of giving him a female counterpart.
This may not actually count as an ex-girlfriend, but I'm including it because this is something that REALLY needs more bandwidth: The series of young adult novels depicting the adventures of a young Jack Sparrow feature a fellow young pirate named Arabella Smith, who goes on to have her own career as a pirate and frankly should have a whole series of movies all her own, because she's fantastic. If Disney is hell-bent on continuing the Pirates franchise, they should really consider just shifting the entire series to follow Arabella, because she rules. (she's never actually appeared in live-action. This image is a cosplayer named Lady Lafleur.)