A rousing and triumphant series that brought swashbuckling adventure to the modern day with plenty of action, fantasy, and romance to boot, the Pirates of the Caribbean movies are a hallmark of 21st-century cinematic entertainment. Captain Jack Sparrow stands as one of the most iconic characters in cinematic history, with his irreverent scheming, deceitful manner, and eccentric physical comedy all emblematic of the series’ sense of fun.
Moreover, Pirates of the Caribbean has plenty of terrific characters who are central to the epic fantasy adventure’s enthralling entertainment value, ranging from daring heroes to nefarious villains and everything in between. The dynamic between many of the saga’s most iconic characters has defined its comedic highlights as well as its dramatic tension. These duos are the best pairings in the Pirates of the Caribbean movies, contributing to their ongoing popularity.
10 Will Turner and Bootstrap Bill (Orlando Bloom and Stellan Skarsgård)
“I’ll find a way to sever Jones’ hold on you and not rest until this blade pierces his heart.”
One of the central subplots of Pirates of the Caribbean: Dead Man’s Chest focuses on Will Turner’s (Orlando Bloom) reunion with his father, Bootstrap Bill Turner (Stellan Skarsgård), as he works as part of the crew of the Flying Dutchman. While Will initially boards the ship in exchange for Jack giving him his compass, he quickly forms a bond with his father and promises to free him from his service.
Given Bootstrap was something of a mythic figure in the first film, seeing him not only brought to the screen but also given strong character work with his son helped make Dead Man’s Chest such a rewarding sequel. Will later makes good on his promise, becoming the new captain of the Flying Dutchman and making Bootstrap a free man, though his father relinquishes the offer to sail with his son. Will and Bill’s bond is unexpectedly sweet but complicated, and both actors do a great job bringing it to life.
9 Jack Sparrow and Hector Barbossa (Johnny Deep and Geoffrey Rush)
“Me, I’m dishonest. And a dishonest man you can always trust to be dishonest, honestly.”
It isn’t unusual for heroes and villains to make such compelling pairings, especially when they have such a history as Jack Sparrow and Hector Barbossa (Geoffrey Rush) do. Besides, it’s questionable if Sparrow counts as a true movie hero. Regardless, this protagonist/antagonist duo is one for the ages. Imbued with a venomous vendetta, Jack Sparrow is introduced as a man hellbent on killing Captain Barbossa and reclaiming his beloved ship.
They are hilariously spiteful of one another, but the humor between them never interferes with the bitter feud that underscores much of the first movie. Later reunited as reluctant allies, Sparrow and Barbossa eventually relax their bitter antagonism, even if a competitive rivalry remains firmly intact. The frenemy brilliance of the duo was largely responsible for all the entertainment value in the saga’s latter movies, Pirates of the Caribbean: On Stranger Tides and Pirates of the Caribbean: Dead Men Tell No Tales.
8 Jack Sparrow and Elizabeth Swann (Johnny Depp and Keira Knightley)
“Welcome to the Caribbean, love.”
One of the most underrated duos in the Pirates of the Caribbean movies, Jack Sparrow and Elizabeth Swann (Keira Knightley) share a tumultuous and backstabbing relationship from the moment they meet. Mere moments after saving her from drowning, Jack has a knife to her throat as he is threatening her life to escape imprisonment. While mutual respect between the two blooms, the dynamic between them, delightfully, changes little.
The relationship isn’t without its hitches. Elizabeth leaves Jack for the Kraken in Dead Man’s Chest and burns the rum when they are deserted on the island together. However, they do ultimately help each other out through a shared sense of self-interest, like when Jack casts the decisive vote for her as Pirate King in Pirates of the Caribbean: At World’s End. Their encounters go a long way to defining Elizabeth as her own character as well, particularly through her ability to manipulate and outwit Jack like few others.
7 James Norrington and Elizabeth Swann (Jack Davenport and Keira Knightley)
“Our destinies have been entwined, Elizabeth, but never joined.”
Destined to be wed at the beginning of The Curse of the Black Pearl, the failed romance between James Norrington (Jack Davenport) and Elizabeth Swann makes for one of the best character pairings in the franchise. Both characters have their lavish lives completely uprooted when Jack Sparrow waltzes into Port Royal, closely followed by Captain Barbossa’s undead crew, who kidnap Elizabeth, leading Norrington to launch a rescue attempt.
Funnily enough, the duo becomes far more enjoyable in Dead Man’s Chest, when Elizabeth has set her heart on Will Turner and Norrington has found solace for his past failures in the bottle. The coarse earnestness yet residual affection between them offers a refreshing dynamic to the sequel that its predecessor didn’t have. However, Norrington’s love for Elizabeth remains, as evidenced in At World’s End, when he sacrifices his life to spare her from the Flying Dutchman in one of the sadder scenes in the franchise.
6 Murtogg and Mullroy (Giles New and Angus Barnett)
“There’s no real ship as can match the Interceptor.”
A joyous duo throughout the Pirates movies, Murtogg (Giles New) and Mullroy (Angus Barnett) mark a small yet important pairing that has a unique ability to bring a smile to viewers’ faces. The two bumbling and argumentative guards are introduced in The Curse of the Black Pearl as Royal Marines guarding the Interceptor, who confront Jack Sparrow when he tries to board the ship.
While the pair is sadly absent from Dead Man’s Chest, they return for the following three movies. At World’s End sees them again getting swindled by Jack Sparrow as they enter into a fierce debate with one another. The last audiences see them is in Dead Men Tell No Tales, ultimately sailing as part of Jack Sparrow’s crew aboard the Black Pearl. As two brilliant comic relief characters who also make for handy exposition dumps, Murtogg and Mullroy make for a wonderful pairing as two fan favorites whose mere presence makes the Pirates of the Caribbean movies so rewatchable.
5 Jack Sparrow and Joshamee Gibbs (Johnny Depp and Kevin R. McNally)
“Take what you can.” “Give nothing back.”
As a deceitful trickster prone to betrayal, manipulation, and flat-out lying, it stands to reason that Jack Sparrow has few true friends. Perhaps his only one is Joshamee Gibbs (Kevin R. McNally), a former Royal Navy sailor who served as Jack’s first mate before the mutiny on the Black Pearl and remains his steadfast supporter and most trusted accomplice.
Loyal to a fault, Gibbs is not only Sparrow’s most dedicated ally but also a pivotal figure in his leadership, often keeping the crew in line even when Jack’s sporadic schemes invite doubt among those serving under him. Epitomizing the honor among thieves mantra and the notorious Pirate Code, the duo is always united in their endeavors to rip other people off, as evidenced by their mottos, “Take what you can” and “Give nothing back,” two of the most famous quotes in the Pirates movies.
4 Ragetti and Pintel (Lee Arenberg and Mackenzie Crook)
“‘Ello, poppet.”
Few franchises have had a litany of memorable and beloved side characters like what Pirates seems to flaunt so effortlessly. As two ragtag pirates introduced in The Curse of the Black Pearl as members of Barbossa’s crew, Ragetti (Mackenzie Crook) and Pintel (Lee Arenberg) are always ready to inject some comedic lightness into the films. The squabbling seafarers are an ever-present party on the adventures of Captain Jack Sparrow, Will Turner, and Elizabeth Swann.
For all their bickering and trading of insults, the duo is the very model of friendship in the Pirates movies, winning over millions of fans as their endearing silliness beautifully complements their coarse pirate personas. Completely inseparable from the moment they are introduced, it is a small yet noticeable and unbecoming tragedy that the characters didn’t return to the franchise after At World’s End.
3 Jack Sparrow and Will Turner (Johnny Depp and Orlando Bloom)
“Not all treasure is silver and gold, mate.”
The relationship between Jack Sparrow and Will Turner gets off to a rocky start, with the two dueling in Turner’s blacksmith store. Later, Turner frees Jack from jail to begrudgingly enter into a partnership that will help him rescue Elizabeth Swann. With the two seafarers often betraying one another, it is to the delight of viewers that, while their bond grows stronger, the scheming nature of their pairing never changes, something that helped make The Curse of the Black Pearl an unexpected box office triumph.
Despite all the backstabbing antics, Sparrow and Will have an uncanny tendency to show up precisely when the other needs them most, be it when Jack is facing the gallows or when Jack prevents Turner’s death by stabbing the heart of Davy Jones (Bill Nighy) in At World’s End. As dysfunctional as they are, Jack Sparrow and Will Turner’s uneasy alliance is an enthralling and entertaining core to the first three Pirates of the Caribbean movies.
2 Will Turner and Elizabeth Swann (Keira Knightley and Orlando Bloom)
“Will, how many times must I ask you to call me Elizabeth?”
For all the dark fantasy intrigue and the swashbuckling action-adventure spectacle, Pirates of the Caribbean ultimately finds its beating heart in the romance between Will Turner and Elizabeth Swann. Swann is the daughter of a governor, and Turner is the orphaned apprentice to a blacksmith; thus, it initially seems as though their mutual feelings will never come to fruition. Their situation changes when Captain Barbossa’s crew storms Port Royal and abducts Elizabeth, leading Turner to embark on a daring quest to rescue her.
Their dedication to one another is made abundantly clear throughout the first film, so when they are able to spend more time together in Dead Man’s Chest, their romantic scenes are rewarding and earned. Finally marrying amid a battle in At World’s End, Will and Elizabeth’s love story is the beating heart of the original trilogy. Their reunion at the end of Dead Men Tell No Tales, with Will’s curse broken, presents a thoroughly rewarding conclusion to the film series.
1 Jack Sparrow and The Black Pearl
“Now, bring me that horizon.”
Han Solo has the Millennium Falcon, James Bond has his Aston Martin, and Captain Jack Sparrow has the Black Pearl. As unconventional as it may be, there is no pairing in the Pirates franchise quite like Jack and his beloved vessel, a ship he has to fight to retrieve and stay in charge of as he clashes with other pirates who want to captain it to the bottom of the ocean. As such, it perhaps isn’t all that surprising that Sparrow shows more sentiment, love, and loyalty to the Black Pearl than he does to most of the other characters in the series.
Like many of the most famous vehicles in cinematic history, the Black Pearl itself is imbued with a distinct personality that makes it feel like a character to the audience that truly belongs with Jack Sparrow at its helm. While he wins it back and loses it multiple times throughout the five movies, it is another triumph of the finale of Dead Men Tell No Tales when Jack Sparrow sets off into the sunset as the captain of his cherished ship.
