- “You stole my glory. You were never half the man I was and yet you got everything. Everything that was mine.”
- ―Prince James to his brother David
Prince James was the twin brother of Prince Charming, a character on ABC's Once Upon a Time. He is portrayed by starring cast member Josh Dallas, and does not have a Storybrooke counterpart. He is the biological son of Ruth though was given up to King George and his wife, who couldn't have children.
Before the First Curse
Prince James is born to Ruth and her husband Robert, along with his twin David. He is traded to Rumplestiltskin to save the family farm. Rumplestiltskin gives the infant to King George, who needs a heir due to his wife being barren and unable to conceive a child. King George names him James and raises the child as his own.
However, James doesn't like the prince life or George's plans to make him a killer and runs away. George, believing he was abducted, promises a reward for the one who can find him. Robert, deciding to take him back to his true family, learned from Rumple that his son is on Pleasure Island. Pinocchio gives him a hand to in finding his son and James learns the truth about his origins. While Pinocchio distracts the Coachman and his minion, Robert and James flee, only to run into King George. After Robert defiantly refuses the reward or to hand over his son, George has his men murder him while covering it up as an accident. With that, James remains as prince, with his morality tainted by George's corrupt influence.
Prince James grows up to be spoiled and irresponsible. He pursues a romantic relationship with Jacqueline, but King George wants James to focus on helping the kingdom, as it is in economical disarray. James and Jack go after the giant, Anton, and they give him a magical mushroom that shrinks him to human size. Jack and James take him to a tavern where Anton enjoys music. Jack tells Anton about the kingdom debts, and Anton decides he wants to help the kingdom with gold by giving them treasure. However, they betray Anton, and climb up the beanstalk to fight a battle to slaughter all the giants and steal their beans. Jack stabs Arlo with her poisoned sword, and he does the same to her. Dying of her the stab wound, Jack calls to James for help, but he refuses to save her and hastily leaves to climb down the beanstalk after gathering a bag of treasures. Anton is the only survivor of the massacre.
Much later on, Prince James spars with Behemoth in a sword fight. After winning the match, the prince meets with King George and King Midas. The three come to an arrangement wherein if the prince can defeat a dragon that has been ravaging Midas' kingdom, Midas will supply George's kingdom with gold using his golden hand, which turns any object into gold upon contact.
After Midas has departed, Behemoth unexpectedly rises and stabs the prince through the torso, killing him. This event necessitates the grieving King George into making an additional deal with Rumplestiltskin. He trades the whereabouts of the Fairy Godmother to the wizard in exchange for the dead prince's twin brother to masquerade in his place.
After his death, his spirit is sent to the Underworld due to having unfinished business. Somehow, he learns how his brother took his place, growing resentful.
After the Third Curse
James becomes Sheriff of the Underworld and begins a sexual relationship with Cruella after her death.
Stuck in the Underworld, James enters Granny's Diner where he finds his sister-in-law Mary Margaret. Mistaking him for his brother David, she asks why he changed his clothes and he kisses her. He reveals his identity and realizes that if Snow's in the Underworld, so is David. He tells Mary Margaret to tell his brother that there is a new sheriff in town, and leaves right as his twin comes in to catch a glimpse of him.
Weeks later, James ambushes David as he's bringing supplies. David is apprehensive as Cruella hinted that James resents him for being chosen to be kept by their parents. The underworld sheriff reveals that the diva was wrong; he really angry his brother stole his identity and got everything he would've had if he wasn't killed. He tasers David and locks him in the sheriff station and impersonates him. His disguise easily fools Emma and once they meet up with Robin and his baby daughter, he slaps a cuff to limit her magic. It was all part of a plan by him and Cruella to use the newborn as leverage against Hades (as he's in love with the infant's mother) in order to return to life since the Author, James' great-nephew, refuses to do so. Before James can sentence his niece to eternity in the River of Lost Souls at the harbor, David comes to the rescue with Captain Hook. While Cruella retreats, the twins have a fist fight with David having the upper hand. He tries to reason with his embittered sibling that he can help him move on and find peace, but James exclaims that the former's death is his unfinished business. Refusing to escape with Cruella, he tries to stab his brother with a knife hidden in his sock. But David redirects his movement, sending him off the edge of the pier. The vengeful prince plummets to into the river and dissolves into it, much to his brother's dismay.