- “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 and run away. George promise a reward for the one who can find him. Robert, decide to take him back to his true family, know from Rumple that his son is in Pleasure Island. Pinocchio give an hand to Robert to find his son and Robert know finally the truth about his origin. While Pinocchio stops the Coachman and his minion, Robert and James run into King George who take back the child and give the order to kill Robert (that will be killed by Captain Hook). James (probably) ask to George more about his real parents and the King said that his family decide to give away James because he was the evil twin, from that moment, James grown as a evil knight.
Prince James 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 King George 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 to masquerade in his place.
After his death, his spirit is sent to the Underworld due to having unfinished business.
After the Third Curse
James becomes Sheriff of the Underworld and begins a relationship with Cruella after her death
James appears again in "Souls of the Departed". Stuck in the Underworld, James enters Granny's Diner where he finds 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 his wife is in the Underworld, so is his brother. He tells Mary Margaret to tell his brother that there is a new sheriff in town, and leaves.