James's parents Robert and Ruth cannot afford two sons, and is forced to give up James to Rumplestiltskin, who procures him for the childless King George. However, as a child, James is afraid to be a knight, and flees to Pleasure Island, where he is briefly reunited with his father Robert. Robert plans on taking him home, until they are found by King George who takes James back and has Robert killed, resuming his role as James's father.
Growing up as a prince and a knight and inheriting King George's lack of empathy and ruthless personality, James is apart of the siege against the giants at the Beanstalk in order to steal their riches and become wealthier. He goes there with an army, and a woman named Jack. However, Jack is fatally wounded with her own poisoned blade by a giant, and begs for James' help. James, unfazed, abandons Jack and leaves her to die.
Some time later, James meets his own death during a battle, and David must take his place.
When David meets Anton, the last surviving giant, he mistakens David for his brother James.
In the Underworld, James kisses Snow White, who mistakens him for David until James reveals his true identity. James tells Snow to warn David that he is the sheriff in this town, before leaving just as David arrives at the diner. Cruella eventually tells David that James has resented him his whole life, because James was given away and David wasn't, although when James finally confronts David he explains that he resents David for stealing his glory. James and Cruella plan on condemning Emma and Robin to the River of Lost Souls and using Robin's baby to bargain their way out of the Underworld, but a physical confrontation with David results in James tumbling into the hellish depths, trapped there for eternity, while Cruella manages to escape. After Hades departs, James's fate is unclear, as the rules change and souls begin to escape the River of Lost Souls.
Pinocchio writes about his time on Pleasure Island, including the time he met James and Robert.
- George (adoptive father)
- Robert Nolan (father)
- Ruth Nolan (mother)
- David Nolan (twin brother)
- Snow White (sister-in-law)
- Emma Swan (niece)
- Killian Jones (nephew-in-law)
- Neal Nolan (nephew)
- Cruella De Vil (lover)
- Jacqueline (ex-lover)
- James alludes to Prince Edward from the story The Prince and the Pauper.
- While taking his place, David took on the name James, like his brother.
Behind the Scenes
- The fight between James and Behemoth is similar to the fight between Oberyn Martell and Gregor Clegane from the novel A Storm of Swords.
- Both feature a duel with a prince and a colossal warrior, and while the prince manages to fatally wound the other and appears to have won the battle, he lets his guard down and therefore is brutally killed by his dying opponent.
- S1, E06: "The Shepherd" (flashback)
- S2, E13: "Tiny" (flashback)
- S5, E12: "Souls of the Departed"
- S5, E19: "Sisters"
- S6, E12: "Murder Most Foul" (flashback)