|“||You are not trying hard enough.||„|
|~ The Shadow|
|“||Neverland is a place for children to visit in their dreams, not a place for them to live. You were the first to try and stay, and in doing so... you're breaking the rules!||„|
|~ The Shadow to Malcolm|
The Shadow is voiced by singer Marilyn Manson.
Malcolm and his son, Rumpelstiltskin arrived in Neverland, and met the Shadow, ruler of the island. Malcolm first met the Shadow and he asked it to make him fly. The Shadow said he needed to believe in himself. The Shadow also showed a young Rumplestiltskin what his father had become. It then abducted Rumpelstiltskin and took him back to the Enchanted Forest. The Shadow promised Malcolm eternal youth, but not immortality, because immortality was impossible to have for mortals. But Malcolm said he would find a way to become immortal. Malcolm renamed himself Peter Pan and set about abducting young boys to Neverland, where they became the Lost Boys, slaves of the Shadow and Peter.
Many years later, One night while Rumplestilskin's son Baelfire was in London with the Darling family, The shadow traveled to their house and took Wendy to Neverland, despite Baelfire's warning not to go with him. However, the Shadow returned her as it didn't want her anymore. She told Baelfire how terrible it was for the children at Neverland and that the shadow was coming back for one of her brothers. Baelfire and the Darlings then prepared for the Shadow's arrival. The Shadow arrived and Baelfire told it to take him instead and not to bother the family again. The Shadow agreed and took Baelfire to Neverland. On their way there, Baelfire struggled and the Shadow eventually lost him as he fell into the ocean near Neverland causing the Lost Boys to come look for him.
The Shadow appears many years later as Greg and Tamara arrived in Neverland with Henry. Felix, Peter Pan's right-hand man, demanded that they hand over Henry. They refused and Felix has the Shadow kill Greg while Henry and Tamara fled.
The Shadow later constantly appears to Rumpelstiltskin in the form of Belle in order to trap him until he was found out by Regina and he fled afterwards. After Pan's supposed defeat, Regina later bounds the shadow to the Jolly Roger's mast in order to go back to Storybrooke. It is later released by Pan while he was in Henry's body. He then attacks Mother Superior and takes her shadow. While Pan was casting his curse, the shadow attacked David, Hook, Tinkerbell, and Neal while they were at the chapel. It dies as it is trapped in a candle in a coconut by Tinkerbell.
- The Shadow acts as the Bigger Bad in Season 3a because, even though he rules Never Land and acts as Peter Pan's boss, he's not directly involved in the plot.
- The Shadow is similar to Ryuk from Death Note; they are supernatural entities who are indirectly responsible for the plot of their respective storylines (The Shadow granted Malcolm eternal youth, thus turning him into Peter Pan; Ryuk gave Light the Death Note, which drove Light to use it to become god of a new world by purging crime).