Milton Grimm debuted in the cartoon series in the Chapter 1 webisode "The World of Ever After High", which premiered on May 30, 2013. He is voiced by Jamieson Price in the English version of the cartoon.
WebisodesBaba Yaga organizes an intervention to get Raven Queen back on the wrong path. Apple, Briar, Madeline, and Lizzie are invited to help, but with the exception of Apple, none are of use. The intervention is ended when a frustrated Raven accidentally turns the headmaster into a chicken-man. Milton fails to get Raven to sign the Storybook of Legends during the Legacy Day ceremony. Knowing what horror this could unleash onto their world, he sneaks off to think of methods to turn the tide. He is interrupted in his ponderings when a dark laugh comes from a mirror in his office.
WebisodesBlondie's influence over the students by asking her to broadcast about the truth of school legends. Unfortunately, none of the traditional legends hold true. Milton secretly manipulates the results to his liking, with disastrous personal consequences. Milton is writing a speech when C.A. Cupid barges into his office. He is surprised to hear her talk about True Hearts Day and tries to recover the book. He immediately squashes her ideas, forbidding her to speak of the dangerous holiday to anyone, lest it encourages students to break from their destinies. Milton asks questions when he sees C.A. Cupid, Briar Beauty, and Hopper Croakington II going around the school with supplies for a "play". Milton is interrupted during a web conference by Duchess Swan reporting a secret dance to him. Unfortunately, Duchess had been given the wrong directions, so she and Milton walk into a decoy location. Furious, the Headmaster gives Duchess detention. Milton refrains Raven Queen from playing in the Talent Show because Sparrow Hood has already signed up. Also, he is not impressed with her song choice. He attends the Talent Show and is in awe of Raven's capability. Milton agrees with Apple's new idea. Milton is angered by Raven's rebellious acts, but gets silenced by her. He walks around the halls.
TV specialsTrollsworth to switch the Evil Queen's Heritage Hall gift from a wand to a coin. Milton's plan is in action as he finds Raven by the Wishing Well, foreseeing a terrible vision. He is happy for Raven that she wants to sign. He is notified by Cedar that the book is a fake, but doesn't initially believe it. Later at night, he furiously questions the Evil Queen of where she hid the book, but she doesn't say much. He announces the Thronecoming dance and is soon confronted by Apple and Raven, who soon discover that it was he who made Raven into signing the book. He and Giles have a brotherly reunion and reconcile their relationship.
Milton walks past the castleteria unsuspecting. After hearing commotion in the castleteria, he finds that it was Ashlynn's stepsisters' idea to host a fashion show and cause a mess. As a result, they are pushed to clean it up. Milton is shocked to find that Baba Yaga's hut is storming the halls of the school. He, along with his brother, escort the students to the Legacy Orchard. The headmaster finds Hagatha strongly clinging to him. A croquet ball that Raven hits flies across the lake and bounces off his head in the process, scoring a goal. Milton presents the planting of the E-corn to his students.
He attends the Spring Fairest. Milton is vehement about the fact that the Wonderlandians entered Ever After, only to bring a fake Storybook of Legends. Wonderland questions.Milton appears behind Raven and discards the subject of Apple's
The headmaster advises for Raven not to touch her mother's mirror on visiting day. He shows up at where the Evil Queen is held to pronounce that visiting day hours are over. He supervises the dragon games and is turned into a frog by Faybelle. After the chaos is over, he returns back to normal form.