Glasses Crow is the littlest member of the flock of five crows from Disney's 1941 film, Dumbo. Once Timothy and Dumbo first meet them, they are rude but when they hear Dumbo's sad story, they do everything they can to help him. They act as father figures to Dumbo. They are also notable for teaching Dumbo how to fly. The crows also sing the song; "When I See an Elephant Fly". Jim Crow refers to the other crows as brothers. There is no evidence given that the crows are related, so it is quite likely he means 'soul brothers', at the time, a term for close, lifelong friends.
Glasses Crow is generally childlike, innocent, and good-natured, albeit with tendencies towards jokes and teasing. He is fairly easy-going and friendly towards his friends and older brothers. He then proves himself to be an excellent mentor in helping Dumbo to fly, and is excited at the prospect of Dumbo returning to the circus with his new talent.
Glasses Crow first appears in the woods where he and his other brothers spot Dumbo and Timothy sleeping in a tree. He is utterly confused at the site, and so his leader, Jim Crow, flies down to investigate. Glasses laughs after Timothy and Dumbo fall into a pond, and they walk away. After a moment of thought, Timothy believes it and realizes that Dumbo's ears were perfect for flight. The Glasses Crow laughs at this and starts to sing the show stopper, "When I See an Elephant Fly". After the musical number and continuous laughter, Timothy gets angered and decides to give him a lecture of Dumbo's background and sad story. Glasses Crow starts to cry, regrets his mockery, starts to have sympathy for the two, and apologizes to them; explaining that they had seen the light. Gathering with the crows, Jim and Timothy form a plan that involves Timothy being given a feather from Glasses Crow. Timothy gives the feather to Dumbo, calling it a "magic feather" that will allow Dumbo to fly; in reality, it is merely a token to encourage and increase Dumbo's confidence. Glasses Crow takes Dumbo to a nearby cliff, where he attempts to take off. After the dust clears, he realizes that Dumbo is actually flying and excitedly proclaims that he has seen everything, thus, singing a reprise of his song, "When I See an Elephant Fly." Glasses sees Dumbo back to the circus and talks about how surprised the people will be to see Dumbo. Afterwards, Dumbo becomes famous as a result of his flying skills. Glasses Crow is later seen singing a final reprise of "When I See an Elephant Fly" and flying with his brothers and Dumbo, who is flying to a private train car that houses him and his mother (who was in solitary confinement earlier in the film and is now free after Dumbo's fame). Glasses waves good-bye to Dumbo and wishes him the best.
Who Framed Roger Rabbit
Glasses Crow makes a cameo appearance in the film. He is seen playing the background music of Jessica Rabbit's song "Why Don't You Do Right". He can also be spotted during the final scene, hidden amongst the crowd of toons.
House of Mouse
In the animated series House of Mouse, Glasses Crow appeared as one of the regular guests always flying with Dumbo. His most notable role is when Jim states he's seen nearly everything fly but he may never have seen Donald fly. Here, Glasses also make a cameo flying in the film Mickey's Magical Christmas: Snowed in at the House of Mouse.