Baloo von Bruinwald XIII (voiced by Ed Gilbert) is the main character of the story, based primarily on the sloth bear from Disney's The Jungle Book, but with a flight cap and a yellow shirt (and four-fingered hands instead of his Jungle Book counterpart's claws). Although lazy, slobbish, unreliable and always broke, as bears often are, he is also an excellent pilot and capable of the most daring maneuvers in the air, as bears often are not.He flies a cargo plane called the Sea Duck. He will also selflessly come to the aid of those in need of help. He also has a penchant for getting into schemes that require him to dress up in drag to suit the situation, such as when he became Rebecca's "female" co-pilot Tan-Margaret (a play on Ann-Margret) in "Feminine Air". Some of his mannerisms survive from The Jungle Book, including his nickname of "Papa Bear" by Kit, which Mowgli had given to him. In the episode "A Bad Reflection on You", Baloo gives his full name as "Baloo Bear" when introducing himself to a guard at Khan Tower. However, in the episode "The Balooest of the Bluebloods", it is revealed that Baloo comes from a prominent noble family and that Baloo's full designation is in fact "Baloo, Baron von Bruinwald XIII", though he himself had been initially unaware; raising the possibility that he was adopted. In this episode, he inherited 500 million dollars in the form of an extravagant estate, which was taken from him to settle the matter of his family's impressively long history of owing back taxes, thus restoring the status quo. Baloo only once mentioned any family, in reference to a gramophone record that had belonged to his father. He also calls Kit "Li'l Britches," as he did with Mowgli.
Kit Cloudkicker is 12-year-old navigator aboard Baloo's plane, the Sea Duck. His first appearance was in the pilot episode and introductory television movie Plunder & Lightning. He was originally voiced by Alan Roberts who did his voice for 9 episodes. R.J. Williams voiced Kit for the rest of the series. His trademarks are a green sweatshirt, a blue and red baseball cap worn backward and his ability to "cloud surf" (also referred to in the show as "cloud skiing"). The baseball cap was a gift to Kit from Baloo, as a sign of friendship and trust. In the episode "Flight School Confidential", Kit's height is revealed to be 3 feet 9 inches.
As a 12-year-old who lived with the air pirates under Don Karnage one year prior to the start of the series, Kit's character was a unique one in the history of Disney - he had a very dark past, partially because the storyline originally had him as being Don Karnage's protege. The story states that he left the air pirates because he "got sick" of them. He first encountered Baloo when he hid in the Sea Duck to escape from the air pirates because they were trying to find him His ambition was to become a pilot and to purchase his own aircraft.
Occasionally showing a selfish streak, Kit sometimes put his dreams ahead of those of his friends. Having lived on his own for most of his life, Kit's distrust of adults was apparent in the show. He warmed to Baloo only after being given the chance to fly the Sea Duck, and even then was ready to leave for greener pastures.
Nevertheless, he looked upon the other members of the "Higher for Hire" company as a surrogate family, affectionately referring to Baloo as "Papa Bear" on occasion. He clearly demonstrated his fondness for Rebecca Cunningham's daughter Molly on a number of occasions throughout the show, having been seen giving Molly "Piggy back" rides, and on one occasion rescuing her on his airfoil (the device Kit uses for cloud surfing - see below). Baloo gives him the same nicknames, such as "Little Britches", that was bestowed on Mowgli from The Jungle Book.
In the episode "Stormy Weather," Kit chastised Baloo saying "You can't tell me what to do! You're NOT my dad!" - This was a decision Kit would come to regret later in that episode.
Kit had the ability to cloud surf; using a crescent shaped metal device called an airfoil and a regular cord attached to the back of the Sea Duck allows him to "surf" in a similar fashion to someone water skiing, hence this is also referred to in the show as "cloud skiing". It was not made clear where Kit learned this skill, but he demonstrates at numerous times throughout the various episodes that he is incredibly adept at it. Baloo would often give his permission for Kit to tow behind the Sea Duck when appropriate, trusting in Kit's skill to let him have some fun. Baloo also had enough confidence in Kit to keep himself safe on the airfoil when separated and under attack, or when Kit had to be outside for something important. Outside of such situations however, he did not like Kit to take unnecessary risks, such as doing dangerous tricks or stunts.
Rebecca Cunningham (Sally Struthers), a petite brown bear with long brown hair in a french twist style, usually wears a white turtleneck sweater, and a purple-red jacket and matching slacks. Nicknamed "Becky," "Beckers," "Beck" (used only once in episode "A Star Is Torn") and/or "BC" (used once in "War of the Weirds") by Baloo which at first she highly resented being called, but soon grew accustomed to with affection (in return, she calls him "Fly Boy" on occasion). She is an unassumingly attractive, yet shrewd businesswoman with an MBA. Rebecca bought out Baloo's Air Service and his plane in the first episode (Plunder & Lightning) when the pilot failed to pay his bank loan and renamed it "Higher for Hire". Although she originally relegated herself to the administrative and sales functions of the business, the series shows she eventually learns to be a capable would-be pilot in her own right. Baloo's laziness and carefree attitude towards his responsibilities often infuriates her explosive temper, despite having some possible feelings toward him at times which does come up as a blistering jealous streak ("A Star is Torn"). Rebecca lives with her daughter Molly in an apartment in an upscale part of Cape Suzette (after episode S1:3), one which incorporates a waterfall in its design. She sometimes acts as a maternal figure for Kit.
Molly Elizabeth Cunningham (Janna Michaels), Rebecca's yellow-furred, 5-year-old daughter. An adventurous child who even at her age, is not afraid to speak her mind just like her mother, who's nicknamed her "Honey" and "Pumpkin" (while Baloo calls her "Button Nose"). Molly has a thing for her favourite ice cream brand "Frosty Pep"; sometimes pretends she is "Danger Woman" (the action/adventure heroine of a popular kids radio program) while seeking adventure along with Kit and Baloo. She carries a doll named "Lucy". She often outwits adveraries much older than her. Her middle name, Elizabeth, is revealed in "Mommy for a Day", and Molly is the only character to have any middle name revealed. No mention was ever made of Molly's father as series creator Jymn Magon reportedly said that Rebecca is either a widow or divorced, although at a 1998 U.S. fan convention Q&A online chat he did state in roundabout tones that she is actually divorced as originally written in the first TaleSpin press release.
Wildcat (Pat Fraley), a clueless and gangly lion who typically wears a mechanic's outfit. Although very childlike, he is ultimately a mechanical genius. For example; he can fix a smashed telephone in under ten seconds. He is infamous for being able to build the rare "overdrive" for airplanes. He has something of a lisp. Wildcat has a special place in his heart for dinosaurs as they are his favorite animal. He is also fond of pets and toys. He is honest and truthful, at times too truthful to annoy Baloo.