Not much is known of Rebecca Cunningham's past, other than that she was once married and divorced from her former husband, and father of her daughter Molly. She mentions having grown up in a place with tons of snow in "Molly's Christmas" and in the first episode, it is stated she just came from business school.
Rebecca Cunningham is a strong independent woman who entered the business world to make some money. She is fairly responsible, often telling Baloo to be on time for his deliveries and to be more careful with the merchandise. She is very strict with Baloo and Kit especially since Baloo is a slob and she cannot stand slobs. However, deep down she truly cares for them to the point where, when Baloo is put up for ransom in "Save the Tiger", she sells her business, Higher for Hire, along with the Sea Duck to pay off his ransom, despite the business being extremely important to her. She even defends him against the insults of a bunch of potentially rich customers in "My Fair Baloo" when he saves them, telling them that while he is a slob, he is still a better person than all of them combined, showing she values her friendship with Baloo more than business and potential customers.
However, she is not without her faults. She places extreme importance on appearance, as shown in "A Touch of Glass", where she kicks out a potential customer because he looks like a slob and smells bad, though Baloo reprimands her for it, and informs her that the potential customer is worth half a million and extremely wealthy. However she refuses to listen, and when what appears to be a wealthy couple come in to hire the company, she doesn't suspect them when they accuse Louie of stealing their jewels and her purse (especially since Rebecca doesn't like Louie, as she finds him to be a slob as well), when in reality the pair is a couple of scam artists. In "Gruel and Unusual Punishment", she insists on Baloo losing weight for a party they are planning to attend, and in "My Fair Baloo", she asks him to touch up on his manners. This also coincides with her taste in men, as shown in "Molly Coddled" and "Her Chance to Dream", where in both cases, she falls in love with who appear to be gentlemen (though in the first case, the guy is a fraud who gets close to her in order to get his hands on a statue her daughter Molly keeps, while in the second case the man loves her, but is merely a ghost).
She can also be extremely stubborn. In "The Bigger They Are, the Louder They Oink", she refuses to listen to Baloo when one of her money schemes nearly gets them killed and she spends $250 on a wild pig that won't listen to her to find truffles, unaware that the natives might kill her. She finally admits that he was right all along, but that she just couldn't accept it.
In fact, some of the main plots of the episodes focus on her money-making schemes. Rebecca considers her business as a home and a living, while often handling the business, advertising, finding clients, and paperwork involving the business. She also gets so busy that she neglects Molly at times like in "Mommy for a Day" and in "The Incredible Shrinking Molly".
When Baloo fails to make a payment on his loan for his Plane, the Sea Duck, and his agency "Baloo's Air Service", the Bank sells the deed to Rebecca Cunningham (fresh out of business school). The bank recommends Baloo as a great pilot, so Rebecca desires to keep him on as her company pilot. Of course, all of this is hard for Baloo's pride to swallow, but after a harrowing run-in with Don Karnage's Air Pirates and the nefarious industrial magnate, Shere Khan, Baloo softens to Becky's (she hates it when he calls her that) offer.
Rebecca renames the service to "Higher for Hire" and has proven herself to be quite the savvy, stunning and ambitious businesswoman. She has a lot of business sense, cost-cutting measures, and all, and is always trying to come up with some new gimmick to attract business, some of which sometimes go wrong. Rebecca seems to constantly be lecturing Baloo about something (he's late, he's messy, he's lost the entire cargo).
Despite her stern demeanor, Rebecca is quite fond of Baloo and her other employees, Kit Cloudkicker, Baloo's navigator, and Wildcat, the agency's strange, but very gifted, mechanic. Subtlety betrays Rebecca in her affection for Kit, where she tends to treat him as though he were her own son (something Kit doesn't mind at all).
In the episode "When Chaos Comes Calling", Genie turns into Baloo, and flies off into the sky of Agrabah with the Zingalow. In this scene, he also transforms Jasmine into Rebecca, Abu into King Louie, and Iago into Kit.
She sometimes appeared in the post-show of Cinderella's Surprise Celebration to greet the guests.
She has not appeared in the parks since and is considered retired.
- Nicknamed "Becky", "Beckers", "Beck", and/or "BC" by Baloo, which, at first she highly resents being called, but soon grows accustomed to with affectioning return, she calls him "Fly Boy" on occasion.