Rebecca Cunningham is the owner of Higher for Hire air cargo service and single mother to her 6 year old daughter, Molly. They live in an apartment in an upscale part of Cape Suzette, one which incorporates a waterfall in its design. She is the boss of her own pilot.
She's a brown anthropomorphic female bear with long brunette hair in a french twist style, typically wears a white turtleneck sweater, a magenta jacket and violet pants. When Baloo failed to make payment on his loan for his Plane, the Sea Duck, and his agency "Baloo's Air Service", the Bank sold the deed to Rebecca Cunningham (fresh out of business school). The bank recommended Baloo as a great pilot, so Rebecca desired to keep him on as her company pilot. Of course all of this was 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 softened to Becky's (she hates it when he calls her that) offer.
Rebecca renamed the service to "Higher for Hire" and has proven herself to be quite the savvy yet beautiful and ambitious business woman. 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 be constantly 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).
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 was put up for ransom in "Save the Tiger", she sold 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 defended him against the insults of a bunch of potentially rich customers in "My Fair Baloo" when he saved them, telling them that while he was a slob he was better than all of them combined, showing she values her friendship with Baloo more than business and potential customers.
Rebecca is not without her faults, as she places extreme importance on appearance as shown in "A Touch of Glass" where she kicked out a potential customer because he looked like a slob and smelled badly, though Baloo reprimanded her for this and informed her he was worth half a million and was extremely wealthy. However she refused to listen and when what appeared to be a wealthy couple came for a job, she didn't suspect them when they accused Louie of stealing their jewels and her purse (especially since Rebecca doesn't like Louie as she finds him a slob) when in reality the couple were scam artists. In "Gruel and Unusual Punishment", she insisted Baloo lose weight for a party they were going to attend and in "My Fair Baloo" asked him to touch up on his manners. This also coincides with her taste in men, as shown in "Molly Coddled", & "Her Chance to Dream", where in both cases, she fell in love with who appeared to be gentlemen (though in the first case the guy was a fake who got close to her to get the statue Molly had while in the second case the man loved her but was a ghost).
She can also be extremely stubborn. In "The Bigger They Are, the Louder They Oink", she refused to listen to Baloo when one of her money schemes nearly got them killed and she spent $250 on a wild pig who wouldn't listen to her to find truffles, unaware the natives would kill her. She finally admitted he was right 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, client finding, and paperwork involved with the business. She also gets so busy that she neglects Molly at times like in "Mommy for a Day" and "The Incredible Shrinking Molly".
Skills and abilities
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.
Rebecca is Molly's devoted mother, but often struggles with juggling the responsibilities of being both a single parent and a businesswoman. Sometimes, Molly has shown to be sharper than Rebecca like in "Molly Coddled" when Rebecca started dating Covington, Molly was hostile toward, and while Rebecca probably only thought Molly was just jealous or mischievous, Molly was actually aware there was more to Covington than meets the eye.
While the two are polar opposites in more ways than one, they are close friends, with hints at times of mutual attraction. In "It Came From Beneath the Sea Duck", Baloo reluctantly accompanies Rebecca on a shopping spree. In “Stormy Weather" Rebecca expresses horror at the idea of her and Baloo as a married couple. In "Her Chance to Dream", Baloo becomes slightly jealous when Rebecca is courted by the ghost of a Victorian era sea captain.
In the beginning of "A Star Is Torn", the two have a dinner date as "friends". Baloo's statement to Rebecca of "Remember the last time we went out?" suggests that this is not their first date. In "Feminine Air", when Rebecca reveals that she could tell her co-pilot "Tan Margret" was really Baloo in drag, she calls Baloo her "best friend". In "Gruel and Unusual Punishment" both Baloo and Rebecca ready themselves to go to the annual Pilot's Ball with her getting a new dress (which is a leftover from "Her Chance to Dream") and him losing weight when she threatens to take someone else and they get just a little bit closer (but not a lot) in the closing moments of "My Fair Baloo".
In addition, at the end of "Last Horizons", Rebecca clearly shouts with joy at Baloo's escape from certain death, "I love you, Baloo!". Their relationship can also be fairly antagonistic, with Baloo resenting his status as Rebecca’s employee and her ownership of his plane, while Rebecca is disdainful of Baloo’s irresponsible actions and tendency to lie in order to get out of trouble.
As Baloo's navigator, Kit is Rebecca's employee, and he shows a great deal of respect for her as a boss. Their relationship is somewhat deeper though, with Rebecca showing almost motherly concern at times for Kit. As a result, any misbehavior of his-whether real or perceived-is quick to move her to anger out of her worry for him.
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I won't take no for an answer!
I'll prove to you (verbs) even if it kills me!
I'll strangle him! Then I'll fire him! Then I'll strangle him again!
Land now you idiot so I can strangle you!!
If you'd just listen to me Baloo, we could turn this business into a money maker!
- Nicknamed "Becky," "Beckers", "Beck" ("A Star is Torn") and/or "BC" ("War of the Weirds") by Baloo which at first she highly resented being called, but soon grew accustomed to it, she calls him "Fly Boy" on occasion.
- Despite having a daughter, nothing is said about who her husband is, although in the comic The Long Flight Home, it is revealed she was widowed.