Originally, the role of Baloo was supposed to go to Phil Harris, who had voiced the character in the original 1967 film, The Jungle Book (1967). However, after one recording session, it was found that Harris, who was by then 85 years old, had aged to the point where he could no longer do the voice successfully and the role was performed by veteran voice actor Ed Gilbert instead.
Many of the planes featured in the series have real-life analogies: the SeaDuck is a Conwing L-16 Heavy Transport with Superflight 100 engines, similar to a Fairchild C-119 Flying Boxcar; the CT-37 Pirate Fighter is based on the Gee Bee Model R Super Sportster with a second pair of wings and pontoons instead of landing gear; and Louie's midair refueling plane is analogous to the Grumman G-21 "Goose".
DuckTales (1987) co-creator Jymn Magon always meant to develop a new series featuring Baloo as the main character and he simply welded that onto an unused idea from DuckTales (1987) about an air cargo service. The word "Tale" from the title and references to fowl in the aircraft names are a carryover from DuckTales (1987).
According to the series bible (guidelines handed out to episode writers), Don Karnage is based off of Kevin Kline's character in A Fish Called Wanda (1988). Kit Cloudkicker is based off of the Artful Dodger, the title character of Jonny Quest (1964), and the kid from the A Thousand Clowns (1965).
The family of the late Louis Prima (who voiced King Louie in The Jungle Book (1967)) sued Disney because Jim Cummings did too good of a job impersonating Prima when he voiced the character in this show. As a result, King Louie was completely absent from The Jungle Book 2 (2003) and was replaced by King Larry in House of Mouse (2001), the twin brother of Louie (also voiced by Cummings).
Early versions of the series had Kit Cloudkicker as Rebecca Cunningham's son, who longed for a father figure in his life. However, when the series decided not to answer the question of whether Rebecca was divorced or a widow, this was rewritten to Kit being an orphan and Baloo acting as a father figure and friend, similar to Baloo's relationship with Mowgli in The Jungle Book (1967).
Famed Uncle Scrooge comic writer and artist Don Rosa finished writing his episodes first, and presumably the first episode to get voice acting was Rosa's "I Only Have Ice For You" (pay special attention to Baloo - Ed Gilbert gives a different rendition of his voice here).
Rebecca Cunningham was considered a divorcée but it's implied that it doesn't matter whether she's a divorcée or a widow as long as the love/hate dynamic exists between her and Baloo. It's left to the audience to decide. It is also said that Rebecca inherited the cargo business from her father but this is changed entirely for the series pilot.
The relationship between Baloo and Rebecca Cunningham was inspired by Cheers (1982), at the time one of the most popular shows on television. Specifically, it was meant to mirror the love-hate relationship between protagonist Sam Malone (Ted Danson ) and his boss Rebecca Howe (Kirstie Alley ).
Initially was meant to be a spin off of DuckTales (1987) with Launchpad McQuack in the role that eventually went to Baloo. Disney decided to make it a stand alone series with characters from The Jungle Book (1967) after the success of the theatrical re release of the film in the early 90s. Launchpad McQuack was later featured on Darkwing Duck (1991).
Although the Thembrians are an obvious analogy to Stalinist Soviet Union, there is no equivalent of Nazi Germany in the TV series. However, one comic-strip story in the magazine Disney Adventures, had Baloo and Kit facing the Hausers, a dog nationality whose uniforms and military discipline is obviously resembles 1930s German styles.
According to the series creators, TaleSpin was a rush project in order to fill a gap in Disney's afternoon schedule as well as keep people from being laid off in the television animation department. The concept for the series came in the summer of 1989 (The Jungle Book (1967) being the film it was based off of because, when inflation was considered, it was the fourth-highest grossing Disney movie of that time) with the series being more or less fully developed by August 19, 1989. Voice acting for completed screenplays began in October 1989. The first episode aired, "I Only Have Ice For You", was shown in May 1990 as a sneak preview on the Disney Channel, with the series beginning regular airing in September 1990.
While the ABC series Tales of the Gold Monkey (1982) may have been an influence, TaleSpin was much more influenced by the flying scenes from Castle in the Sky (1986), written and directed by Hayao Miyazaki. The series creators wanted an outlet for such flying scenes which they had trouble trying to fit into DuckTales (1987). Ironically, Miyazaki may have been influenced by TaleSpin (1990) when he started work on Porco Rosso (1992) a few years later.