Show creators Jymn Magon and Mark Zaslove were tasked by Disney to create a thirty-minute animated program with no set premise, and it was only near the pitch deadline that Magon hit upon centering it on Baloo from The Jungle Book, which had recently been theatrically rereleased.

The series was inspired by the show Tales of the Gold Monkey, which led the creators to have Baloo work for an air cargo delivery service, a concept also occasionally featured in Disney's DuckTales.

The character Rebecca Cunningham was directly inspired by Rebecca Howe from the sitcom Cheers, sharing her arc as an intelligent but inexperienced manager of a fledgling business, and the Baloo-Rebecca dynamic was fashioned after Sam Malone and Rebecca Howe.

The Louie's neutral bar location was inspired by Rick Blaine's bar in Casablanca, with the character Louie created as a stand-in for Rick, while the decision to add Shere Khan to the cast came later in development.

Magon and Zaslove also drew inspiration from Hayao Miyazaki's 1989 manga Hikōtei Jidai about a pig-headed seaplane pilot fighting air pirates; two years after TaleSpin premiered, Miyazaki released the anime Porco Rosso, which co-creator Zaslove felt took cues from TaleSpin.

Phil Harris, who voiced Baloo in the original Jungle Book film, was initially hired to reprise the role for TaleSpin, but at age 85 he had lost some comic timing and had to be chauffeured from his home in Palm Springs for each recording session; his work was ultimately discarded and Ed Gilbert took over as Baloo.

Famed Uncle Scrooge comic writer and artist Don Rosa wrote two episodes of the series, 'It Came from Beneath the Sea Duck' and 'I Only Have Ice for You'.

The pilot television movie Plunder & Lightning was the sole nominee for an Emmy Award for Outstanding Animated Program in 1991, though as a juried award it did not receive enough votes to win; the episode 'Last Horizons' proved controversial and never re-aired in broadcast syndication, and along with 'Flying Dupes' remains excluded from the Disney+ streaming release.