Which cartoon first introduced Chip and Dale as a pair?

Chip and Dale first appeared together in the 1943 cartoon Private Pluto.

The short places the two chipmunks in conflict with Pluto, who is guarding a military installation. Their mischievous behavior establishes the basic comic pattern that later defined the pair: they outwit a larger character while competing with each other as well.

At first, the chipmunks were not yet presented with the sharply contrasting personalities audiences later recognized. Their names and character traits became more distinct in subsequent cartoons, with Chip generally portrayed as the practical leader and Dale as the more impulsive partner.

Private Pluto is sometimes confused with later shorts that made the duo more recognizable, including Chip an’ Dale from 1947. That later film helped establish their familiar names and rivalry with Donald Duck.