It's in the Air ★★★

Con-man Jack Benny, visiting estranged wife Una Merkel, becomes the pilot of a ballon that will attempt to reach the stratosphere. Benny’s reward for the feat is $85,000, if he survives.

The cool, self-assured, and fast thinking confidence man was not a typical character role for Jack Benny. This film was made before he established the miserly, boastful, and somewhat incompetent persona he played on radio.