Robert Woolsey was terminally ill and suffering from kidney disease during filming, as he had during the previous film, On Again-Off Again (1936). He struggled to complete High Flyers and died less than a year after its release.
The censors would not allow Wheeler and Woolsey to become high from the cocaine in the movie. Instead, the word "cocaine" was changed to a euphemism to meet Production Code requirements.
The play, "The Kangaroos" by Victor Mapes, opened in New York City in 1926.
Wheeler's impersonation of Charlie Chaplin in this movie was also a big part of his stage act before he teamed up with Woolsey. Chaplin greatly appreciated and admired Wheeler's take-off on him.