Take Me With You Dearie (1909)
A friend just sent me a link to Early Aviator, which has some great images of flight from the early 20th century. Some are serious photographs while others are fanciful illustrations of what aviation was to be.
Some of the sheet music imagery and titles feel like they could be part of a Mr. Show sketch. The image above is from sheet music published in 1909 by Junie McCree and Albert von Tizler, titled "Take Me Up With You Dearie."