Twelve O'Clock at Night

Malcolm Perret illustrated this 1923 sheet music cover.

That Old Gang of Mine

This cover, from 1923, resembles a motion picture lobby card in the way it is compartmentalized. I like how artist Malcolm Perret filled the lower left corner with an Art Deco swash for the dapper fellow to stand on. Also notice the drawing of the card game-- even though Prohibition was in full effect, the Old Gang appears to be drinking some bootleg booze.

And speaking of dapper guys, gotta love those "Beau Brummels of Song Land"!

All the names written on this cover suggest it was passed around a lot.

 

There's a Rainbow 'Round My Shoulder

Interesting trivia: Sydney Leff, the cover illustrator of this 1928 sheet music, died in 2005 at age 104. Irving Berlin, who published this, died in 1989, age 101.