As mentioned in a previous post, Rauner Library holds Abner Dean's papers. Dean (Dartmouth class of 1931) was a cartoonist whose work appeared in Esquire, Collier's, The New Yorker, and Life magazines. In the collection is a set of masks - one of which we know is of Franklin D. Roosevelt and was used as part of the illustration for the September 1932 cover of Life magazine.
Identifying the other masks is a bit trickier.
For example, this next one is probably Winston Churchill - or perhaps W. C. Fields.
And almost certainly Ed Wynn - the nose helps a lot here.
And we think this might be Truman Capote, though if this mask is a contemporary of the Roosevelt, that would be highly unlikely since Capote would have been 8 years old at the time.
But for the rest...well we're not sure. Let us know what you think!
guide to the collection is available.