Cincinnati and New York: The Strobridge Lithographic Company
The image is a portrait of a man with "Matt. Keefe, America's greatest yodler" as the caption.
O'Brien (c. 1869-1954) began as the endman in Lew Dockstader's Minstrels. He appears as an actor in several quasi-Shakespearean productions and farces in the early years of the century, and went solo after 1915. A recording of him singing with James J. Corbett is available on "The Monarchs of Minstrelsy."