Here's a few: 1932 Gottlieb Play-Boy, 1932 Gottlieb Five Star Final, non coin-op home edition. 1928 or so "IT"
The interesting thing about Play-Boy is that it has the 2 Free Play holes in each lower corner. It is absolutely original and not a hack. The only other 2 pictures I can find online don't have the Freeplay holes, neither does the ad for the game. I'm thinking it's really early or kind of late.
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