Sep. 14th, 2013
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According to Wikipedia, The Crime Syndicate's Owlman first appeared in 1964. This probably makes Richard Grayson the first Owlman, according to this quirky 1957 story, "The Grown-Up Boy Wonder!"
Note: Please adjust eyes for vintage comic reading!
Note: Please adjust eyes for vintage comic reading!

( Acrobatman Bonus! Extra Experience Points! )
Food for Thought: According to that big 'ol banner in that there header, Scans_Daily has been bringing the crack for a grand ten years now. So is it belated happy anniversary or advanced happy anniversary? Or is it a "don't count the years" thing?