The Penguin (Oswald Chesterfield Cobblepot)

First appearance: Detective Comics #58 (cover-dated December 1941 / on-sale date of October 21st, 1941 per the GCD):


And his entry from Who's Who:  The Definitive Directory of the DC Universe Vol. XVII (July 1986):

A few more pages from 1941's Detective Comics #58:




And from the story "Know Your Foes" in Detective Comics #566 (September 1986):

I was never really a Penguin fan in te old days, he just struck me as a dumb character. But I've become more interested in him since he effectively became DC's answer to the Kingpin, running the underworld from a distance from his Iceberg Lounge club!