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DC Jan 1944

Detective Comics #83

Detective Comics #83
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1st appearance of Alfred with a thin build as commonly depicted
Alfred departs for vacation after lamenting his excess weight and upon his return at the end of the story, he is more recognizable as the character that has endured through the decades
Batman's underground hangar is first referened to as the Bat Cave
DC Feb 1951

Detective Comics #168

Detective Comics #168
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Origin of the Joker, formerly a crook named the Red Hood who pulled a heist that led him through a vat of chemicals that caused his clown-like appearance
DC Dec 1955

Detective Comics #226

Detective Comics #226
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2nd appearance and origin of Martian Manhunter
Batman reveals that he operated under the Robin moniker when he was a boy
1st appearance of Harvey Harris, an early mentor of Bruce Wayne
DC Dec 1961

Detective Comics #298

Detective Comics #298
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1st appearance of the second Clayface, Matt Hagen, a scuba diver who had come into contact with a clay-like substance that compromised his molecular structure
[October 2024 - Alan Tudyk will voice Clayface in Creature Commandos / November 2024 - a Clayface movie is in development with writer Matt Flanagan (The Haunting of Hill House)]
DC May 1977

Detective Comics #469

Detective Comics #469
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1st appearance of Doctor Phosphorus, a villain who is perpetually on fire after being exposed to massive amounts of radiation
1st appearance of Rupert Thorne, a corrupt politician
DC Apr 1983

Detective Comics #525

Detective Comics #525
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3rd full appearance of Killer Croc
1st full appearance of Jason Todd
Many sources cite Batman #357 as Jason Todd's first full appearance even though his appearance is brief and he is not introduced by name

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