Detective Comics #36 - Professor Hugo Strange (1940) - This comic features the very first appearance of Hugo Strange, pre-dating other Batman rogues such as Joker and Catwoman. This issue is collected in Batman Archives Vol 1 & Batman Chronicles Vol 1.
Batman #1 (1940) - This issue features the second appearance of Hugo Strange and the first appearance of his Monster Men.
Batman: Strange Apparitions (1977) - This comic reintroduces Hugo Strange into the Batman mythos and has Strange discover the Batman's secret identity. Strange creates his Monster Men in this by experimenting on wealthy clients.
Batman Annual #10 (1986) - This comic features possibly the greatest scheme Hugo Strange has ever pulled off. Batman's life is completely destroyed, with Jason Todd being taken away, Alfred suffering a stroke and Bruce being fired from Wayne Enterprises and thrown out of his home. Hugo Strange manages to pull all of this off whilst still believed to be dead.
Batman: Prey (1990/1991) - This comic gives us the best look into Hugo Strange's mind yet and introduces him into the post-crisis DC universe. Strange is made a member of an anti-vigilante task force and is determined to understand the inner working's of Batman's mind. Hugo becomes obsessed with Batman and even starts to dress-up as him in his own apartment. This is an incredibly fascinating look into Strange's mind and is one of his best stories.
Batman: Gotham Knights #8 - Batman: Gotham Knights #11 (2000)- A sequel to Batman: Prey, Transference has Hugo Strange return to Gotham and attempt to reveal Batman's identity to the public. After trying to coax the secret out of Bruce, a fail-safe is activated in Batman's mind which makes him forget he is Batman. Hugo Strange's manipulation and intelligence really shine here.
Batman: Terror (2003) - This interesting comic and sequel to Batman: Prey has Hugo Strange team up with Scarecrow. Although their partnership doesn't exactly go as smoothly as planned...
Batman and the Monster Men (2006) - A retelling of Hugo Strange's classic origin, this comic has Hugo create his Monster Men in order to find a way to change his "physical inferiority". This comic gives a needed revival to Hugo's origin.
I Am Gotham (2016) - This arc features the first appearance of Hugo Strange in the Rebirth continuity and has him use Psycho-Pirate in order to wreak havoc on the city.
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