I never give titles.

Who wants to read comic books from 60 years ago ! As an aspiring Riddler fan you do!

Detective comics: #140 ,# 142, #362, #364, #377 Batman: #171 , #179 , #263 , #279, #317 The Brave and the Bold : #183

The Dark Knight, Dark City is a must-read. It was the first attempt at making him into a 'serious villain,' thus bringing him in line with the darkening tone of Batman comics at the time. (Originally Batman: #453, #454, #456)

The quintessential origin story (We do not have another one you see) Detective comics Annual #8

Batman Confidential #26-#28. This is my favourite Riddler story.

A few gems from the '90s (we used to have good standalone Riddler stories, and some very bad ones) Run, Riddler Run, The Riddle Factory, and Batman Chronicles #3 Not so Honorable mention : Legends of the Dark Knight (#109, #110, #111) We never learn what was the "primal riddle". That time when a teenager made a fool out of him: Impulse Vol. 1 #48

All the BTAS and TNBA tie in comic appearances:

Batman Adventures vol. 1 : #10 Batman Adventures vol. 2: #2, #11 The Batman and Robin Adventures vol. 1 : #3, #21 Batman: Gotham Adventures : #11, #28, #56, #57

The Chuck Dixon bargain bin:

Robin: #63, #64 ,#65 Detective Comics: #705, #706,#707

When He was a Private Dick.

Detective Comics: #822, #824, #828, #837, #845 Gotham City Sirens: #3, #9, #10 Batman 80-Page Giant, the second story (2010) Honorable mention: Trinity (2008) , Joker's Asylum II : The Riddler, (I excluded the stories where he reverts back to villainy . These are only required if you are embarking on a quest for your advanced degree in Riddlerology)

Assorted stories pre New 52: Detective Comics #797 , #798, 799 Legends of the Dark Knight #185, #186, #187, #188, #189 (This is his 'hot topic,' metrosexual era. After Hush, they really didn't know what to do with him. These stories aren't good, but I am attached to them like you are to an elderly dog that has only three days left to live.) Green Arrow: The City Walls story line Vol #34-#50 (He appears in more prominently in #35,#36,#37)

The new 52, and post Rebirth medley : Batman (2011): Zero Year. (Batman #21 -#33) Read and cherish it, because after this we are entering the Riddler flop era. I do not take responsibility for the quality and merit of the following issues. Some of these are actually okay; good luck dumpster diving.

Batman: #23.2 Detective Comics: Future Ends The Riddler : Year of the villain Detective comics : #1060, #1061 (two reasons why he should always be clean shaven) Batman Black and White Vol. 2 #5 Batman Urban Legends: #17 (The second short story) Strange Love Adventures: Diner For Two Legends of the Dark Knight Vol. 2 : #4, #5 The Audio Adventures Special Vol. 1 (What burns when it's green) The Joker Presents: A Puzzlebox. Batman / Faze clan (Makes you wonder how much a promotional comic book four your business would cost.) Honorable mention to the Batman 2022 Year One Comic book

The Tom King Special (Proceed with caution)

The War of Jokes and Riddles: Batman #25-#32 Batman: One Bad day :The Riddler Killing time

To cleanse your palate read Batman #3 , from Fraction's current Batman run.

Is this list exhaustive? Oh my god, no. I mostly skipped over appearances he had in various events like Knightfall, No Man's Land, and 'Their Dark Designs' , as well as his numerous appearances in Jeph Loeb's writing, such as 'When in Rome ' and 'Hush', and whatever Eddie was up to in Chip Zdarsky's run. There are also many more comic book issues where he only graces the pages with his presence briefly, without being the focus of the story. You could, for example, pick up Catwoman: Lonely City by Cliff Chiang, where he plays a minor but interesting part, not to mention his recent appearances in the ongoing Absolute Batman series.