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I'm convinced that The Riddler would love running a D&D campaign for the other rogues. It would be a great way for him to challenge them with fun puzzles, and Eddie being Eddie, he'd be sure to come up with some mind-bending lore with an insane twist that absolutely NO ONE would see coming. He'd be having the time of his life, he'd prep for his sessions weeks in advance (and the party would probably be stuck on his puzzles for days, but they'd all humor him anyway).

Penguin would play a wizard - I think the other rogues suggested warlock for him when he was building his character, but he refused - he's gained enough power from shady deals in real life; he wants a character who doesn't rely on anyone else to get power.

Scarecrow would be the warlock - I think he likes the idea of having a dark deity who he works with to change the world - I think that's how he sees fear, in a way.

Two-Face would play a paladin - someone with a divine, noble quest (just like Harvey's own divine quest for justice in Gotham).

Harley Quinn would play a barbarian - I think playing a character who's loud, tough, and likes to hit things with a big stick would appeal to her.

I think they would be the main party, but the other rogues might participate in individual sessions here and there.

Mr. Freeze would play a cleric - d&d would be his form of therapy in that way - he can't heal Nora in real life, but he can heal everyone in the party.

Catwoman would play a rogue - stealing is just too much fun for her to consider playing anything else.

Bane would play a fighter - someone who just has one or two attacks that he doesn't have to think about too much.

Joker would play a bard, of course, because he always needs to be the center of attention.

Ok, so I have a fan theory / headcanon about Riddler from the Batman Arkham games - I think that at some point between Arkham City and Arkham Knight, he became a dad. Here is my evidence, in order from least to most convincing (some minor spoilers included):

Riddler makes several references to children’s games, songs, and fables when Batman is completing the racing challenges (the wheels on the bus, the tortoise and the hare, and even Mario Kart - “don’t tell me I have to hover in front of you with a flag to get you to turn around!”)

In an effort to get Batman to focus on rescuing Catwoman, Riddler at one point promises him a banana if he goes to the next location - bribery is a very common tool used by new parents to get their kids to cooperate

Throughout the storyline involving Catwoman, Riddler is constantly forcing the two to work together (almost like he has experience dealing with small children who don’t always get along). At one point he actually refers to Batman and Catwoman as children

There is green graffiti all over Gotham, much of it splotchy like it was rushed - or like there was child participation. I’m also pretty sure I saw a few handprints, which, I mean, come on...

Several of Riddler's puzzles in Arkham Knight were familiar puzzle games - the kind you might see in a toy shop or at a carnival. Why would Ed have suddenly stopped coming up with his own puzzles? Maybe because he’s very busy entertaining a small child at home (or maybe these puzzles were some of the favorites of his little one)

His death robot at the end of the game looks an awful lot like Mr. Electric from Sharkboy & Lavagirl - could it be possible that he watched it with his child and took inspiration from there?

In the movie studios, he plays “Riddler Says” with Batman - another popular children’s game

He has now taken the time to make sure all of his riddles rhyme, so that they now sound like nursery rhymes - could it be that this was his child’s idea?

At the beginning of his side quest, he lays out a clear list of rules for Batman - just like the rules you would tell a child before babysitting them

Particularly, rules 7 and 8 - if you need to use the bathroom, you must hold it, and if you have an accident, it is not my fault - if that’s not an exhausted dad who’s had to deal with said accidents far too often, I don’t know what is

And finally, and most obviously, the Riddler’s choice of clothes in Arkham Knight is very reminiscent of a suburban dad - the Hawaiian shirt is a dead giveaway

The human heart isn’t dead center, it’s slightly to the left, right?