The Riddler. Naturally, we all think of the Riddler as a loner (hey, they even

call him that in his DC Encyclopedia entry). After all, his M.O. almost precludes working with other villains. You'll remember that the Riddler seemed a bit out of place in the Legion of Doom, not so much because he was powerless, but because you almost got the feeling he was ratting out his colleagues with his "super-riddles".
But, as is so often the case in life (and certainly in Riddler stories), when we combine this riddling problem with another one, we get a solution. The other problem? The things the Riddler (and any other villian like him) does don't seem very profitable. On his last two outings that I've read, he stole an unsellable ancient manuscript right in front of Batman and beat the snot of Green Arrow. That may be loads of fun (particularly the Green Arrow part), but it don't pay no rent, folks.

The obvious conclusion?
That's not his work; it's his hobby. He (and any other villain whom we usually see stealing "priceless Etruscan snoods" or the like) make their millions in off-camera, less dramatic crime. That's how they buy
giant jigsaw puzzles, super-instant-mesmerizing top hats, and flying fiddle-cars. Like regular people, they go to work, so that they can support themselves and their hobbies.
But isn't being a supervillain a stupid, self-defeating hobby, whose primary results are
batarang scars on the back of your neck, a prison record longer than Plastic Man's arm, and a hefty monthly bill from Paul Gambi? Nope! As Will Pfeiffer hints at in this month's issue of
Catwoman, the "hobby" of supervillaining isn't just fun (and it
is "the most fun you can have with your clothes on", as Catwoman puts it), it's useful because
it gives you street cred. If you've faced a superhero (regardless of the outcome), you earn the respect and fear of everyone else in the criminal community. That kind of cache can't be bought and allows you to muscle in or pull off jobs that an ordinary crook could only dream of.
Is a criminal of even average competence going to be inspired to follow
a badly burned attorney, a fat guy dressed like Uncle Moneybags, or a corny chemist with a skin condition? No. Will they clamor to work for
Two-Face, the Penguin, or the Joker? Yep.
Street cred, folks. The criminals want it and the villains have it, thanks to their "silly and unprofitable" confrontations with heroes.
And people think they're crazy.
The fools, the utter fools!So, why wouldn't the Riddler work with like-minded, smarty-pants villains making millions, so they can all finance their individual confrontation with various heroes? Fraud, identity theft, white collar crime, insider trading, blackmail, cover-ups -- the Riddler-centric gang below would have plenty of work to keep them in the green while they pursue their quizzical hobby of confounding the Forces of Good. And (like the Joker's gang imagined in an earlier post) enough personnel not to fall apart if a couple members happen to be

in jail that week or recovering from heat-vision burns.
The Gamester (who fought the spectacular Sea Devils and needs to become Aquaman's Riddler). Yeah, so what if he probably died in that "Man-Fish" story? No one read it anyway. Give the man some floating gambling casinos and you've got a maritime buddy for the Riddler and another foe for Aquaman (who can always use another "old foe").
The Puzzler (no, not from the Batman TV series; the woman who stymies Superman). She's a redux on the original Golden Age Puzzler who looked, well, very much like the Toyman.

Writers knew how to deal with Superman in the Golden Age; they gave him societal problems and intellectual villains that couldn't be licked by simply throwing a car around (the Puzzler, Mxyzptlk, the Prankster, J. Wilbur Wolfingham, the Ultrahumanite, Lex Luthor). Anyway, perhaps she could be a love interest for one of the others in the group?
Everyone's favorite psychopathic hunchback,
Dr. Riddle (who stumped Bulletman, which I'm sure must be
terribly difficult). Not the smartest member of the bunch, but he's the creepy one you send to scare somebody. Little children, I should think.

The Golden Age villain
Mr. Who, with some toning down of his powers, would fit in and add enormous muscle to the team (with super-strength, regenerative abilities, and chameleon powers). His colleagues could help him use his powers to actually make money instead of just looming over fairgrounds, crushing statues, and fighting Dr. Fate. They could also get him a make-over and a nicer outfit. Yeesh.
The Cluemaster (who's apparently cool now). Our Mr. Brown would have a legitimate function; heroes always look for clues and always find them. Arthur would simply make sure the clues led the wrong way. So what if the Riddler once strapped a bomb to his chest? No one remembers that s

tory now...
The Calculator (you don't think the Secret Society is going to
last, do you?). The Calculator knows all the answers; who else should he work with but the man who knows all the questions? I shudder to think what the Calculator and the Riddler could accomplish if they put their heads together.
The Spellbinder is a traditional Batman villain who relies on disorienting, confusing, and deluding people. She had a rather successful outing against Batman after she got her powers from Neron, but hasn't been seen since. Her brand of mind-games would spice up the gang considerable and be viciously effective under the direction of someone like the Riddler.

Hey, what about
Miss Terry? She's pretty hard up for work since
Mr. E went round the bend. Let's have her turn to crime and act as secretary to this busy little group. Although she'd play a secondary role, in some ways she'd be the smartest one (next to the Riddler) because while they occasionally go to jail, she does not.
Naturally,
Query and Echo will remain. Not only because they are fabulous, but because if the Riddler tried to fire them, they'd beat him up.
And, last but not least,
Quiz Kid (correctly spelled, however). "Real" Robin desperately needs this fun-filled Junior Riddler introduced as a rival in the
Teen Titans, Go! #15. The Riddler would be
great with a kid sidekick!