That's pretty interesting. I think i'd go for a different slant on it though - I'd have Bruce Wayne as the Ultimate (No Pun Intended) Thrill seeker. Theres nothing in his rich pampered life that actually gets him going anymore, so he does this because it's the only thing that'll give him a thrill. He goes out at Night, dressed as a lunatic and beats the crap out of Villains.
Eventually, he'd loose his family that'd strengthen his resolve. I'd probably have his costume more like Midnighters as well, ditch the cape and the belts, and make it more along the lines of A long black trench coat, with a "Ultimate Adventures" style face mask. Big eyes that're goggles, and a leather look to cover him. He'd have Captain America style pockets and pouches over him as well.
I'm not sure if i'd bring Robin, or Nightwing into it, but it seems like a perfect opportunity to start like a little "club." Something along the lines of these characters all seeking thrills and then deciding to do something a bit more...conventional.
What about Ultimate Superman? How would THAT one go down?
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