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I'll be honest, I just think the fact that they both dress like DnD theives is a good aesthetic.
I think the most obvious comparison to Raven is Jean but I think Raven and Magik going to hell to face their demon's would be cool.
I'm an unapologetic fan of grown up Tim in this Red Robin costume. Panel from Teen Titans 2003 #93 with art by Nicola Scott.
The Fab Five all grown up from JLA/Titans #3. Art by Phil Jimenez.
@NottheWolf Possibly. They've been progressively uping the range of what he can turn into over the years. He could theoretically just turn into that exact dragon for all I know.
So this has been bugging me nonstop but where did Kon get the new outfit when he arrived on Gemworld with no bags? They even bring up it was made on Earth.