What about popular culture? Are there movies today that portray criminals as sympathetic characters? The heist film — The Town, Fast Five, Oceans 11, or Inception — remains alive. But the heists in contemporary films are so complicated, require so much planning, training, and teamwork to pull off, that they send the message that you might as well become a second unit movie director. A lot of heist movies these days are actually metaphors about making movies — Inception, most obviously — and movies these days are ridiculously complicated to make.
Moreover, movies promote themselves with "The Making of" documentaries about how complicated they are to make. How many young people have watched The Making of Inception documentary about how many hundreds of experts had to work together to make a movie about expert criminals?
It must be quite daunting for young would-be criminals to be told over and over again by their favorite movies that only by organizing superbly can they become successful criminals.
It's like the flip side of the CIS crime shows on TV that have taught a generation that cops have giant computer monitors that will instantly display the faintest clue that will prove the perp guilty. Heist movies teach the lesson that if you want to outsmart all that CIS technology, you'd better belong to a gang of genius criminals, each of whom is the master of some arcane field of knowhow.
I can imagine that a lot of 13-year-olds would think it cool to join a gang like that, but they don't know any gangs like that. They look around at the gang members they know, like their cousin Jesus, and most of them seem like doomed idiots.
My impression is that popular culture today has gotten rather authoritarian or militaristic. Cops used to be portrayed as big dumb Irishmen, easy to outwit. But now, they're portrayed as practically Seal Team 6, with lots of cool weapons and training. Authority has most of the glamor these days, while criminals seem like losers.