Delayed response here, as my internet was down for a couple of days...
@1SO - Great analysis! I love the addiction connection. Also agree on comparing both Goodfellas and Godfather to different types of music. I think the seemingly-musical flow of both films is what makes them both so damn rewatchable.
@Oldkid - As I said above, your overall take of just hating all the characters is completely justified. At the end of the day, they're all admittedly pretty awful people...but I've never had problems with their motivations. I saw this film for the first time when I was very (probably too) young...and I've never viewed it as aspirational. I always viewed it as a fascinating and thrilling cautionary tale. It's the first piece of fiction that made me think about systemic, generational causes of crime and violence (as I said in or original discussion, the first time I saw The Wire I felt it was diving deeper into ideas that had first sparked in my mind through Goodfellas.) I feel it completely works in that context.
@Junior - I'm intrigued by your choices of superior gangster movies. I mean Godfather is one of the greatest films of all time, so sure...it's better. And Miller's Crossing is brilliant, but I'd argue is exploring something very different....but are you telling me you find the characters in Scarface or Gangs of New York more sympathetic and compelling? I find both of those films borderline unwatchable (only made it through both because of an admittedly towering performance at the centre of each). I'm curious as to why you find those films superior?
@Chardy999 - I agree. Ambition, enthusiasm and palpable joy that the characters display go a long way in making them interesting.
@Pixote - Thanks for the link! I'm gonna dive into those!