I don’t think Black Mass has been mentioned. Not top 5 but fun to watch Depp chew the scenery as Whitey Bulger. I think part of the problem is the definition of gangster. When I hear gangster movies, I’m thinking the mafia, or at least established organized crime. Some of my all time favorite moves, like Heat and Ronin, are great crime movies but not gangster movies. And I think Untouchables depends somewhat on your age. I was 15 when it came out in 1987 and I saw it in the theater. It was a huge role for Costner coming off of a great supporting part in Silverado (great fucking movie) and the start of a run that would include No Way Out, Bull Durham, Field of Dreams, Dances With Wolves, and Robin Hood in the next *four years*. Connery was in great form and already a legend, but he was coming off of Highlander and The Name of the Rose, not exactly blockbusters, so it was exciting to see him in such a good role for him. Deniro was on his way to being a legend but was coming off some odd roles too, like The Mission and Angel Heart, and this put him right back on track for legend. I had never seen anything like the baseball bat scene. Point is that if you are Gen X there is a lot of nostalgia around Untouchables, and as an 80s movie (there was a LOT of crap in the 80s) I think it holds up well.