Tony Bennett, Perry Como, and there’s another guy who’s name I can’t think of, but I know his singing career was financed and started by the mob.
Mussorgsky’s “Boris Godonov” - especially if I’m Russian mafia.
A lot of They Might Be Giants, because I like them, and it would amuse me to hum along to “Birdhouse In Your Soul” on my way to a massive drug buy.
Robert Goulet (but that’s not the guy I was thinking of). Edie Gormet