Pop culture did something to men over the past 20 years, something very bad and not at all reversible.
Start with television. If we look at what are, arguably, the two best examples of being a man from television in that time frame we find a sociopathic mob boss from New Jersey and a brilliant ad man doubling as a serial womanizer and functioning alcoholic.
There are very few similarities between Tony Soprano and Don Draper, other than they are both men stuck in the past. Tony is pining for the good old, pre-RICO days his father lived through, a time when men were strong silent types, like Gary Cooper (a description of masculinity Tony made to a female psychiatrist trying to help Tony address his own anger management problems and mommy issues).
Don Draper’s ideals and style are firmly rooted in the 1950’s as the narrative arc of Mad Men races through the 1960’s in six seasons, with Don seemingly the lone holdout for the way things used to be. Even Roger Sterling, his white-haired partner, is dropping acid, going to therapy and growing sideburns while Don sticks to brown liquor, stony silence and hair wax.
Still, if you get past Tony’s tendency to murder loved ones and friends as a matter of convenience, and Don’s massive identity theft that has rendered his whole life a lie, you can see why some men want to, at least secretly, emulate them. Both men have been wrong at least once per season, but neither has ever been accused of being indecisive. Tony struggles to be a good father (one of his biggest character conflicts is trying to toughen up his son while simultaneously protecting him from the violent world of mob rule) and Don has that rare gift of being the very best at what he does, both qualities that many men crave. They dress well, play hard and have those personalities that draw people into their orbit, a certain kind of effortless charm that endears people to them even when they are, for the most part, being massive dicks.
The two men have one other thing that, in my mind, makes them massively likable, or at least likable enough to get us to spend six or seven seasons of Sunday nights with them: neither Jon Hamm as Don Draper or James Gandolfini as Tony Soprano are anything like Ray Romano.