Did they carry the same seemingly universal reputation for old school coolness they have among legions of dads over the past few decades, or was mainstream society more mixed about them? Were they considered too raunchy or dissolute?
Well, there's this...
Vanity Fair (among other magazines) has retold the story about Frank Sinatra's problems with The Godfather. You remember that scene with the horse's head, right? The guy in the bed is a movie producer who didn't want to cast a certain musician in one of his movies.
The musician was fictional, but his character seemed pretty close to a couple high-profile entertainers of the time... especially Frank Sinatra, who kind of took it personally:
Along with Joe Colombo and the Mob, the producers also had to contend with Frank Sinatra during pre-production. Sinatra despised The Godfather, both as a book and as a movie, and for good reason: the character of Johnny Fontane, the drunken, whoring Mob-owned singer turned movie star who enters Puzo’s novel on page 11, sloppy drunk and fantasizing about murdering his “trampy wife when she got home,” was widely believed to have been based on Sinatra. In his desire to rise from singer to actor, Fontane also seemed to resemble Al Martino, who had performed in gangland nightclubs on both coasts and in Vegas. Phyllis McGuire, one of a famous singing-sisters trio and the girlfriend of mobster Sam Giancana, thought Fontane was a dead ringer for Martino....
Meanwhile, at Chasen’s restaurant in Los Angeles one night in 1970, Mount Sinatra erupted. The singer was seated at a banquette with his friend Jilly Rizzo when Ruddy walked in with Puzo. Like many other Italian-Americans, Puzo had grown up with two pictures on a wall in his family’s house—the Pope’s and Frank Sinatra’s. “I’m going to ask Frank for his autograph,” he said.
“Forget it, Mario. He’s suing to stop the movie,” said Ruddy.
But when Ruddy started table-hopping, a Hollywood climber, hoping to impress Sinatra, grabbed Puzo and steered him to the singer’s table. Sinatra turned purple with rage. “I ought to break your legs,” he fumed at the writer. “Did the F.B.I. help you with your book?”
“Frank is freaking out, screaming at Mario,” Ruddy recalls. Puzo later wrote that Sinatra called him “a pimp” and threatened “to beat the hell out of me.”
So I'm not saying Sinatra and the rest of the Vegas crowd were connected, if you know what I'm saying.
But it's pretty undeniable that some people thought they were.
Beyond that, I know I've read things that painted crooners like Sinatra and Dean Martin as kind of effete, with an undercurrent of suspicion about their origins. I believe the whole Rat Pack were either Catholic or Jewish - Peter Lawford, I'm not sure about, but he had a family connection to the Kennedys, so....
That, I'd find it harder to source. A lot of it is kind of between the lines, and the Rat Pack singers were kind of a second wave of crooners after Rudy Vallee and Bing Crosby, and were more apt to kind of poke fun at themselves and defuse critical attitudes with satire. (Like, I haven't read Real Men Don't Sing, but I'm pretty sure it's focused on the earlier radio stars, and not the stuff that rose to prominence in the mid-40s to early 50s.)
In England, the BBC did announce a "crooner ban" in 1942, because sentimentality was seen as damaging to the war effort. It made news in Chicago at the time. The official announcement read, in part:
"…it has learned beyond all doubt that the 1942 public as a whole finds the sempiternal sob of the crooner almost as distasteful and distressing as, say, flippant blasphemy or an indecent innuendo. At the end of the third year of an increasingly strenuous war the public is demanding something more virile, more robust."
A few of Sinatra's songs were banned specifically for a variety of reasons, including blasphemy ("Light A Candle In Church", 1942) and innuendo ("How Little We Know", 1956)... so for at least some British censors, no, he wasn't "cool" at all.