Yeah, I think it really does depend on what you were exposed to, especially as a kid. Around my house was a ton of jazz instrumentalists, and also vocalists like Sinatra. Tony Bennett, Ella Fitzgerald, etc. Louie Armstrong, definitely, some Billie Holiday, Sarah Vaughn. Then when my brother and I got old enough to buy our own stuff, there was rock and r&b. There was not a single Elvis Presley or Bing Crosby or Dean Martin, and not a single country album. So even now, because I haven't gone out of my way to do so, I know very little of that music. The thing you should know about Sinatra, if you care at all, was that he started as a big band singer, very much in the style of Big Crosby who was the biggest at that time, became a teen idol with the Tommy Dorsey Band, went out on his own (a lot of mythology around how that happened) took a nose dive in the early 50s professionally and personally to the point of multiple suicide attempts, and came back after winning the Academy Award as a much more mature, textured performer who spent his off-time on 52nd Street in New York listening to straight jazz singers like Billie Holiday and Mabel Mercer.
He had taste, and because he was so big he could demand the best from the best musicians and arrangers of the time/ In the early 60s, he started his own record company, Reprise, and that was really his most prolific decade. As in most all cases, it's not the hits, the recognizable tunes where a particular artist stands out. If I have one complaint with his music it's that he didn't do enough small combo stuff. When he did work in a more intimate, as he did with Jobim and also towards the end of his career when he recorded an album with Rod McKuen and even did one or two from Joni Mitchell, I think he did it very well.