Whenever a singer comes on Sirius Jazz and I think to myself, it sounds like Sinatra but I know it's not, the correct guess is usually Matt Monro. Not sure why Monro never really made it big. My guess is that he didn't have as well connected a godfather as Sinatra hadAnd if you’re on a crooner trip at the moment Tang try this album with some background info too.
http://mint-audio-restoration.co.uk/stranger/
View attachment 68444
As an aside, the "crooner" era was something I came to later in life as I cut my teeth like most boomers on classic rock, straight ahead jazz, and of course, classical. For me, the beauty of the "easy-listening" crooners weren't just the songs (with lyrics that meant something and which you could actually understand) but the incredible arrangements for the band. You'll often notice that when Sinatra finishes a song in a live performance, he usually credits the song writer and the arranger either at the beginning or the end. His favorite arranger by far was Nelson Riddle, who he said had more "tricks in his bag" than any other arranger, but he also used Gordon Jenkins and Marty Paich extensively. These things are always personal as I prefer those that could really swing, so if you want to explore this genre, you might consider Sinatra, Sammy Davis Jr. (arguably the greatest entertainer who ever lived although Louis Prima also has claims to that throne), Met Torme, Bobby Darin and Tony Bennett (who everyone knows Sinatra called "the greatest singer" of all). Really beautiful but tamer singers include the one and only Nat King Cole and Dean Martin. That era of great music will sadly never come again although fortunately, much of it is preserved rather well. And no, Harry Connick Jr and Michael Buble (although he's quite enjoyable) do not count!
Finally, and perhaps worthy of a new thread, if I could rent a time machine to go back and hear only 1 concert live, my choice would be Sinatra, Live at the Sands, ini 1966 featuring the Count Basie orchestra and with arrangements by Quincy Jones. That would have been something to see and hear in person.