Tom Jones is cheesy but fascinating- he's not someone like Bobby Darin who sits on the border of rock and classic pop with one foot in both sides. He's a rock singer who happens to sing mostly classic pop and jazz material. As he's gotten older, he's actually returned more and more to his roots in rock, blues, gospel and R&B, which is the opposite of other singers in his generation, who do American Songbook once they're too old to rock like they used to.
His recordings of "Send In The Clowns" and "The Impossible Dream" are wonderful in the same slightly high-camp way. On an unrelated note, I often wish Freddie Mercury had lived long enough to do a Songbook album.
This brings up a point I have been meaning to bring up: if a production of Evita starred a male performer as Eva,what would you think? I think it would work if the performer was good enough, and the audience let their guard down. However, if the audience was against the idea, then the most talented performer could not succeed. What do you think an audience would do, as of today?
"Sticks and stones, sister. Here, have a Valium." - Patti LuPone, a Memoir