The best male singers of the 20th century can be categorized into eras. First there was Al Jolson, followed by Bing Crosby, than came Frank Sinatra, and than Elvis Presley. I don't know if I can include anyone after Elvis as being in contention for top male vocalist for the century, even though there were some great male singers. Out of the above mentioned singers, I would select Bing Crosby as the top male vocalist. I think he had the best singing voice of them all. Al Jolson would be second, Sinatra third, and than Elvis.