Frank Sinatra
It is pretty uncontroversial that Frank has Dean beat on singing alone. But he can take him in movies too. Sinatra’s movies, especially those alongside Gene Kelly including the Oscar-winning Anchors Aweigh (1945) were major critical and public successes.
Dean Martin
Dean Martin can sing, act and make people laugh. He’s an all-round entertainer. Sinatra is the better singer, for sure, and maybe made some better movies. Martin’s work with Jerry Lewis is beloved by millions. And the Golden Globe winning The Dean Martin Show ran for 264 episodes. The question is who is the better entertainer and on this, Dean has Frank beat.
Sinatra is credited by some music historians with creating the first concept album. His 1946 album, The Voice of Frank Sinatra, featured eight tracks all on the same theme. It was Frank’s first album and cost $2.50 which is a hefty $37.00 in today’s money. Although Frank was considered a teen idol and popular with female fans, this popularity might have had something to do with the reported $5 some would be paid by Sinatra’s management to keep screaming throughout his shows. Sinatra was, infamously, a massive Sinatra fan but he didn’t love all his songs. My Way and Strangers in the Night were loathed by the ‘Chairman of the Board’. Oh, and he hated being called that.