Chuck Berry
Buddy Holly
Chet Baker
Chet Baker. Before the heroin ravaged him and he got his teeth knocked out, he was so handsome.
That, plus the singing voice and his playing. He was obviously very influenced by Miles Davis, and only had a fraction of his talent, but only being a quarter as talented as Miles Davis still makes you one of the greatest trumpet players of all time.
Chet kinda had that perfect balance of classically rugged and masculine qualities while also having soft, delicate, effeminate and pretty features at the same time.