Possible Clues:

• 'Put Your Head on My Shoulder' singer Paul
• Artist with the 2013 album ''Dianacally Yours''
• He hit #1 in '59 just before Presley
• 'Annette Sings ___' (1960 pop album)
• Paul from the '60s
• "Puppy Love" crooner Paul
• '(You're) Having My Baby' singer
• 'Put Your Head on My Shoulder' songwriter
• 50's-60's teen idol