Possible Clues:

• Paul of oldies
• ''Put Your Head on My Shoulder'' crooner
• 'I Don't Like to Sleep Alone' singer
• "Put Your Head on My Shoulder" artist Paul
• “Lonely Boy” singer
• Paul who sang ''Having My Baby''
• Paul with 33 Top 40 hits
• Canadian singer with three #1 Billboard hits
• "Put Your Head On My Shoulder" Paul
• Songwriting Paul