Possible Clues:

• 'Times of Your Life' singer
• Paul of song
• He had a #4 hit with 'It's Time to Cry'
• “The Tonight Show” theme writer
• 'It's Time to Cry' singer, 1959
• 'Put Your Head on My Shoulder' songwriter Paul (whose daughter is married to Jason Bateman)
• "Put Your Head on My Shoulder" songwriter Paul (whose daughter is married to Jason Bateman)
• See 5-Across
• ''Kissin' on the Phone'' singer
• Canada's Walk of Fame inductee, 2005