Historical clue formulations

• Comic who sang "I Love to Laugh" in "Mary Poppins" — 2013-03-19
• "The Diary of Anne Frank" Oscar nominee — 2011-02-26
• Player of the Texaco Fire Chief, on old radio — 2004-02-13
• Radio comedian dubbed "The Perfect Fool" — 2001-10-20
• The Perfect Fool — 2000-07-20