Historical clue formulations

• Either half of a duo with 14 #1 country hits — 2019-12-21
• Director Apatow — 2016-05-22
• Naomi or Wynonna of country music — 2013-06-03
• "Knocked Up" director Apatow — 2012-05-21
• Filmmaker Apatow — 2010-08-14
• Director Apatow — 2010-07-06
• Film producer Apatow — 2010-02-07
• Actress Ashley — 2000-01-21
• Hirsch of "Taxi" — 1997-10-03