Historical clue formulations

• Title role in the Best Picture of 1962 — 2023-05-30
• With 40-Down, film that opened on 12/16/1962 — 2012-12-12
• Obama economic adviser Summers — 2010-02-21
• Jack who wrote the lyrics to "Tenderly" — 2008-06-29
• Lyricist Jack — 1997-04-08