Historical clue formulations

• Sinatra portrayer on "S.N.L." — 2011-01-09
• Sinatra impersonator on "S.N.L." — 2007-03-25
• Early 80's "S.N.L." comic — 2003-02-21
• Former "S.N.L." comic — 1998-12-20
• Onetime Sinatra impersonator — 1998-06-12