Historical clue formulations

• Britney Spears classic ... or a confession applicable to three answers in this puzzle? — 2023-05-03
• 2000 Britney Spears hit — 2015-10-16
• 2000 Britney Spears hit — 2002-05-03
• 2000 hit album by Britney Spears — 2000-10-17