Historical clue formulations

• 1990 #1 rap hit that ends "too cold, too cold" — 2022-07-20
• 1990 #1 hit that begins "Yo, V.I.P., let's kick it!" — 2021-04-27
• First hip-hop single to top the Billboard Hot 100 (1990) — 2019-04-26
• 1990 hit that samples the bass line from Queen/Bowie's "Under Pressure" — 2016-10-31
• 1990 #1 hit that starts "Yo, V.I.P., let's kick it!" — 2015-11-14
• 1990 #1 rap hit that starts "Yo, V.I.P., let's kick it" — 2008-02-29
• 1990 #1 rap hit — 2006-08-11
• 1990 Vanilla Ice hit — 1999-10-13