No. 02: Vanilla Ice, Ice Ice, Maybe

Wed, 21 Oct 2026 09:00:00 +0000

He had the first rap single ever to top the Billboard Hot 100. Thirty-three years later, he was the entertainment at a pro soccer team’s ’90s night in Houston.

Then (1990): The first rap single to top the Billboard Hot 100
Now (2023): The entertainment at a pro soccer team’s ’90s night

Source: Stereogum

Fade-o-Meter: 6/10 (Nostalgia tour). Satire and commentary.

No. 01: Taylor Hicks, Do I Make You Proud?

Wed, 14 Oct 2026 09:00:00 +0000

He won American Idol after 63.4 million votes were cast. Less than two years later his label had dropped him, and before long he was hosting a show about state foods on INSP.

Then (2006): Winner of American Idol, with 63.4 million votes cast on the night
Now (2023): Host of State Plate, a show about each state’s signature foods, on INSP

Source: Guinness World Records

Fade-o-Meter: 8/10 (State-food TV host). Satire and commentary.

Has-Been of the Year

No. 02: Vanilla Ice, Ice Ice, Maybe

No. 01: Taylor Hicks, Do I Make You Proud?