| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| In 1988 this "Material Girl" decided to "Take a Bow" in "Speed-the-Plow" on Broadway | Madonna | $200 | J | BROADWAY BOUND | 2021-04-07 | #8373 | |
| Her 1992 hit "Erotica" sampled "Jungle Boogie" by Kool & the Gang | Madonna | $400 | DJ | THE MUSICAL '90s | 2015-03-30 | #7036 | |
| She won a 1991 Grammy, her first, for best long-form music video for "Blonde Ambition World Tour Live" | Madonna | $400 | DJ | THE MUSICAL '90s | 2007-06-18 | #5256 |