| # | Clue | Answer As Given | Value | Round | Category | Air Date | Show |
|---|---|---|---|---|---|---|---|
| His "Don't Be Cruel"(& it's not Elvis) | Bobby Brown | $1,200 | DJ | THEIR '80s NO. 1 ALBUM | 2022-12-02 | #8755 | |
| His second album contained 3 "cruel" songs: "Cruel Prelude", "Don't Be Cruel" & "Cruel Reprise" | Bobby Brown | $1,000 | J | ALBUMS | 2003-11-24 | #4421 | |
| He left New Edition, going solo with hits like "Don't Be Cruel" & "Every Little Step" | Bobby Brown | $100 | J | POP & ROCK MUSIC | 1993-05-14 | #2015 |