| 100% | BELIEVE | 7 | Cher's comeback, club hit in 1999 |
| 43% | VIDA | 4 | "Livin' la ___ Loca" (Ricky Martin #1 hit in 1999) |
| 42% | COPA | 4 | Club in a Manilow hit |
| 40% | COPA | 4 | Club in a Barry Manilow hit, informally |
| 39% | CHER | 4 | One-named singer with #1 hits in 1965 and 1999 |
| 39% | COPA | 4 | Club in a Barry Manilow hit, with "the" |
| 39% | GERIHALLIWELL | 13 | Singer who had four #1 hits in the UK from 1999 to 2001, including "It's Raining Men": 2 wds. |
| 38% | MAMBO | 5 | Title dance in a 1999 #3 hit |
| 37% | BELIEVE | 7 | Cher's biggest hit |
| 37% | ALICIA | 6 | Cher's portrayer in "Clueless" |
| 37% | TESS | 4 | Cher's role in "Burlesque" |
| 37% | AMBER | 5 | Cher's frenemy in Clueless |
| 37% | TESS | 4 | Cher's character in "Burlesque" |
| 37% | ASIF | 4 | Cher's catchphrase in "Clueless" |
| 36% | HIS | 3 | "The Shoop Shoop Song (It's in ___ Kiss)" (Cher hit) |
| 36% | BELIEVE | 7 | Cher's auto-tuned hit |
| 35% | USHER | 5 | Singer with the #1 hits "Yeah!" and "Love in This Club" |
| 35% | KIARIO | 6 | Korean model hitting the scene in 1999 |
| 35% | BILLSBILLSBILLS | 15 | 1999 Destiny's Child hit |
| 35% | IGOTYOUBABE | 11 | 1960s hit that Cher rerecorded with Beavis and Butt-Head in 1993 |
| 35% | KATICH | 6 | S M —, Australia Test cricketer who hit 125 against India at Sydney in 2004 |
| 35% | WAUGH | 5 | S R —, Australia Test cricketer who hit 102 against England at Sydney in 2003 |
| 35% | CAMILACABELLO | 13 | Pop singer with the hit song "Crying in the Club" (2 wds.) |
| 35% | SANTANA | 7 | Band whose 1999 hit "Maria Maria" is heavily sampled in 18-Across |
| 35% | OMG | 3 | Gryffin and Carly Rae Jepsen's 2019 release that hit #1 on the US Billboard Dance Club Songs chart in November |
| 34% | SONNYBONO | 9 | Cher's former partner in life and music |
| 34% | SISSY | 5 | RuPaul’s 2014 club hit “___ That Walk” |
| 34% | SAYMYNAME | 9 | 1999 hit for Destiny's Child |
| 34% | KIRMANI | 7 | S M H —, India Test cricketer who hit 102 against England in Mumbai in 1984 |
| 34% | LOLA | 4 | In a Kinks hit s/he "walked like a woman and talked like a man" |