| 100% | DEMILOVATO | 10 | Singer whose 2009 album "Here We Go Again" hit #1 when she was 16: 2 wds. |
| 54% | MILEYCYRUS | 10 | Singer whose 2008 album "Breakout" hit #1 when she was 15: 2 wds. |
| 45% | BILLIE | 6 | With 31-Across, singer whose 2019 album "When We All Fall Asleep, Where Do We Go?" hit #1 when she was 17 |
| 44% | TRACYCHAPMAN | 12 | Singer whose song "Fast Car," from her self-titled debut album, was a #6 hit in 1988: 2 wds. |
| 40% | BRITNEYSPEARS | 13 | Singer whose "Oops! ... I Did It Again" album went platinum in one week: 2 wds. |
| 37% | PAULSIMON | 9 | Singer whose 1986 hit album 36-Across was named for 28-Across's home (2 wds.) |
| 37% | JUSTINBIEBER | 12 | Singer whose 2015 album "Purpose" yielded three #1 hit singles, including "Sorry": 2 wds. |
| 37% | ROBINTHICKE | 11 | Singer whose 2013 #1 hit "Blurred Lines" was produced by Pharrell Williams: 2 wds. |
| 37% | CELINEDION | 10 | Singer whose 1998 song "My Heart Will Go On" debuted at #1: 2 wds. |
| 37% | BRITNEYSPEARS | 13 | Singer whose hit single "Oops!... I Did It Again" is featured in "& Juliet" (2 wds.) |
| 36% | HARRYSTYLES | 11 | "As It Was" singer whose 2022 album generated four simultaneous top 10 hits: 2 wds. |
| 36% | KELLYCLARKSON | 13 | Singer whose hit single "Since U Been Gone" is featured in the Broadway musical "& Juliet" (2 wds.) |
| 36% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 35% | GWENSTEFANI | 11 | Singer whose 2005 #1 hit "Hollaback Girl" was produced by Pharrell Williams as half of the Neptunes: 2 wds. |
| 35% | PIERCEBROSNAN | 13 | Irish-born actor who costarred in the 2018 movie "Mamma Mia! Here We Go Again": 2 wds. |
| 34% | NORAHJONES | 10 | Singer whose "Feels Like Home" album went platinum in one week: 2 wds. |
| 34% | JLO | 3 | Singer whose "This Is Me ... Now" album dropped in 2024, for short: 2 wds. |
| 34% | JUSTINBIEBER | 12 | Musician whose first album titled "My World 2.0" was declared triple platinum in 2010 when he was just 16 years old: 2 wds. |
| 34% | MARTYROBBINS | 12 | Singer whose "El Paso" was the first "Billboard" #1 hit of the 1960s (2 wds.) |
| 33% | ANDREABOCELLI | 13 | Italian tenor whose 2009 holiday album "My Christmas" was certified double platinum: 2 wds. |
| 33% | AVRILLAVIGNE | 12 | Singer whose 2002 album "Let Go" had three songs top the Mainstream Top 40 chart: 2 wds. |
| 33% | BJTHOMAS | 8 | Singer whose "Raindrops Keep Fallin' on My Head" was the first "Billboard" #1 hit of the 1970s (2 wds.) |
| 32% | DOLLYPARTON | 11 | Country singer whose latest album, "I Believe In You," is geared toward children: 2 wds. |
| 32% | PIERCEBROSNAN | 13 | "Mamma Mia! Here We Go Again" actor who plays Ron Ritchie in "The Thursday Murder Club" (2 wds.) |
| 31% | ADELEADKINS | 11 | British singer whose third studio album fetched her the Album of the Year in the 2017 Grammy Awards : 2 wds. |
| 31% | OTISREDDING | 11 | Singer whose 1968 song "(Sittin' On) The Dock of the Bay" hit #1 posthumously: 2 wds. |
| 31% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 31% | LUKECOMBS | 9 | "Forever After All" country singer whose "The Kind of Love We Make" hit the Billboard Top 10 in 2022: 2 wds. |
| 31% | ELLIEGOULDING | 13 | Singer whose hit single "Love Me Like You Do" is featured in "& Juliet" (2 wds.) |
| 31% | TAYLORSWIFT | 11 | "Anti-Hero" singer whose 2022 album generated ten simultaneous top 10 hits: 2 wds. |