| 100% | RICKYMARTIN | 11 | "Livin' la Vida Loca" singer who became a father of twins in 2008: 2 wds. |
| 65% | JENNIFERLOPEZ | 13 | "I'm Real" singer who became a mother of twins in 2008: 2 wds. |
| 57% | MARIAHCAREY | 11 | "We Belong Together" singer who became a mother of twins in 2011: 2 wds. |
| 54% | RICKYMARTIN | 11 | "Livin' la Vida Loca" singer who records in both English and Spanish: 2 wds. |
| 42% | BRITNEYSPEARS | 13 | Singer who appears nude in the video of her 2008 single, "Womanizer": 2 wds. |
| 41% | CHRISMARTIN | 11 | Coldplay lead singer who sang "Viva La Vida" in "Carpool Karaoke": 2 wds. |
| 41% | RICKYMARTIN | 11 | Singer whose song "Livin' La Vida Loca" peaked at number one on the Billboard Hot 100 chart in 1999: 2 wds. |
| 40% | EDSHEERAN | 9 | British singer who made a cameo in HBO series "Game of Thrones: 2 wds. |
| 40% | BILLIEEILISH | 12 | Singer who released "Birds of a Feather" in 2024: 2 wds. |
| 40% | RICKYMARTIN | 11 | Puerto Rican singer of the 1999 hit "Livin' la Vida Loca": 2 wds. |
| 40% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 38% | ALANCUMMING | 11 | Scottish-born actor on "The Good Wife" who became a US citizen in 2008: 2 wds. |
| 38% | JOHNLEGEND | 10 | "All of Me" singer who wrote a song in "SpongeBob SquarePants: The Broadway Musical": 2 wds. |
| 37% | TROPICTHUNDER | 13 | 2008 movie about a group of actors who fight in a real-life war: 2 wds. |
| 37% | JLO | 3 | Singer who's a "World of Dance" judge, for short: 2 wds. |
| 37% | CELINEDION | 10 | "The Power of Love" singer who was made a Companion of the Order of Canada in 2008: 2 wds. |
| 36% | RICKY | 5 | ___ Martin, "Livin' La Vida Loca" singer who was born on Christmas Eve |
| 36% | ERYKAHBADU | 10 | "Tyrone" singer who competed against Jill Scott in a 2020 episode of "Verzuz": 2 wds. |
| 36% | MILEYCYRUS | 10 | Singer who appears nude in the video of her 2013 single, "Wrecking Ball": 2 wds. |
| 36% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 35% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 35% | ANNEMURRAY | 10 | "You Needed Me" singer who was made a Companion of the Order of Canada in 1984: 2 wds. |
| 35% | JONIMITCHELL | 12 | "Big Yellow Taxi" singer who was made a Companion of the Order of Canada in 2002: 2 wds. |
| 35% | JLO | 3 | Nickname for the female singer who became an "American Idol" judge in 2011: 2 wds. |
| 35% | MIRANDALAMBERT | 14 | "Vice" singer who came in third on the first season of "Nashville Star": 2 wds. |
| 35% | PAULMCCARTNEY | 13 | 76-year-old singer who is still in a "Band on the Run": 2 wds. |
| 35% | BRIANWILSON | 11 | Pop singer who's the father of singers Wendy and Carnie: 2 wds. |
| 35% | LUCYDACUS | 9 | "Kissing Lessons" singer who is also a member of 16-Across: 2 wds. |
| 35% | LIAMPAYNE | 9 | One Direction singer who has a fear of spoons: 2 wds. |
| 35% | GARYOLDMAN | 10 | "Darkest Hour" actor who voices a Russian sergeant in 2008's "Call of Duty: World at War": 2 wds. |