| 100% | JENNIFERLOPEZ | 13 | "I'm Real" singer who became a mother of twins in 2008: 2 wds. |
| 75% | MARIAHCAREY | 11 | "We Belong Together" singer who became a mother of twins in 2011: 2 wds. |
| 70% | RICKYMARTIN | 11 | "Livin' la Vida Loca" singer who became a father of twins in 2008: 2 wds. |
| 48% | JOHNLEGEND | 10 | "All of Me" singer who wrote a song in "SpongeBob SquarePants: The Broadway Musical": 2 wds. |
| 47% | TROPICTHUNDER | 13 | 2008 movie about a group of actors who fight in a real-life war: 2 wds. |
| 46% | BRITNEYSPEARS | 13 | Singer who appears nude in the video of her 2008 single, "Womanizer": 2 wds. |
| 45% | EDSHEERAN | 9 | British singer who made a cameo in HBO series "Game of Thrones: 2 wds. |
| 45% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 44% | BILLIEEILISH | 12 | Singer who released "Birds of a Feather" in 2024: 2 wds. |
| 43% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 43% | ANNEMURRAY | 10 | "You Needed Me" singer who was made a Companion of the Order of Canada in 1984: 2 wds. |
| 43% | NELLYFURTADO | 12 | Singer who released "I'm Like a Bird" in 2000: 2 wds. |
| 42% | JOHNLEGEND | 10 | "All of Me" singer who competed against Alicia Keys in a 2020 episode of "Verzuz": 2 wds. |
| 42% | MICHAELSTIPE | 12 | Singer who came up with "It's the End of the World as We Know It (And I Feel Fine)" in his sleep: 2 wds. |
| 41% | DIANEKEATON | 11 | Actress who plays a mother in "Father of the Bride" (2 wds.) |
| 41% | ALANCUMMING | 11 | Scottish-born actor on "The Good Wife" who became a US citizen in 2008: 2 wds. |
| 41% | SMOKEYROBINSON | 14 | Singer who performed "U Really Got a Hold on Me" (a parody of "You've Really Got a Hold on Me") on "Sesame Street": 2 wds. |
| 41% | JLO | 3 | Singer who's a "World of Dance" judge, for short: 2 wds. |
| 40% | JOHNLEGEND | 10 | "All of Me" R&B singer who sold his music catalog in 2022: 2 wds. |
| 40% | CELINEDION | 10 | "The Power of Love" singer who was made a Companion of the Order of Canada in 2008: 2 wds. |
| 40% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 39% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 39% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 39% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 39% | JONIMITCHELL | 12 | "Big Yellow Taxi" singer who was made a Companion of the Order of Canada in 2002: 2 wds. |
| 39% | ERYKAHBADU | 10 | "Tyrone" singer who competed against Jill Scott in a 2020 episode of "Verzuz": 2 wds. |
| 39% | MILEYCYRUS | 10 | Singer who appears nude in the video of her 2013 single, "Wrecking Ball": 2 wds. |
| 39% | LUCYDACUS | 9 | "Kissing Lessons" singer who is also a member of 16-Across: 2 wds. |
| 38% | LIAMPAYNE | 9 | One Direction singer who has a fear of spoons: 2 wds. |
| 38% | GARYOLDMAN | 10 | "Darkest Hour" actor who voices a Russian sergeant in 2008's "Call of Duty: World at War": 2 wds. |