| 100% | MICHAELBOLTON | 13 | Singer whose "Big, Sexy Valentine's Day Special" premiered on Netflix in 2017 (2 wds.) |
| 38% | PAULMCCARTNEY | 13 | Singer whose character shrank in 1965's "Help!": 2 wds. |
| 37% | BRETTELDREDGE | 13 | Country singer whose "Baby, It's Cold Outside" topped the Adult Contemporary chart in 2017: 2 wds. |
| 36% | ADELEADKINS | 11 | British singer whose third studio album fetched her the Album of the Year in the 2017 Grammy Awards : 2 wds. |
| 36% | SEXY | 4 | "Michael Bolton's Big, ___ Valentine's Day Special" (2017 Netflix show) |
| 36% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 36% | VASCOROSSI | 10 | Italian singer whose Enzo Ferrari Park concert in 2017 is the highest-attended ticketed concert for a single artist: 2 wds. |
| 36% | THOMASRHETT | 11 | Country singer whose album "Life Changes" topped the Billboard 200 in 2017: 2 wds. |
| 34% | NIAVARDALOS | 11 | "I Hate Valentine's Day" actress who plays Toula Portokalos in, and wrote and directed, "My Big Fat Greek Wedding 3" (2 wds.) |
| 33% | FAITHHILL | 9 | Country singer whose song "Breathe" was named the #1 single on Billboard's year-end countdown in 2000 (2 wds.) |
| 33% | PETESEEGER | 10 | Folk singer whose anti-Vietnam War song on 15-/51-Across's show was censored by CBS: 2 wds. |
| 33% | KUMAILNANJIANI | 14 | "Silicon Valley" actor who starred as a semifictional version of himself in 2017's "The Big Sick": 2 wds. |
| 33% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 33% | THEWEEKND | 9 | Canadian singer whose "Blinding Lights" was the #1 song on Spotify in 2020: 2 wds. |
| 33% | BRITNEYSPEARS | 13 | Singer whose "Oops! ... I Did It Again" album went platinum in one week: 2 wds. |
| 33% | BOBDYLAN | 8 | "Blowin' in the Wind" singer whose image appears on the cover of the Beatles' "Sgt. Pepper's Lonely Hearts Club Band" album: 2 wds. |
| 33% | NORAHJONES | 10 | Singer whose "Feels Like Home" album went platinum in one week: 2 wds. |
| 33% | SELENAGOMEZ | 11 | "Come & Get It" singer whose first TV series lead role was on Disney's "Wizards of Waverly Place": 2 wds. |
| 33% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 33% | JLO | 3 | Singer whose "This Is Me ... Now" album dropped in 2024, for short: 2 wds. |
| 33% | MILEYCYRUS | 10 | "Party in the U.S.A." singer whose first TV series lead role was on Disney's "Hannah Montana": 2 wds. |
| 33% | DEMILOVATO | 10 | "Heart Attack" singer whose first TV series lead role was on the Disney Channel's "Sonny with a Chance": 2 wds. |
| 32% | DOLLYPARTON | 11 | Country singer whose latest album, "I Believe In You," is geared toward children: 2 wds. |
| 32% | KENNETHBRANAGH | 14 | Actor who played Hercule Poirot in 2017's "Murder on the Orient Express" and 2022's "Death on the Nile": 2 wds. |
| 32% | AMERICANGODS | 12 | A 2017 TV series that premiered on Starz, in which Gillian Anderson plays the new goddess Media: 2 wds. |
| 32% | OTISREDDING | 11 | Singer whose 1968 song "(Sittin' On) The Dock of the Bay" hit #1 posthumously: 2 wds. |
| 32% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 31% | KELLYCLARKSON | 13 | Singer whose debut single "A Moment Like This" reached #1 on the Billboard Hot 100 in 2002: 2 wds. |
| 31% | MEGHANTRAINOR | 13 | Singer whose debut single "All About That Bass" reached #1 on the Billboard Hot 100 in 2014: 2 wds. |
| 31% | COBRAKAI | 8 | "The Karate Kid" sequel series on Netflix with a venomous snake in the title: 2 wds. |