| 100% | OTISREDDING | 11 | Singer whose 1968 song "(Sittin' On) The Dock of the Bay" hit #1 posthumously: 2 wds. |
| 51% | TRACEADKINS | 11 | Singer whose "Ladies Love Country Boys" hit #1 on the Billboard Country Songs Chart in 2007: 2 wds. |
| 51% | ALANJACKSON | 11 | Singer whose "Country Boy" hit #1 on the Billboard Hot Country Songs Chart in 2009: 2 wds. |
| 50% | BRANDICARLILE | 13 | Singer whose 2021 hit song "Right on Time" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 50% | BJTHOMAS | 8 | Singer whose "Raindrops Keep Fallin' on My Head" was the first "Billboard" #1 hit of the 1970s (2 wds.) |
| 48% | JANISJOPLIN | 11 | Singer whose 1971 song "Me and Bobby McGee" hit #1 posthumously: 2 wds. |
| 48% | KELLYCLARKSON | 13 | Singer of the 2015 hit "Heartbeat Song": 2 wds. |
| 48% | RACHELPLATTEN | 13 | Singer of the 2015 hit "Fight Song": 2 wds. |
| 48% | SARABAREILLES | 13 | Singer of the 2007 hit "Love Song": 2 wds. |
| 48% | REDDING | 7 | "(Sittin' On) The Dock of the Bay" singer |
| 48% | OTISREDDING | 11 | "(Sittin' On) The Dock of the Bay" singer |
| 47% | OTIS | 4 | "(Sittin' On) The Dock of the Bay" singer Redding |
| 47% | OTIS | 4 | “(Sittin’ On) The Dock of the Bay” singer Redding |
| 47% | THEWEEKND | 9 | Canadian singer whose "Blinding Lights" was the #1 song on Spotify in 2020: 2 wds. |
| 47% | OTIS | 4 | “(Sittin’ On) The Dock of the Bay” singer-songwriter Redding |
| 47% | OTIS | 4 | ___ Redding, "(Sittin' On) The Dock of the Bay" singer |
| 46% | OTISREDDING | 11 | US singer-songwriter whose posthumous album The Dock of the Bay was released in 1968 |
| 46% | DAVIDCOOK | 9 | Singer of the 2008 song "Light On": 2 wds. |
| 45% | RESERVOIRDOGS | 13 | 1992 Quentin Tarantino film whose soundtrack features a cover version of the 1968 hit song "Magic Carpet Ride" (2 wds.) |
| 44% | OTIS | 4 | Redding who was Sittin' On the Dock of the Bay |
| 44% | GWENSTEFANI | 11 | Singer whose 2005 #1 hit "Hollaback Girl" was produced by Pharrell Williams as half of the Neptunes: 2 wds. |
| 44% | OTIS | 4 | "Sitting on the dock of the Bay" singer |
| 44% | MARTYROBBINS | 12 | Singer whose "El Paso" was the first "Billboard" #1 hit of the 1960s (2 wds.) |
| 44% | RODSTEWART | 10 | Singer of the 1971 #1 hit song "Maggie Mae" (2 wds.) |
| 44% | LONELYBOY | 9 | Hit song by Paul Anka which was also used as the title of the documentary made on him: 2 wds. |
| 43% | ISAACHAYES | 10 | Singer of the 1971 #1 hit song "Theme from Shaft" (2 wds.) |
| 43% | THEOSMONDS | 10 | Singers of the 1971 #1 hit song "One Bad Apple" (2 wds.) |
| 43% | LUKECOMBS | 9 | Singer whose 2023 hit "Fast Car" spent 8 weeks at #2 on the Billboard Hot 100 without hitting #1: 2 wds. |
| 43% | OTIS | 4 | "Sitting on the dock of the Bay" singer, first name |
| 43% | CAROLEKING | 10 | Singer of the 1971 #1 hit song "It's Too Late" (2 wds.) |