| DAVIDBOWIE | Rock singer whose posthumous album "Blackstar" topped the charts in 2016: 2 wds. |
| RAYCHARLES | Soul singer whose posthumous album "Genius Loves Company" topped the charts in 2005: 2 wds. |
| MICHAEL | With 33-Across, pop singer whose posthumous album "This Is It" topped the charts in 2009 |
| BOWIE | Surname of the artist whose final album 'Blackstar' was released in 2016 (5) |
| OTISREDDING | US singer-songwriter whose posthumous album The Dock of the Bay was released in 1968 (4,7) |
| JASONALDEAN | Country singer whose album "They Don't Know" topped the Billboard 200 in 2016: 2 wds. |
| CORAL | Hoylake band, The ___, whose album, Magic And Medicine, topped the charts in 2003 (5) |
| KATEBUSH | Singer whose 1985 song Running Up That Hill topped the charts in 2022 after featuring in Stranger Things, pictured above (4,4) |
| HELLOGOODBYE | November 1967 Beatles single that topped the charts in the United States, the UK, France and Norway |
| SAYER | Singer/songwriter who topped the charts in the 1970s, Leo _ (5) |
| LORDE | Auckland-born singer who topped the charts in 2013 with Royals (5) |
| ADAMSKI | Dance music producer whose single Killer, introducing Seal as a vocalist, topped the charts in 1990 |
| SHANIATWAIN | That don't impress me much singer who received the Billboard Women in Music Icon Award in 2016: 2 wds. |
| GERRYRAFFERTY | Yacht rock singer whose hits include Baker Street and Right Down the Line: 2 wds. |
| TYRONNLUE | NBA coach for the Cavaliers who won the championship in 2016: 2 wds |
| ROBRIGGLE | The Hangover actor who played Colonel Sanders in commercials in 2016: 2 wds. |
| DOLLYPARTON | Jolene singer who received the CMAs' Willie Nelson Lifetime Achievement Award in 2016: 2 wds. |
| ONEWEEK | Barenaked Ladies hit, or how long it topped the charts in 1998 |
| PETERSANDLEE | Opportunity Knocks winners who topped the charts in 1973 with Welcome Home |
| ADAMFAITH | British teen idol who first topped the charts in 1959 |
