| RAYCHARLES | Soul singer whose posthumous album "Genius Loves Company" topped the charts in 2005: 2 wds. |
| DAVIDBOWIE | Rock singer whose posthumous album "Blackstar" topped the charts in 2016: 2 wds. |
| BROOKSANDDUNN | Duo whose "Play Something Country" hit #1 on the Billboard Country Songs Chart in 2005: 3 wds. |
| MICHAEL | With 33-Across, pop singer whose posthumous album "This Is It" topped the charts in 2009 |
| STEVEMARTIN | Father of the Bride actor who won the Mark Twain Prize for American Humor in 2005: 2 wds. |
| OTISREDDING | US singer-songwriter whose posthumous album The Dock of the Bay was released in 1968 (4,7) |
| FRANKROBINSON | Orioles Hall of Famer who received the Presidential Medal of Freedom in 2005: 2 wds. |
| LIZAMINNELLI | Cabaret star who received the GLAAD Vanguard Award in 2005: 2 wds. |
| TIGERWOODS | 2019 Masters champion who had last won the tournament in 2005: 2 wds. |
| GEORGELUCAS | Star Wars director who received the AFI Life Achievement Award in 2005: 2 wds. |
| AUBREYPLAZA | Parks and Recreation actress who was an NBC page in 2005: 2 wds. |
| PETEBUTTIGIEG | Current Secretary of Transportation who received a Rhodes Scholarship in 2005: 2 wds. |
| GORDONRAMSAY | Host of reality TV's "Hell's Kitchen" since its premiere in 2005: 2 wds. |
| MELISSAONEIL | Calgary-born champion of "Canadian Idol" in 2005: 2 wds. |
| STEVIEWONDER | Soul singer whose 1976 album Songs in the Key of Life spent its first 13 weeks atop the Billboard 200: 2 wds. |
| GISELEBUNDCHEN | Brazilian supermodel who wore the bejeweled Victoria's Secret Fantasy Bra in in 2000 and 2005: 2 wds. |
| CORAL | Hoylake band, The ___, whose album, Magic And Medicine, topped the charts in 2003 (5) |
| JOHNROBERTS | First Supreme Court justice confirmed in the 21st century (2005): 2 wds. |
| SHERYLSWOOPES | Former Houston Comets player who was named the WNBA MVP in 2000 2002 and 2005: 2 wds. |
| KATEBUSH | Singer whose 1985 song Running Up That Hill topped the charts in 2022 after featuring in Stranger Things, pictured above (4,4) |
