| 100% | KENNY | 5 | London-born singer-songwriter and actor who appears on the cover of 1973 album Band on the Run by Paul McCartney and Wings |
| 89% | KENNYLYNCH | 10 | London-born singer-songwriter and actor who appears on the cover of 1973 record album Band on the Run by Paul McCartney and Wings |
| 35% | RUN | 3 | "Band on the ___" (1973 Paul McCartney and Wings album) |
| 35% | JAMESTAYLOR | 11 | Singer/songwriter who appeared on the March 1, 1971, cover of Time Magazine with the headline "The New Rock: Bittersweet and Low" (2 wds.) |
| 34% | 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% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 31% | RUN | 3 | "Band on the ___" (Paul McCartney and Wings album) |
| 31% | BEVERLYSILLS | 12 | Singer/songwriter who appeared on the November 22, 1971, cover of Time Magazine with the corner banner "America's Queen of Opera" (2 wds.) |
| 31% | TOBY | 4 | Country singer Keith who appeared on the finales of "The Late Late Show With Craig Ferguson" and "The Colbert Report" |
| 30% | WARREN | 6 | With 35-Across, actor who played Clyde, one of the title characters on the run in 1967's "Bonnie and Clyde" |
| 30% | CHUCKBERRY | 10 | Rock-and-roll legend who appeared on the cover of Rolling Stone in its 50th year (2017) (2 wds.) |
| 30% | SAHL | 4 | Comedian who appeared on the cover of Time, 8/15/1960 |
| 30% | LANDON | 6 | Michael who appeared on the cover of TV Guide 22 times |
| 30% | SNOOKI | 6 | Reality TV star who appeared on the cover of Rolling Stone |
| 30% | ALEXISSMITH | 11 | Singer/actress who appeared on the May 3, 1971, cover of Time Magazine with the headline "That Old Magic Relights Broadway" (2 wds.) |
| 29% | MICHAEL | 7 | ___ Jackson and Paul McCartney, singers who collaborated on the song "Say Say Say" |
| 29% | THELONIOUSMONK | 14 | Jazz legend who appeared on the cover of "Time" magazine on February 28, 1964 (2 wds.) |
| 29% | WYNTONMARSALIS | 14 | Jazz legend who appeared on the cover of "Time" magazine on October 22, 1990 (2 wds.) |
| 29% | WONDER | 6 | Stevie ___ and Paul McCartney, singers who collaborated on the hit song "Ebony and Ivory" |
| 29% | LAUREN | 6 | With 33-Across, "American Gigolo" actress who appeared on the cover of Vogue 28 times |
| 29% | HARRISONFORD | 12 | "Indiana Jones and the Dial of Destiny" actor who plays Jimmy's mentor Paul on "Shrinking": 2 wds. |
| 28% | WEEZER | 6 | 14-Across, 19-Across, and 33-Across rock band whose self-titled albums are known by the colors of the album covers |
| 28% | NAOMAMPBELL | 11 | *Woman who was the first Black model to appear on the cover of Time |
| 28% | GIGI | 4 | Model Hadid who has appeared on the cover of "Vogue" more than 30 times |
| 28% | AMALCLOONEY | 11 | Humanitarian and barrister who appeared on a 2018 cover of Vogue |
| 27% | PAULMCCARTNEY | 13 | The Beatles and Wings singer-songwriter who was born June 18, 1942 (2 wds.) |
| 27% | LADYGAGA | 8 | Singer of 15-Across, 9-Down, and 22-Down who will appear in the 2018 remake of "A Star Is Born" (2 wds.) |
| 27% | EMMYLOUHARRIS | 13 | Country Music Hall of Fame singer who collaborated with 28-Across and 43-Across on the Grammy-winning 1987 album "Trio" (2 wds.) |
| 27% | HOMEWARDBOUND | 13 | Song by Simon & Garfunkel written by Paul Simon that originally appeared on the album "Parsley, Sage, Rosemary and Thyme": 2 wds. |