| 100% | WALTWHITMAN | 11 | "Song of Myself" poet who appeared on a five-cent postage stamp in 1940: 2 wds. |
| 57% | SYLVIAPLATH | 11 | "Daddy" poet who appeared on a Forever stamp in 2012: 2 wds. |
| 53% | EMILYDICKINSON | 14 | "I'm Nobody! Who are you?" poet who appeared on an eight-cent postage stamp in 1971: 2 wds. |
| 39% | WILMARUDOLPH | 12 | Track and field legend who appeared on 23-cent stamps in 2004: 2 wds. |
| 39% | WILLACATHER | 11 | "My Ántonia" novelist who was honored on a U.S. postage stamp in 1973 (2 wds.) |
| 38% | JOHNNYCASH | 10 | Country music legend honored on a postage stamp in 2013: 2 wds. |
| 38% | BABEZAHARIAS | 12 | Golf legend, née Didrikson, who appeared on 18-cent stamps in 1981: 2 wds. |
| 38% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 37% | ANNEHATHAWAY | 12 | "Interstellar" actress who appears in one of the stories on 27-Across (2 wds.) |
| 37% | CHUCKBERRY | 10 | Rock-and-roll legend who appeared on the cover of Rolling Stone in its 50th year (2017) (2 wds.) |
| 37% | JOHNSLATTERY | 12 | "Mad Men" actor who appears in one of the stories on 27-Across (2 wds.) |
| 37% | BOSTONCELTICS | 13 | NBA champions who appeared on Wheaties boxes in 2008: 2 wds. |
| 36% | SEANPENN | 8 | Two time Academy Award winning actor of "Mystic River" who appeared in a guest role on "Two and a Half Men": 2 wds. |
| 36% | ATLANTABRAVES | 13 | World Series champions who appeared on Wheaties boxes in 1995: 2 wds. |
| 36% | CLORISLEACHMAN | 14 | "Phyllis" actress who appeared on "The Twilight Zone" in 1961: 2 wds. |
| 36% | JOHNKEATS | 9 | Romantic poet who died at the age of 25, but left a lasting impression on the literary world through his odes like "To Autumn": 2 wds. |
| 36% | CHARLESBRONSON | 14 | "Death Wish" actor who appeared on "The Twilight Zone" in 1961: 2 wds. |
| 36% | ELVISSTOJKO | 11 | Canadian figure-skating champ who appeared in a Broadway production of "Chicago" in 2014: 2 wds. |
| 36% | WILLIAMSHATNER | 14 | "T.J. Hooker" actor who appeared on "The Twilight Zone" in 1960 and 1963: 2 wds. |
| 36% | SHEENAEASTON | 12 | Only artist who appears on screen while performing a James Bond theme song over the opening credits ("For Your Eyes Only") (2 wds.) |
| 35% | NICOLEKIDMAN | 12 | "Australia" actress who appears in a Chanel fragrance ad: 2 wds. |
| 35% | DRAYMONDGREEN | 13 | 2017 NBA Defensive Player of the Year who appears in "Space Jam 2: A New Legacy" (2 wds.) |
| 35% | PATRICKDUFFY | 12 | "Dallas" actor who appeared in a 1976 Taco Bell commercial: 2 wds. |
| 35% | CHARLIZETHERON | 14 | "Prometheus" actress who appears in a Christian Dior fragrance ad: 2 wds. |
| 35% | REBAMCENTIRE | 12 | "Sing It Now: Songs of Faith & Hope" Grammy winner who is a coach on season 25 of "The Voice" (2 wds.) |
| 35% | DOROTHYPARKER | 13 | "A Star Is Born" co-screenwriter who was honored on a U.S. postage stamp in 1992 (2 wds.) |
| 35% | LOUISARMSTRONG | 14 | Jazz legend who appeared on the cover of "Time" magazine on February 21, 1949, the first of only five jazz musicians to do so (2 wds.) |
| 35% | JONHAMM | 7 | "Mad Men" actor who appeared on the reality dating show "The Big Date" in 1996: 2 wds. |
| 34% | NOAHWEBSTER | 11 | Lexicographer on a 1958 U.S. commemorative postage stamp who was a special agent for the U.S. Post Office (2 wds.) |
| 34% | DAVIDBECKHAM | 12 | British soccer legend who appeared in a 2012 Burger King commercial: 2 wds. |