| 100% | SHAKY | 5 | "Old ___": nickname of the Douglas C-124 Globemaster II, primary heavy-lift transport for MATS during the 1950s and early 1960s |
| 25% | DOOMSDAYDEFENSE | 15 | Nickname of the disruptive Dallas Cowboys lineup of the 1960s and '70s |
| 24% | JLO | 3 | Nickname of the singer known for "All I Have" and "On the Floor": 2 wds. |
| 24% | MAO | 3 | Leader of China in the 1950s, 1960s, and 1970s |
| 24% | MID | 3 | ___-century modern (design style of the 1950s and 1960s) |
| 24% | BELIEBER | 8 | Nickname for a fan of the singer of "Love Yourself" and "Sorry" |
| 24% | FDR | 3 | President during the start of World War II, for short |
| 23% | RSAILSPLITTER | 13 | Another nickname for Old Abe ... or a description of the circled letter? |
| 23% | SARAHVAUGHAN | 12 | Jazz singer of the 1940s and 1950s nicknamed "The Divine One": 2 wds. |
| 22% | NORIEGA | 7 | Military strongman and longtime C.I.A. informant captured during the U.S. invasion of Panama |
| 22% | BARTSTARR | 9 | Super Bowl I and II champion quarterback who played for the University of Alabama (2 wds.) |
| 22% | WILLIEMAYS | 10 | Outfielder for the Giants and two other teams in the 1940s, 1950s, 1960s, and 1970s: 2 wds. |
| 22% | TEDDY | 5 | Nickname of the elder President Roosevelt |
| 22% | ENGELBART | 9 | Douglas ___, American engineer and internet pioneer who is credited for the invention of computer mouse |
| 22% | OSCARS | 6 | Nickname of the Academy Awards for Film |
| 22% | BIGTHREE | 8 | Nickname for the dominant tennis trio of Roger Federer, Rafael Nadal, and Novak Djokovic: 2 wds. |
| 22% | IKE | 3 | Presidential nickname of the 1950s |
| 22% | REDICK | 6 | J.J. ___, former NBA player for Orlando Magic and host of the podcast "The Old Man And The Three" |
| 21% | ABE | 3 | Nickname of the President during the Civil War |
| 21% | CHARLES | 7 | Eldest son of the late Queen Elizabeth II |
| 21% | SHEA | 4 | Old home of the Mets and the Jets |
| 21% | IKE | 3 | Nickname of the president between Harry and Jack |
| 21% | NOLA | 4 | Nickname of the city known for Mardi Gras |
| 21% | ROCK | 4 | ___ and roll, music genre for Elvis Presley, which originated in Cleveland, Ohio, in the early 1950s |
| 21% | IKE | 3 | Oval Office nickname of the 1950s |
| 21% | ENOS | 4 | Son of Seth in the Old Testament who lived for nine hundred and five years |
| 21% | IKE | 3 | Nickname of the 1950s US president Dwight D. Eisenhower |
| 21% | DIAMONDJIMBRADY | 15 | Early railroad tycoon whose nickname is a hint to the starts of 17-, 23-, 51- and 62-Across |
| 21% | TEDDY | 5 | Presidential nickname of the early 20th century |
| 21% | IKE | 3 | Nickname of the 1950s president who was married to Mamie |