| 100% | MTA | 3 | Subway ridden by Charlie in a 1959 hit |
| 61% | MTA | 3 | What Charlie rides, in a 1959 hit |
| 56% | MTA | 3 | Where Charlie "may ride forever," in a 1959 hit |
| 47% | DONNA | 5 | Name sung after "Oh" in a 1959 hit |
| 43% | TANSHOES | 8 | Footwear in a 1959 Dodie Stevens hit |
| 41% | OPP | 3 | Acronym in a Naughty by Nature hit |
| 40% | TEENAGER | 8 | One "in love" in a 1959 top 5 hit |
| 39% | EILEEN | 6 | Title woman in a hit song by Dexys Midnight Runners |
| 39% | HAVANA | 6 | Title city in a 2017 #1 hit by Camila Cabello |
| 39% | PPPPOKERFACE | 12 | Refrain in a 2008 hit by Lady Gaga |
| 39% | MYGGGGENERATION | 15 | Refrain in a 1965 hit by the Who |
| 39% | CHCHCHCHCHANGES | 15 | Refrain in a 1971 hit by David Bowie |
| 39% | LALALALALOLA | 12 | Refrain in a 1970 hit by the Kinks |
| 39% | BUMBLEBEE | 9 | Yellow Volkswagen Beetle befriended by Charlie Watson in a "Transformers" film |
| 39% | SADIE | 5 | Title woman in a 1975 R&B hit by the Spinners |
| 39% | RAISIN | 6 | A __ in the Sun, 1959 play by Lorraine Hansberry |
| 38% | ANT | 3 | Insect briefly ridden by a character in Honey, I Shrunk the Kids |
| 38% | ONA | 3 | "Club goin' up ___ Tuesday" (refrain in a 2014 platinum hit by ILoveMakonnen) |
| 38% | MEN | 3 | What "it's raining" in a classic dance hit by the Weather Girls |
| 38% | KITE | 4 | Charlie Brown's toy "eaten" by a tree in "Peanuts" comics |
| 37% | JOANN | 5 | Title girl in a 1958 hit by the Playmates |
| 37% | ELENORE | 7 | Title girl in a 1968 hit by the Turtles |
| 37% | RHIANNON | 8 | Title woman in a 1976 hit single by Fleetwood Mac |
| 37% | MTA | 3 | 1959 hit song about "a man named Charlie" |
| 37% | SANTA | 5 | He rides in a sleigh pulled by reindeer |
| 37% | QUARTERTO | 9 | With 16-Across, title time in a 1961 #1 hit by Gary U.S. Bonds |
| 36% | ALAN | 4 | Charlie's brother in "Two and a Half Men," played by Jon Cryer |
| 36% | CRAZY | 5 | "___ in Love," a hit song by Beyonce featuring her husband Jay-Z |
| 36% | EXS | 3 | "All My ___ Live in Texas," a hit song by George Strait |
| 36% | BERNADETTE | 10 | Title woman in a 1967 hit single by the Four Tops |