| 100% | WEIGHANKA | 9 | Measure a pop singer? |
| 65% | AUTOTUNES | 9 | Alters, as a pop singer's voice |
| 63% | DONHO | 5 | Honolulu-born jet pilot who became a pop singer |
| 62% | DANBROWN | 8 | The Da Vinci Code author was once a pop singer |
| 62% | RIHANNA | 7 | Pop singer from Barbados with a makeup line |
| 62% | KESHA | 5 | Pop singer once with a $ in her name |
| 61% | BLACKCATSTEVENS | 15 | ... a pop/folk singer with numerous 1970s hits? |
| 60% | SIA | 3 | Pop singer who released a remix album called "Cheap Thrills" |
| 60% | SIA | 3 | Pop singer known for performing in a face-obscuring wig |
| 59% | MADONNA | 7 | Pop singer who played Mae in A League of Their Own |
| 58% | VOCALIST | 8 | Singer with a pop group |
| 58% | TESSHARPERVALLICPA | 18 | If an actress wed a pop singer, then became an accountant, she'd be ___ |
| 57% | TICKLEDPINK | 11 | Amused a colorful pop-rock singer? |
| 56% | ELL | 3 | Country pop singer Lindsay whose last name is also a letter |
| 56% | MONTANA | 7 | "Hannah ___," Disney teen series starring Miley Cyrus as a pop singer who leads a double life |
| 55% | EROS | 4 | Italian pop singer Ramazzotti who shares his name with a Greek god |
| 54% | NELLYFURTADO | 12 | Pop singer who had a crossover hit with her 2006 electropop song "Maneater" (2 wds.) |
| 54% | MADONNA | 7 | Queen of Pop and singer of Like a Prayer |
| 53% | KESHA | 5 | Pop singer who used to use a dollar sign for the third letter of her name |
| 53% | ADAMLEVINE | 10 | American pop singer who shares a first name with older singer Ant: 2 wds. |
| 52% | LITTLEEVA | 9 | Pop singer whose version of "The Loco-Motion" inspired a dance craze in the 1960s: 2 wds. |
| 52% | KATYPERRY | 9 | "Dark Horse" pop singer who has never won a Grammy despite 13 nominations: 2 wds. |
| 52% | MADONNA | 7 | "Like A Virgin" pop singer |
| 51% | JOHNMAYER | 9 | Singer of the 2006 pop song "Gravity," which sounds like a waltz: 2 wds. |
| 50% | TAMESJAILER | 11 | Controls a prison guard like a pop singer? |
| 50% | NATERUESS | 9 | Indie pop singer featured on Pink's 2013 #1 song "Just Give Me a Reason": 2 wds. |
| 50% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 50% | CHER | 4 | A grammy winning singer nicknamed the "Goddess of Pop," who sang the hit song "Believe" |
| 50% | THEWEEKND | 9 | Singer of the 2015 pop song "Earned It," which sounds like a waltz: 2 wds. |
| 49% | IDOL | 4 | Widely adored pop singer |