| 100% | LOEB | 4 | First unsigned artist to record a Billboard No. 1 hit |
| 66% | LOEB | 4 | Lisa ___ (first unsigned artist to have a Billboard No. 1 single) |
| 43% | TAKEONME | 8 | 1985 Billboard No. 1 hit with a heavily rotoscoped music video |
| 42% | ANNEMURRAY | 10 | First Canadian female solo artist to reach No. 1 on the U.S. Billboard Hot 100 |
| 42% | CHER | 4 | Only artist to have a #1 hit on any Billboard chart in six consecutive decades |
| 41% | KIMPETRAS | 9 | First openly transgender woman to have a No. 1 song on the Billboard Hot 100 chart |
| 41% | BILLIEEILISH | 12 | First artist born in the two-thousands to reach No. 1 on the Billboard Hot 100 (August, 2019) |
| 40% | WITHORWITHOUTYOU | 16 | First Billboard #1 hit for U2 ... and a hint to the answers to the four starred clues |
| 40% | BTS | 3 | First K-pop group to have a #1 Billboard hit |
| 39% | BILLIEEILISH | 12 | Youngest artist to record a James Bond theme song ("No Time to Die") (2 wds.) |
| 38% | WAP | 3 | 2020 No. 1 hit whose title acronym is compared to “macaroni in a pot” |
| 38% | DESPACITO | 9 | 2017 hit that was the first Spanish-language song to reach No. 1 on the Billboard Hot 100 since "Macarena" |
| 37% | SOLDIERBOY | 10 | *No. 1 hit for the Shirelles about a man sent off to war |
| 37% | ABBA | 4 | First group with a #1 Billboard hit, alphabetically |
| 36% | IAMWOMAN | 8 | First #1 Billboard hit by an Australian artist (1972) |
| 35% | ABBA | 4 | Alphabetically first pop group with a No. 1 hit |
| 35% | AHA | 3 | First Norwegian band to have a #1 hit in the US: Hyph. |
| 35% | ICEICEBABY | 10 | First single by a rapper to reach #1 on the Billboard Hot 100 |
| 34% | UNHOLY | 6 | Sam Smith and Kim Petras' 2022 song that became a Billboard No.1 hit |
| 34% | JONASBROTHERS | 13 | Artists on "Songland" whose "Sucker" was a #1 Billboard hit in 2019: 2 wds. |
| 34% | ADELE | 5 | First female singer to have three simultaneous top 10 hits as a lead artist |
| 34% | LORDE | 5 | Youngest solo artist to have a US #1 Billboard Hot 100 single |
| 34% | PSY | 3 | First music artist to have a video with a billion YouTube views |
| 34% | BONJOVI | 7 | First hard rock band to score a #1 country hit |
| 34% | RONSTADT | 8 | Recorded a number 1 version of You're No Good |
| 34% | FOUR | 4 | Number of #1 hits that Rihanna had in 2010 (the record for a female artist) |
| 33% | THEE | 4 | Megan ___ Stallion, rapper with two Billboard No. 1 hits in 2020 (“Savage,” “WAP”) |
| 33% | CARRIEUNDERWOOD | 15 | First country artist to debut atop the Billboard Hot 100 chart |
| 33% | ONEHIT | 6 | Bad artist to re-sign to a record deal |
| 33% | IWALKTHELINE | 12 | First #1 hit for 17-Across, which lent its name to a 2005 biopic: 4 wds. |