| 100% | ANKA | 4 | He had a #4 hit with "It's Time to Cry" |
| 51% | SNOOPDOGG | 9 | He had a 2004 #1 hit "Drop It Like It's Hot" |
| 50% | KRUPA | 5 | He had a 1941 hit with "Drum Boogie" |
| 50% | PSY | 3 | He had a 2012 hit with "Gangnam Style" |
| 48% | COLE | 4 | He had a 1948 #1 hit with "Nature Boy" |
| 48% | FATSWALLER | 10 | He had a hit with "The Joint Is Jumpin'" |
| 48% | LAW | 3 | It's said to have a long arm, with "the" |
| 47% | LOUBEGA | 7 | He had a hit with Mambo No. 5 in 1999 |
| 44% | LAUPER | 6 | Cyndi who had a 1983 hit with Time After Time |
| 44% | PITCH | 5 | It has the potential to be a hit |
| 43% | SAVAGE | 6 | __ Garden had a 1997 hit with To The Moon and Back |
| 43% | GORE | 4 | Lesley who had a hit with "It's My Party" |
| 42% | TSA | 3 | It has to deal with a lot of baggage, for short |
| 42% | REMEMBERTHEMAIZE | 16 | Historic cry with a kernel of truth to it? |
| 42% | LAKE | 4 | With a set playlist, it's time to pick a destination! (1/5) Large landlocked body of water, like Tahoe or Huron |
| 41% | ANKA | 4 | "It's Time to Cry" singer, 1959 |
| 41% | ENTERKEY | 8 | It's hit with a pinky |
| 41% | POLOBALL | 8 | It's hit with a mallet |
| 41% | DIPLO | 5 | American EDM DJ who had a 2019 hit with "Close to Me" |
| 40% | CHEAT | 5 | With 4-Down, time to eat brownies during a diet |
| 40% | TACO | 4 | With 42-Across, time to have a folded Mexican food |
| 40% | TUPAC | 5 | He had a beef with Biggie |
| 40% | ROGET | 5 | He had a way with words |
| 40% | OVERTIME | 8 | It's for those with a score to settle |
| 40% | GIN | 3 | It's mixed with vermouth to make a martini |
| 40% | JONAH | 5 | He had a whale of a time |
| 40% | THELAW | 6 | It's said to have a long arm |
| 39% | EER | 3 | Stretch of time it takes to get to doomsday, to those with a poetical bent |
| 39% | EIGHTHNOTE | 10 | It's played for half a beat in 4/4 time |
| 39% | SHADOW | 6 | It's used to tell the time on a sundial |