| 100% | WALKITTALKIT | 12 | 2018 song where Drake collaborated with Migos: 4 wds. |
| 74% | LOOKALIVE | 9 | 2018 song where Drake collaborated with BlocBoy JB: 2 wds. |
| 74% | YESINDEED | 9 | 2018 song where Drake collaborated with Lil Baby: 2 wds. |
| 33% | THEWEEKND | 9 | Singer who collaborated with Ariana Grande on their 2014 top 10 song "Love Me Harder": 2 wds. |
| 33% | NICEFORWHAT | 11 | 2018 Drake top 10 single that samples Lauryn Hill's song "Ex-Factor": 3 wds. |
| 33% | GODSPLAN | 8 | Drake song that was #1 on Billboard's 2018 Year-End Hot 100: 2 wds. |
| 32% | GIRLSWANTGIRLS | 14 | 2021 Drake song whose title starts and ends with the same word: 3 wds. |
| 32% | INMYFEELINGS | 12 | Drake song that spent 10 weeks at #1 on the Billboard Hot 100 in 2018 (3 wds.) |
| 32% | BETTERNOW | 9 | 2018 Post Malone song with the line, "Woulda gave you anything, woulda gave you everything": 2 wds. |
| 31% | DONOTDISTURB | 12 | Song from Drake's 2017 playlist, "More Life", where he reveals his struggles in daily life: 3 wds. |
| 31% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 31% | KENDRICKLAMAR | 13 | "To Pimp a Butterfly" rapper, who collaborated with Taylor Swift on "Bad Blood", a song from her fifth album: 2 wds. |
| 31% | HOKEYPOKEY | 10 | Group dance song where you "shake it all about" and ends with "that's what it's all about": 2 wds. |
| 30% | INMYFEELINGS | 12 | Drake song that replaced his own "Nice for What" at #1 on the charts on July 21, 2018: 3 wds. |
| 30% | INMYFEELINGS | 12 | Drake hit with a record-setting 116.2 million US streams in the week of July 28, 2018: 3 wds. |
| 30% | INMYFEELINGS | 12 | Drake's superhit song released in 2018 which inspired an Internet meme dance challenge known as the "Kiki Challenge": 3 wds. |
| 29% | THUNDERCLOUDS | 13 | 2018 pop song in which Sia collaborated with Labrinth and Diplo |
| 29% | SCARYHOURS | 10 | 2018 two-song Drake EP featuring the two tracks in this puzzle: 2 wds. |
| 29% | MISSME | 6 | Drake and Lil Wayne hit song with the lyrics "I know things have changed, know I used to be around more" (2 wds.) |
| 28% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 28% | LANADELREY | 10 | "Doin' Time" singer who collaborates with 27-Across and 35-Across on the 2019 "Charlie's Angels" theme song "Don't Call Me Angel" (3 wds.) |
| 28% | DEMIMOORE | 9 | 4-Down actress with a November birthday (2 wds.) |
| 27% | IMAMESS | 7 | 2018 song about celebrating yourself despite flaws: 3 wds. |
| 27% | LOVELIES | 8 | 2018 song by 38-Across featuring Khalid: 2 wds. |
| 27% | SHEILAE | 7 | Singer/percussionist who collaborated with Prince on "Purple Rain" (2 wds.) |
| 27% | IMA | 3 | "___ Slave 4 U" (Britney Spears hit song) (2 wds.) |
| 27% | TONELOC | 7 | Rapper with the 1989 song "Wild Thing": 2 wds. |
| 27% | BARRYMANILOW | 12 | "Piano man" with the hit song "Mandy": 2 wds. |
| 27% | THEONE | 6 | "Love ___ You're With" (1971 hit song): 2 wds. |
| 27% | LOUIELOUIE | 10 | 1963 Kingsmen song with a repetitive title: 2 wds. |