| 100% | BAD | 3 | "___ Blood" (2015 Taylor Swift hit featuring Kendrick Lamar) |
| 83% | BAD | 3 | "___ Blood" (2015 Taylor Swift single featuring Kendrick Lamar) |
| 53% | WILDESTDREAMS | 13 | 2015 Taylor Swift hit whose title suggests bedtime: 2 wds. |
| 53% | LIKETHAT | 8 | 2024 Future hit featuring Kendrick Lamar: 2 wds. |
| 52% | BADBLOOD | 8 | Taylor Swift collaboration with Kendrick Lamar |
| 52% | CARDIGAN | 8 | Taylor Swift hit that features a sweater metaphor |
| 48% | BADBLOOD | 8 | Taylor Swift/Kendrick Lamar song that won the 2015 MTV VMA for Video of the Year: 2 wds. |
| 48% | STYLE | 5 | Taylor Swift hit on Billboard's 2015 year-end Hot 100 ... or fashion sense |
| 46% | OFUS | 4 | "Both ___" (B.o.B hit featuring Taylor Swift): 2 wds. |
| 46% | FOLKLORE | 8 | 2020 album by Taylor Swift featuring the hits "August" and "Cardigan" |
| 44% | DEDICATION | 10 | Hit single featuring Kendrick Lamar from the album 39-Across by 29-Across |
| 44% | SPEAK | 5 | "___ Now," 2010 album by Taylor Swift featuring the hits "Mine" and "Sparks Fly" |
| 43% | SQUABBLEUP | 10 | 2024 Kendrick Lamar hit featured in Mercedes-AMG's Formula One promotional campaign: 2 wds. |
| 43% | LOVER | 5 | 2019 album by Taylor Swift featuring the hits "Me!" and "You Need to Calm Down" |
| 42% | SHAKE | 5 | Taylor Swift hit song "___ It Off" |
| 41% | OUR | 3 | "__ Song": Taylor Swift hit |
| 41% | WILLOW | 6 | 2020 taylor swift hit |
| 41% | ANTI | 4 | "__-Hero": Taylor Swift hit |
| 41% | HERO | 4 | "Anti-___" (2022 Taylor Swift hit) |
| 41% | OUR | 3 | 2007 Taylor Swift hit "___ Song" |
| 41% | ITOFF | 5 | 2009 Taylor Swift hit, "Shake __" |
| 41% | BADBLOOD | 8 | 6x platinum Taylor Swift hit |
| 41% | ITOFF | 5 | 2014 Taylor Swift hit, "Shake __" |
| 41% | OUR | 3 | "___ Song" (early Taylor Swift hit) |
| 41% | ANTIHERO | 8 | 2022 Taylor Swift hit song |
| 41% | OUR | 3 | "___ Song" (2006 Taylor Swift hit) |
| 41% | TAYLORSWIFT | 11 | "Shake It Off" singer whose 2015 hit "Bad Blood" features 31-Across: 2 wds. |
| 41% | DONTWANNAKNOW | 13 | 2016 Maroon 5 hit single featuring Kendrick Lamar (3 wds.) |
| 39% | WILLOW | 6 | 2020 Taylor Swift hit; type of tree |
| 39% | IKNEW | 5 | “___ You Were Trouble” (2012 Taylor Swift hit) |