| BLANK | With 30-Across Taylor Swift song that replaced her own Shake It Off at #1 on the charts on November 29 2014 |
| INMYFEELINGS | Drake song that replaced his own Nice for What at #1 on the charts on July 21 2018: 3 wds. |
| LOVEYOURSELF | Justin Bieber song that replaced his own Sorry at #1 on the charts on February 13 2016: 2 wds. |
| GLADSTONE | Good boys head off at 1 PM (9) |
| BLAKE | With 29-Across: Taylor Swift bestie who flew across the Atlantic to catch the show |
| BAD | With 35-Across, Taylor Swift hit that won the 2016 Best Music Video Grammy |
| ABC | Song that replaced "Let It Be" at #1 in 1970 |
| TIM | With 11-Across: Taylor Swift's first single, which she released in 2006 and which became a Top 40 hit |
| THELIFEOF | With 22 Across, Taylor Swift's upcoming 12th album, announced in August 2025 |
| IHADSOMEHELP | 2024 Post Malone song that debuted at #1 on the charts (4 wds.) |
| WILLOW | 2020 Taylor Swift song that debuted at #1 but fell 37 spots the following week |
| RED | Taylor Swift song that contains the line, "Fighting with him was like trying to solve a crossword an |
| SHAKEITOFF | 2014 Taylor Swift song that was just the 22nd ever to debut atop the Billboard Hot 100: 3 wds. |
| ALLTOOWELL | Taylor Swift song that Ryan Gosling performed a version of on "Saturday Night Live" over the weekend |
| YOUBELONGME | Taylor Swift song that won Best Female Video at the 2009 MTV Video Music Awards * (3,6,2) |
| FOLKLORE | Surprise Taylor Swift album that was released July 24 and debuted at #1 on the Billboard charts |
| NOTLIKEUS | 2024 Kendrick Lamar diss track that debuted at #1 on the charts (3 wds.) |
| OURS | 2010 Taylor Swift song that begins: "Elevator buttons and morning air / Strangers' silence makes me wanna take the stairs" |
| YOUARENOTALONE | Michael Jackson song that was the first ever to debut at #1 on the Billboard Hot 100 |
| ROCKYOURBABY | 1974 single by George McCrae that topped the charts on both sides of the Atlantic |
