| 100% | FIREANDRAIN | 11 | 1970 song about two things "I've seen" on James Taylor's "Greatest Hits" album: 3 wds. |
| 41% | CAROLINA | 8 | With 35-Across, 1969 song about homesickness that's on James Taylor's "Greatest Hits" album |
| 39% | COUNTRYROAD | 11 | 1971 song with the lyrics "take to the highway" that's on James Taylor's "Greatest Hits" album: 2 wds. |
| 34% | BADIDEARIGHT | 12 | Song on Olivia Rodrigo's 2023 album "Guts" with the lyric "Yes, I know that he's my ex, but can't two people reconnect?" (3 wds.) |
| 32% | HEARTOFGOLD | 11 | Song on 40-Across's 1972 album "Harvest" that was his only #1 hit (3 wds.) |
| 31% | FIREANDRAIN | 11 | James Taylor "weather" song: 3 wds. |
| 31% | TELLMEWHY | 9 | First song on 40-Across's 1970 album "After the Gold Rush" (3 wds.) |
| 30% | AHOLD | 5 | The Miracles hit song "You've Really Got ___ on Me" (2 wds.) |
| 29% | PRINCE | 6 | Singer whose "Purple Rain" and a greatest hits compilation were Billboard's top two albums on May 7, 2016 |
| 28% | HIGHWAYTOHELL | 13 | AC/DC song about the trials of being on the road: 3 wds. |
| 28% | SHAKEITOFF | 10 | "1989 (Taylor's Version)" song about letting things go (3 wds.) |
| 28% | LOLA | 4 | 1970 Kinks hit on Rolling Stone's list of the 500 greatest songs of all time |
| 26% | CARDIGAN | 8 | Song on Taylor Swift’s “Folklore” album |
| 26% | BLANKSPACE | 10 | Something found on a tax form (or a Taylor Swift hit song) (2 wds.) |
| 26% | BRIGHTESTBLUE | 13 | 2020 album by 44-Across with the hit single "Worry About Me" (2 wds.) |
| 26% | WILLIENELSON | 12 | Country music legend whose 73rd solo studio album is "I Don't Know a Thing About Love: The Songs of 17-Across" (2 wds.) |
| 26% | LAVENDERHAZE | 12 | Taylor Swift hit song that begins, "Meet me at midnight" (2 wds.) |
| 26% | BEASTOFBURDEN | 13 | Song on the Rolling Stones' "Some Girls" album that's #443 on Rolling Stone magazine's list of the 500 Greatest Rock and Roll Songs of All Time (3 wds.) |
| 26% | MEPORTOBONITO | 13 | Top 10 song on Bad Bunny's album 45-Across whose title translates to "I'll Behave Myself" (3 wds.) |
| 26% | WILDESTDREAMS | 13 | Hit song by 30-Across from the album "1989" that begs, "Say you'll remember me" (2 wds.) |
| 26% | TRAVELINBAND | 12 | 1970 Creedence Clearwater Revival song about life on the road: 2 wds. |
| 25% | MYNAMEIS | 8 | Hit song on Eminem's 1999 album The Slim Shady LP |
| 25% | THEHIGHLIGHTS | 13 | 2021 greatest hits album by The Weeknd (2 wds.) |
| 25% | TINA | 4 | 2008 greatest hits album that includes the song "Proud Mary" |
| 25% | THIS | 4 | "___ Is Me Trying" (Taylor Swift song on the album "Folklore") |
| 25% | WOMAN | 5 | Hit song on Doja Cat’s “Planet Her” album |
| 25% | STUCKWITHYOU | 12 | Novella by romance writer/neuroscience professor Ali Hazelwood about two scientists trapped on an elevator (3 wds.) |
| 25% | GONNAMAKE | 9 | "___ It Through This Year," a song about New Year's by the Great Lake Swimmers: 2 wds. |
| 25% | BREAKMYHEART | 12 | Top 20 hit song by Dua Lipa on her 2020 album "Future Nostalgia" (3 wds.) |
| 25% | MARVINGAYE | 10 | Charlie Puth/Meghan Trainor song about the singer of "What's Going On": 2 wds. |