| 100% | THEBIGAPPLE | 11 | Nickname for New York City that was first popularized by John Fitz Gerald and was a part of an ad campaign: 3 wds. |
| 35% | BROTHERLYLOVE | 13 | "The City of ___," nickname for Philadelphia which was also called "The City that Loves You Back" in an ad campaign: 2 wds. |
| 33% | CASTLESMADEOF | 13 | "___ Sand," a song by Jimi Hendrix that is about the temporary nature of existence and how nothing can be taken for granted: 3 wds. |
| 32% | APPLE | 5 | The Big ___, nickname for New York City, New York that was popularized in the '20s |
| 31% | ACTAFOOL | 8 | Single from Ludacris that was part of the soundtrack for "2 Fast 2 Furious," and was also nominated for a Grammy: 3 wds. |
| 31% | HOLDMYHAND | 10 | Duet by Michael Jackson and Akon (birthday today), that was part of "Michael," M.J.'s first posthumous album: 3 wds. |
| 31% | THEJEFFERSONS | 13 | Sitcom set in New York city that was a spin-off of "All in the Family" (2 wds.) |
| 31% | TOURDEFRANCE | 12 | Annual cycling race that ends at Champs-Elysees and is a part of the UCI World Tour: 3 wds. |
| 31% | JOHNFKENNEDY | 12 | 35th US president for whom a New York City airport was renamed in 1963: 3 wds. |
| 29% | GOTHAM | 6 | Nickname for New York City popularized by writer Washington Irving |
| 29% | BROOKLYNDECKER | 14 | "Grace and Frankie" actress whose first name is also a place in New York City (2 wds.) |
| 29% | ROOM | 4 | "The Locked ___," 1986 novel by Paul Auster that is a part of his New York trilogy |
| 28% | WALKONBY | 8 | Song by Burt Bacharach and 26-Across that was a hit for 15-Across in 1964: 3 wds. |
| 28% | CRAZYFORYOU | 11 | 1985 pop song by Madonna that is a part of the soundtrack to the film "Vision Quest": 3 wds. |
| 28% | OPENYOURHEART | 13 | 1986 dance-pop song by Madonna that is a part of her third studio album "True Blue": 3 wds. |
| 28% | LADYMARMALADE | 13 | A popular song that was covered by Christina Aguilera, Lil' Kim, Mya and Pink for the soundtrack of "Moulin Rouge!": 2 wds. |
| 28% | THELATESHOW | 11 | Previously hosted by David Letterman, and now starring Stephen Colbert, CBS talk-show that was a fierce competitor of 40-Across: 3 wds. |
| 28% | LIKEAPRAYER | 11 | 1989 pop rock song by Madonna that is a part of her fourth studio album of the same name: 3 wds. |
| 28% | HOLYGHOST | 9 | Book by John Sandford which was part of the "Virgil Flowers" novel series and became a NYT 2018 Bestseller: 2 wds. |
| 27% | SIN | 3 | ___ City, nickname for Las Vegas, Nevada that is inspired by its nightlife and entertainment |
| 27% | WARMBLOOD | 9 | 2015 song by Carly Rae Jepsen which is a part of the album "Emotion" and is co-produced by Scooter Braun: 2 wds. |
| 27% | LIES | 4 | "Love ___," hit song by Khalid and Normani which is a part of the soundtrack for "Love, Simon" |
| 27% | BADNEWSBEARS | 12 | Sports comedy, directed by Richard Linklater, based on an alcoholic baseball player and is also a reboot of 1976 film of the same name: 3 wds. |
| 27% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 26% | RUNAWAYWITHME | 13 | 2015 song by Carly Rae Jepsen which is a part of the album "Emotion" and is co-produced by Shellback: 4 wds. |
| 26% | OOOBABYBABY | 11 | 1965 hit by 32-Across and 42-Across that was a 1979 hit for Linda Ronstadt (3 wds.) |
| 26% | TYCO | 4 | Toy manufacturer that is well known for its model trains and is now a part of Mattel: Abbr. |
| 26% | LOVELY | 6 | Hit song by Khalid and Billie Eilish which is a part of the soundtrack for "13 Reasons Why" |
| 26% | SOURCANDY | 9 | 2009 song by Carly Rae Jepsen which is a part of the album "Tug of War" and is produced by Josh Ramsay: 2 wds. |
| 26% | TEL | 3 | Part of the name of an Israeli city that is followed by Aviv |