| 100% | CALVINHARRIS | 12 | Featured artist on Rihanna's "We Found Love," the #6 song of the 2010s: 2 wds. |
| 60% | CARDIB | 6 | Featured artist on Maroon 5's "Girls Like You," the #5 song of the 2010s: 2 wds. |
| 58% | JUSTINBIEBER | 12 | Featured artist (along with Daddy Yankee) on Luis Fonsi's "Despacito," the #9 song of the 2010s: 2 wds. |
| 54% | BILLYRAYCYRUS | 13 | Featured artist on Lil Nas X's "Old Town Road," the #7 song of the 2010s: 3 wds. |
| 48% | KIMBRA | 6 | Featured artist on Gotye's "Somebody That I Used to Know," the #8 song of the 2010s |
| 43% | AMERICANWOMAN | 13 | Lenny Kravitz's cover song which featured on the soundtrack of the 1999 film "Austin Powers: The Spy Who Shagged Me": 2 wds. |
| 42% | LETME | 5 | "___ Love You," 2016 song by DJ Snake and Justin Bieber that featured on the Billboard Hot 100: 2 wds. |
| 40% | MAMMAMIA | 8 | Musical based on the songs of ABBA: 2 wds. |
| 40% | BEYONCEKNOWLES | 14 | Singer whose song "Crazy In Love" featuring Jay Z peaked at number one on the Billboard Hot 100 chart in 2003: 2 wds. |
| 39% | MARVINGAYE | 10 | Charlie Puth/Meghan Trainor song about the singer of "What's Going On": 2 wds. |
| 39% | KAMALAHARRIS | 12 | US vice president and #3 on Forbes's 2020 list of The World's 100 Most Powerful Women: 2 wds. |
| 39% | MICHAELBOLTON | 13 | "When a Man Loves a Woman" singer featured on the Lonely Island's "Jack Sparrow": 2 wds. |
| 38% | DAVIDCOOK | 9 | Singer of the 2008 song "Light On": 2 wds. |
| 38% | JEFFBEZOS | 9 | Amazon.com founder who's #12 on the 2013 Forbes List of Richest Americans ($27.2 billion): 2 wds, |
| 38% | SOCIALNETWORK | 13 | "The ___" 2010 biographical drama based on "The Accidental Billionaires," about the founding of Facebook: 2 wds. |
| 38% | IGGYAZALEA | 10 | Featured singer on the buttocks-themed song "Booty" with Jennifer Lopez: 2 wds. |
| 38% | JINGLEBELL | 10 | "___ Rock," Christmas song that was featured on the "Mean Girls" soundtrack: 2 wds. |
| 38% | PETERCETERA | 11 | Singer with the 1986 #1 song “Glory of Love”: 2 wds. |
| 38% | PROUDMARY | 9 | Girl in a Tina Turner song from the soundtrack of "What's Love Got to Do with It": 2 wds. |
| 37% | MACMILLER | 9 | Rapper featured on Ariana Grande's 2013 top 10 song "The Way": 2 wds. |
| 37% | ROBERTREDFORD | 13 | "The Sting" actor who played the love interest of Barbra Streisand's character in 1973's "The Way We Were": 2 wds. |
| 37% | BUDDYVALASTRO | 13 | Name of the head baker featured on 1-/5-Across: 2 wds. |
| 37% | PHILCOLLINS | 11 | Singer with the 1988 #1 song “Groovy Kind of Love”: 2 wds. |
| 37% | CHURCHBELLS | 11 | Chimes that beckon parishioners on Sunday morning ... or the title of a song on Carrie Underwood's latest album: 2 wds. |
| 37% | ITSOK | 5 | "___", song by Tom Rosenthal, featured in the trailers of "Comet" and "Anesthesia" : 2 wds. |
| 37% | LANACONDOR | 10 | "To All the Boys I've Loved Before" actress who guest-starred as Gregory's date on season 3 of "Abbott Elementary": 2 wds. |
| 37% | QUEENLATIFAH | 12 | Singer who performed "That's the Letter O" (a parody of "That's the Way We Flow") on "Sesame Street": 2 wds. |
| 37% | JASONALDEAN | 11 | Country singer named ACM's Artist of the Decade for the 2010s in 2019 (2 wds.) |
| 37% | GODIS | 5 | "___ a DJ," 2003 song by Pink that was featured on the "Mean Girls" soundtrack: 2 wds. |
| 37% | MADDENNFL | 9 | Video game franchise that featured 15-Across on the cover of the 2011 version: 2 wds. |