| 100% | TBONEBURNETT | 12 | Music legend who produced 14-Across and won a 2007 Grammy for Robert Plant and 47-Across's first collaboration, "Raising Sand" (3 wds.) |
| 34% | DAVIDBOWIE | 10 | Glam rock legend who won a posthumous Best Alternative Music Album Grammy in 2017 for "Blackstar": 2 wds. |
| 32% | LETSMAKELOVE | 12 | Duet by Faith Hill and Tim McGraw, released in 2000, that won the couple a Grammy for Best Country Collaboration with Vocals: 3 wds. |
| 31% | KISSMEKATE | 10 | 1948 Broadway show, with music and lyrics by 41-Across, that won the first Tony for Best Musical: 3 wds. |
| 30% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 30% | BEAUTIFULLIAR | 13 | Beyoncé and 36-Across song that won an MTV Video Music Award for Most Earthshattering Collaboration in 2007 (2 wds.) |
| 30% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 30% | PORKANDBEANS | 12 | Single by 42-Across whose video won a Grammy Award for Best Music Video in 2009 (3 wds.) |
| 30% | DONCHEADLE | 10 | "Hotel Rwanda" actor who won a 2022 Grammy for the audiobook of John Lewis's "Carry On": 2 wds. |
| 29% | WEFOUNDLOVE | 11 | Single from Rihanna's 6th studio album, a collaboration with DJ Calvin Harris, that won her a Grammy and was featured in "Sherlock" : 3 wds. |
| 29% | CHAINOFFOOLS | 12 | Aretha Franklin's 1967 single that won her a Grammy for Best Female R&B Vocal Performance and later a Grammy Hall Of Fame Award: 3 wds. |
| 29% | EDITHWHARTON | 12 | 13-Across and 25-Across writer who was the first woman to win a Pulitzer Prize in Literature, for her 1920 novel "The Age of Innocence" (2 wds.) |
| 28% | LADYGAGA | 8 | Singer who won a 2011 Grammy for "Bad Romance": 2 wds. |
| 28% | SPIKE | 5 | Jonze who won a Grammy Award for directing Fatboy Slim's "Weapon of Choice" music video |
| 28% | GWENJORGENSEN | 13 | American distance runner and two-time ITU World Champion who was the first to win a triathlon gold for USA in the Olympics: 2 wds. |
| 28% | ADELE | 5 | English singer-songwriter who won Grammy Awards for "25" and 14-Across |
| 28% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 28% | INDUSTRYBABY | 12 | 2021 #1 song by Lil Nas X and 36-Across that was nominated for a Best Melodic Rap Performance Grammy Award and won three MTV Video Music Awards (2 wds.) |
| 28% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 28% | RAISETHEROOF | 12 | 2021 collaborative album featuring Led Zeppelin lead singer Robert Plant and 47-Across (3 wds.) |
| 28% | KISSMEKATE | 10 | 1948 show with music and lyrics by 39-Across that won the first Tony Award for Best Musical (3 wds.) |
| 28% | HAYLEYMILLS | 11 | 17-Across and "The Parent Trap" star who won a Juvenile Oscar for "Pollyanna" (2 wds.) |
| 28% | CAROLEKING | 10 | "You've Got a Friend" singer/pianist who was the first woman to win a Grammy for Song of the Year (2 wds.) |
| 27% | CENT | 4 | 50 ___ (rapper who won a Grammy with Eminem and Dr. Dre for 2009's "Crack a Bottle") |
| 27% | SCHINDLERSLIST | 14 | 1993 film for which 46-Across won a Grammy Award and an Oscar (2 wds.) |
| 27% | JAMESEARLJONES | 14 | Actor who voiced Darth Vader and won two Tony Awards for Best Actor: 3 wds. |
| 27% | BETTERMAN | 9 | 2016 song written by Taylor Swift and performed by 33-Across that won a Grammy Award for Best Country Duo/Group Performance (2 wds.) |
| 27% | MARLONBRANDO | 12 | "On the Waterfront" Oscar winner who won (and declined) a Best Actor Oscar for playing Vito Corleone in 47-Across (2 wds.) |
| 27% | YOUMIGHTTHINK | 13 | The Cars Top 10 hit whose video features 44-Across as a housefly (and was the first to win the MTV Video Music Award for Video of the Year) (3 wds.) |
| 27% | JEFFDANIELS | 11 | Actor who won a 2013 Emmy for playing Will McAvoy, the anchor and managing editor on 37-Across: 2 wds. |