| 100% | BRYSONTILLER | 12 | "Don't" singer featured on 18-Across: 2 wds. |
| 60% | RIHANNA | 7 | "Work" singer featured on 18-Across |
| 58% | CHARLIXCX | 9 | Singer featured on Icona Pop's 2012 hit "I Love It": 2 wds. |
| 57% | STEVIEWONDER | 12 | "Superstition" singer featured on "That's What Friends Are For": 2 wds. |
| 57% | CHARLIXCX | 9 | Pop singer featured on Iggy Azalea's 2014 #1 song "Fancy": 2 wds. |
| 56% | BRUNOMARS | 9 | Pop singer featured on Mark Ronson's 2015 #1 song "Uptown Funk": 2 wds. |
| 56% | ELVISPRESLEY | 12 | "Jailhouse Rock" singer featured on postage stamps in both 1993 and 2015: 2 wds. |
| 55% | ALICIAKEYS | 10 | "No One" singer featured on the 2009 Jay Z hit "Empire State of Mind": 2 wds. |
| 54% | HARRYANDERSON | 13 | Actor who played Judge Stone on 18-Across: 2 wds. |
| 54% | GERALDMCRANEY | 13 | "Major Dad" actor who costars on 18-Across: 2 wds. |
| 54% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer featured on 1985's "That's What Friends Are For": 2 wds. |
| 54% | NATERUESS | 9 | Indie pop singer featured on Pink's 2013 #1 song "Just Give Me a Reason": 2 wds. |
| 54% | MICHAELBOLTON | 13 | "When a Man Loves a Woman" singer featured on the Lonely Island's "Jack Sparrow": 2 wds. |
| 54% | CHRISBROWN | 10 | "Forever" singer featured on three songs in Billboard's top 10 during a week in 2008: 2 wds. |
| 53% | WYCLEFJEAN | 10 | Fugees member featured on the Shakira hit single "Hips Don't Lie" (2 wds.) |
| 53% | MARKIEPOST | 10 | Actress who played public defender Christine Sullivan on 18-Across: 2 wds. |
| 53% | SEANGIAMBRONE | 13 | Actor who plays the geeky boy, Adam, on 18-Across: 2 wds. |
| 52% | BENNETTCERF | 11 | Random House publisher who was a regular panelist on 18-Across: 2 wds. |
| 52% | JUDITHLIGHT | 11 | "Transparent" actress who played Tony's employer Angela on 18-Across: 2 wds. |
| 52% | JULIANMCMAHON | 13 | "Nip/Tuck" actor who stars as Jess LaCroix on 18-Across: 2 wds. |
| 52% | WALTONGOGGINS | 13 | "Justified" actor who plays the main character Wade on 18-Across: 2 wds. |
| 52% | CLAIREDUNPHY | 12 | Julie Bowen has won two Emmys playing this character on 18-Across: 2 wds. |
| 52% | CAMERONTUCKER | 13 | Eric Stonestreet has won two Emmys playing this character on 18-Across: 2 wds. |
| 52% | ROSARIODAWSON | 13 | "Zombieland: Double Tap" actress who plays investigator Allegra Dill on 18-Across: 2 wds. |
| 51% | JOSEPHWAPNER | 12 | Original judge on 18-Across, from 1981 to 1993: 2 wds. |
| 51% | MARILYNMILIAN | 13 | Judge on 18-Across from 2001 to the present: 2 wds. |
| 51% | SELENAGOMEZ | 11 | 18-Across and 30-Across singer who plays Mabel Mora on "Only Murders in the Building" (2 wds.) |
| 51% | MINIATUREGOLF | 13 | Sport played on 18-Across (2 wds.) |
| 51% | ROBCORDDRY | 10 | Star of HBO's "Ballers" who plays Wade's friend Forrest on 18-Across: 2 wds. |
| 51% | KIMDICKENS | 10 | "Fear the Walking Dead" actress who plays police chief Eve Raytek on 18-Across: 2 wds. |