| 100% | JOANCRAWFORD | 12 | "What Ever Happened to Baby Jane?" Oscar nominee who presented the Oscar statuette to 25-Across at the 35th Academy Awards (2 wds.) |
| 42% | JOANCRAWFORD | 12 | Bette Davis’s costar in "What Ever Happened to Baby Jane?," who was born Lucille Fay LeSueur: 2 wds. |
| 40% | ANNEBANCROFT | 12 | "The Miracle Worker" star who won the Oscar for Best Actress at the 35th Academy Awards (2 wds.) |
| 40% | MILLIONDOLLAR | 13 | "___ Baby," movie directed by Clint Eastwood which received seven Oscar nominations at the 77th Academy Awards: 2 wds. |
| 36% | BUONO | 5 | Victor —, Best Actor in a Supporting Role Oscar nominee for What Ever Happened To Baby Jane? |
| 36% | DOLLYPARTON | 11 | "9 to 5" singer who won the Willie Nelson Lifetime Achievement Award at the 2016 CMA Awards: 2 wds. |
| 34% | AUSTINMAHONE | 12 | YouTube sensation who was the Artist to Watch at the 2013 MTV Video Music Awards: 2 wds. |
| 34% | CHLOEZHAO | 9 | 16-Across director who won an Academy Award for Best Director in 2021, becoming the first non-white woman to win a directing Oscar (2 wds.) |
| 33% | ROBINWILLIAMS | 13 | "Good Will Hunting" star awarded the Best Supporting Actor Oscar at the 70th Academy Awards (2 wds.) |
| 33% | HELENHUNT | 9 | "As Good as It Gets" star awarded the Best Actress Oscar at the 70th Academy Awards (2 wds.) |
| 32% | ANTHONYHOPKINS | 14 | "The Father" star who won an Academy Award for Best Actor in 2021, becoming the oldest person to win an acting Oscar (2 wds.) |
| 32% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 32% | PAULNEWMAN | 10 | "The Sting" star who received the Hersholt Humanitarian Award at the Oscars in 1994: 2 wds. |
| 32% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 32% | CLINTEASTWOOD | 13 | Oldest person to win the Best Director Oscar, at 74 (for "Million Dollar Baby"): 2 wds. |
| 31% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 31% | ANGELABASSETT | 13 | "What's Love Got to Do with It" Oscar nominee who earned an MFA from the Yale School of Drama in 1983 (2 wds.) |
| 31% | BETTE | 5 | Davis of "What Ever Happened to Baby Jane?" |
| 31% | PEGGYCASS | 9 | "Auntie Mame" Oscar nominee who was a regular "To Tell the Truth" panelist: 2 wds |
| 30% | BETTE | 5 | Actress Davis of "What Ever Happened to Baby Jane?" |
| 30% | JACKNICHOLSON | 13 | "As Good as It Gets" star awarded the Best Actor Oscar at the 70th Academy Awards (March 23, 1998) (2 wds.) |
| 30% | BETTE | 5 | Joan's "What Ever Happened to Baby Jane?" co-star |
| 30% | MOMSMABLEY | 10 | Trailblazing African American who was the first female comedian to perform at the Apollo Theater: 2 wds. |
| 30% | OSCARBUZZ | 9 | Speculation leading up to the Academy Awards: 2 wds. |
| 29% | STEFANEDBERG | 12 | Swedish tennis great who lost to 25-Across in the 1990 Australian Open (2 wds.) |
| 29% | AMELIAEARHART | 13 | Aviation pioneer who was the first woman to fly solo across the Atlantic: 2 wds. |
| 29% | LADYGAGA | 8 | Academy Award winner for "Shallow" who was the halftime headliner at the Super Bowl in 2017 (2 wds.) |
| 29% | PHILMICKELSON | 13 | Three-time Masters champion who was runner-up to 53-Across at the 2023 Masters Tournament (2 wds.) |
| 29% | GARYSINISE | 10 | "Forrest Gump" Oscar nominee who plays the father of 18-Across in 31-Across (2 wds.) |
| 29% | MIRANDALAMBERT | 14 | "Settling Down" singer who won Entertainer of the Year at the 2022 ACM Awards: 2 wds. |