| 100% | ALLYEAR | 7 | ___ round (throughout the year): 2 wds. |
| 66% | BENBERNANKE | 11 | Economist who was Time's 2009 Person of the Year: 2 wds. |
| 65% | KEVINDURANT | 11 | NBA MVP in the year 2014: 2 wds. |
| 65% | VLADIMIRPUTIN | 13 | Russian leader who was Time's 2007 Person of the Year: 2 wds. |
| 65% | DONALDTRUMP | 11 | US leader who was Time's 2016 Person of the Year: 2 wds. |
| 65% | POPEFRANCIS | 11 | Vatican leader who was Time's 2013 Person of the Year: 2 wds. |
| 65% | DREWBREES | 9 | Quarterback who was Sports Illustrated's 2010 Sportsman of the Year: 2 wds. |
| 65% | LUKEBRYAN | 9 | "Strip It Down" singer and 2015 CMA Entertainer of the Year: 2 wds. |
| 65% | GRETATHUNBERG | 13 | Teen activist who was Time's 2019 Person of the Year: 2 wds. |
| 65% | ARIANAGRANDE | 12 | "Positions" singer who was Billboard's 2018 Woman of the Year: 2 wds. |
| 65% | STEPHONCASTLE | 13 | San Antonio Spurs guard named 2025 NBA Rookie of the Year: 2 wds. |
| 64% | STEELYDAN | 9 | "Reelin' in the Years" yacht rock band: 2 wds. |
| 64% | BILLIEEILISH | 12 | "Bad Guy" singer who was Billboard's 2019 Woman of the Year: 2 wds. |
| 64% | JALENBRUNSON | 12 | New York Knicks guard named 2025 NBA Clutch Player of the Year: 2 wds. |
| 64% | LIONELMESSI | 11 | Inter Miami captain who was Time's 2023 Athlete of the Year: 2 wds. |
| 64% | CAITLINCLARK | 12 | Indiana Fever player who was Time's 2024 Athlete of the Year: 2 wds. |
| 63% | THETERMINATOR | 13 | Time traveler sent to kill or protect Sarah Connor (depending on the year): 2 wds. |
| 63% | ARIANAGRANDE | 12 | "Thank U, Next" singer recognized as Billboard's 2018 Woman of the Year: 2 wds. |
| 63% | OLIVIARODRIGO | 13 | "Good 4 U" singer who was Billboard's 2021 Woman of the Year: 2 wds. |
| 63% | SIMONEBILES | 11 | Most decorated American gymnast who was Time's 2021 Athlete of the Year: 2 wds. |
| 63% | KANEBROWN | 9 | "Homesick" singer chosen as one of six 2022 CMT Artists of the Year: 2 wds. |
| 62% | SELMABLAIR | 10 | "Cruel Intentions" actress who was one of Glamour's 2023 Women of the Year: 2 wds. |
| 62% | LUKECOMBS | 9 | "Fast Car" singer chosen as one of six 2022 CMT Artists of the Year: 2 wds. |
| 62% | WINELABEL | 9 | Bottle wrapper that displays the year of your burgundy, say: 2 wds. |
| 61% | JODIEFOSTER | 11 | Two-time Oscar-winning actress who was Entertainment Weekly's 1991 Entertainer of the Year: 2 wds. |
| 61% | KACEYMUSGRAVES | 14 | "Follow Your Arrow" singer who is one of Time's 2022 Women of the Year: 2 wds. |
| 61% | DAKPRESCOTT | 11 | Associated Press's NFL Offensive Rookie of the Year for 2016: 2 wds. |
| 61% | DOLLYPARTON | 11 | "Jolene" singer who was MusiCares Person of the Year in 2019: 2 wds. |
| 60% | PATRICKMAHOMES | 14 | Kansas City Chiefs quarterback and co-winner of Sports Illustrated's 2020 Sportsperson of the Year: 2 wds. |
| 60% | QUINTABRUNSON | 13 | "Abbott Elementary" creator and star who was one of Glamour's 2023 Women of the Year: 2 wds. |