| 100% | SETHMEYERS | 10 | "Late Night" host who hosted the ESPY Awards in 2010 and 2011: 2 wds. |
| 68% | JAMIEFOXX | 9 | "Django Unchained" star who hosted the ESPY Awards in 2003 and 2004: 2 wds. |
| 64% | LINDSEYVONN | 11 | Alpine skier who won the Best Female Athlete ESPY Award in 2010 and 2011: 2 wds. |
| 59% | JOELMCHALE | 10 | "The Great Indoors" actor who hosted the ESPY Awards in 2015: 2 wds. |
| 59% | KENANTHOMPSON | 13 | "Saturday Night Live" comedian who hosted the People's Choice Awards in 2021 and 2022: 2 wds. |
| 59% | ROBRIGGLE | 9 | Former "Daily Show" correspondent who hosted the ESPY Awards in 2012: 2 wds. |
| 56% | LORENAOCHOA | 11 | 2007 Women's British Open winner who received the Best Female Golfer ESPY Award in 2009 and 2010: 2 wds. |
| 56% | JIMMYKIMMEL | 11 | ABC late-night host who wears a suit and tie in the "Happy" video: 2 wds. |
| 55% | KENANTHOMPSON | 13 | "Saturday Night Live" comedian who hosted the Nickelodeon Kids' Choice Awards in 2021: 2 wds. |
| 54% | JOHNOLIVER | 10 | Comedian and late-night host who voices Steve the porcupine in 43-Across (2 wds.) |
| 54% | JAMESCORDEN | 11 | Late-night star who hosted the 2016 Tony Awards: 2 wds. |
| 53% | CAROLBURNETT | 12 | Comedian and variety show host who was awarded the Mark Twain Prize in 2013: 2 wds. |
| 52% | JOHNCENA | 8 | Professional wrestler and actor who hosted the Nickelodeon Kids' Choice Awards in 2017 and 2018: 2 wds. |
| 52% | ARIANADEBOSE | 12 | "West Side Story" Oscar winner who hosted the Tony Awards in 2022, 2023, and 2024 (2 wds.) |
| 51% | ELTONJOHN | 9 | "Rocket Man" singer who hosted and performed on "Saturday Night Live" in 2011: 2 wds. |
| 51% | KELSEYGRAMMER | 13 | Actor who played Dr. Frasier Crane in "Frasier" and "Cheers", and hosted the 1998 Grammy Awards: 2 wds. |
| 51% | SERENAWILLIAMS | 14 | Tennis player who won the Best Female Athlete ESPY Award in 2003 and 2013: 2 wds. |
| 51% | RONDAROUSEY | 11 | Mixed martial artist who won the Best Female Athlete ESPY Award in 2014 and 2015: 2 wds. |
| 50% | JIMMYKIMMEL | 11 | Late-night talk show host who voiced the father in "The Boss Baby": 2 wds. |
| 50% | LEBRONJAMES | 11 | Heat forward who won the NBA Most Valuable Player award in 2009, 2010, 2012, and 2013: 2 wds. |
| 50% | ANTHONYMACKIE | 13 | "The Falcon and the Winter Soldier" actor who hosted the 2021 ESPY Awards (2 wds.) |
| 50% | TRACYMORGAN | 11 | Former "Saturday Night Live" cast member who hosted the 2019 ESPY Awards ceremony (2 wds.) |
| 49% | WILLFERRELL | 11 | "Elf" actor and "Saturday Night Live" star who won the Mark Twain Prize for American Humor in 2011: 2 wds. |
| 49% | JAMESCORDEN | 11 | "The Late Late Show" host who voices the title character in 18-Across: 2 wds. |
| 49% | DJKHALED | 8 | "Higher" performer who hosted the Nickelodeon Kids' Choice Awards in 2019: 2 wds. |
| 49% | JOELMCHALE | 10 | "Community" actor who hosted the People's Choice Awards in 2017: 2 wds. |
| 48% | CONANOBRIEN | 11 | Longtime late-night host and former "SNL" writer who returned to host in 2001: 2 wds. |
| 48% | JOHNVELAZQUEZ | 13 | Jockey who won the Kentucky Derby in 2011 and 2017 (2 wds.) |
| 48% | CHARLESBARKLEY | 14 | Basketball Hall of Famer nicknamed "the Round Mound of Rebound" who hosted "SNL" in 1993, 2010, 2012, and 2018: 2 wds. |
| 48% | DEMILOVATO | 10 | "Sorry Not Sorry" singer who hosted the People's Choice Awards in 2020: 2 wds. |