| 100% | KEITHRICHARDS | 13 | The Rolling Stones guitarist, who has appeared in the "Pirates of the Caribbean" series as Captain Teague, father of Jack Sparrow: 2 wds. |
| 60% | KEITHRICHARDS | 13 | Guitarist of "The Rolling Stones" who cameoed in "Pirates of the Caribbean: At World's End" as Captain Edward Teague: 2 wds. |
| 51% | KEITHRICHARDS | 13 | Rolling Stones guitarist who played a pirate in the third and fourth "Pirates of the Caribbean" films: 2 wds. |
| 45% | BLACKPEARL | 10 | Fictional pirate ship captained by Johnny Depp as Jack Sparrow in the "Pirates of the Caribbean" films (2 wds.) |
| 39% | SPARROW | 7 | Captain Jack ___, fictional pirate played by Johnny Depp in the "Pirates of the Caribbean" film series |
| 39% | JAVIERBARDEM | 12 | "Skyfall" villain portrayer who plays Captain Salazar in "Pirates of the Caribbean: Dead Men Tell No Tales": 2 wds. |
| 39% | GEOFFREYRUSH | 12 | "Shine" actor who plays Captain Hector Barbossa in "Pirates of the Caribbean: Dead Men Tell No Tales": 2 wds. |
| 39% | ORLANDOBLOOM | 12 | "Troy" actor who plays Captain Will Turner in "Pirates of the Caribbean: Dead Men Tell No Tales": 2 wds. |
| 39% | JOHNNYDEPP | 10 | "Black Mass" actor who plays a pirate in the "Pirates of the Caribbean" films: 2 wds. |
| 38% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 38% | JACKSPARROW | 11 | Pirate captain played by Johnny Depp in "Pirates of the Caribbean": 2 wds. |
| 37% | CHUCKBERRY | 10 | Rock-and-roll legend who appeared on the cover of Rolling Stone in its 50th year (2017) (2 wds.) |
| 36% | CROOK | 5 | Mackenzie —, actor-comedian who played Ragetti in the Pirates of the Caribbean film series |
| 36% | CROOK | 5 | Mackenzie —, actor and comedian who played Ragetti in the Pirates of the Caribbean film series |
| 36% | SPARROW | 7 | Jack ___, character played by Johnny Depp in the "Pirates of the Caribbean" film series who sports a distinctive braided beard |
| 36% | MATTDAMON | 9 | "The Martian" actor who has played in the World Series of Poker (2 wds.) |
| 36% | MICKJAGGER | 10 | Lead singer of the Rolling Stones who was knighted in 2003: 2 wds. |
| 36% | KEVINHART | 9 | "Jumanji" actor who has played in the World Series of Poker (2 wds.) |
| 35% | JACKSPARROW | 11 | Pirate played by Johnny Depp in the "Pirates of the Caribbean" movies: 2 wds. |
| 35% | AARONPAUL | 9 | "Breaking Bad" actor who has played in the World Series of Poker (2 wds.) |
| 35% | RAYROMANO | 9 | "Get Shorty" actor who has played in the World Series of Poker (2 wds.) |
| 35% | JACKSPARROW | 11 | Rakish captain in "Pirates of the Caribbean" whose last name is a kind of bird: 2 wds. |
| 35% | ZOESALDANA | 10 | "Avatar" actress who played a pirate in the first "Pirates of the Caribbean" film: 2 wds. |
| 35% | NANCYWILSON | 11 | One of Rolling Stone's "250 Greatest Guitarists of All Time," she plays guitar in the rock group Heart: 2 wds. |
| 35% | ORLANDOBLOOM | 12 | Actor who starred in both the "Pirates of the Caribbean" and "Lord of the Rings" movie franchises: 2 wds. |
| 35% | METYOURMOTHER | 13 | "How I ___," a popular TV series in which John Lithgow appeared as the father of Barney Stinson: 3 wds. |
| 35% | ORLANDOBLOOM | 12 | "Pirates of the Caribbean" actor who has been a UN Goodwill Ambassador for children: 2 wds. |
| 35% | ORLANDOBLOOM | 12 | "Pirates of the Caribbean" actor who plays marketing executive Danny Moore in "Gran Turismo": 2 wds. |
| 34% | WORF | 4 | Character who has appeared in the most episodes of the various "Star Trek" series |
| 34% | TEDDYROOSEVELT | 14 | Mascot in jersey #26 who has the least overall wins (138 as of 2020) of the four main 16-Across competitors: 2 wds. |