| 100% | LADYDI | 6 | She was on the cover of back-to-back issues of Time in September 1997 |
| 52% | JAMAL | 5 | Journalist Khashoggi who was on the cover of Time in 2018 |
| 50% | ELLEMACPHERSON | 14 | Australian model who's been on the cover of the Sports Illustrated Swimsuit Issue five times: 2 wds. |
| 49% | KATEUPTON | 9 | "The Other Woman" actress who's been on the cover of the Sports Illustrated Swimsuit Issue four times: 2 wds. |
| 48% | TYRABANKS | 9 | "America's Next Top Model" creator who's been on the cover of the Sports Illustrated Swimsuit Issue three times: 2 wds. |
| 46% | NAOMAMPBELL | 11 | *Woman who was the first Black model to appear on the cover of Time |
| 46% | PEOPLEMAGAZINE | 14 | Mia Farrow was on the cover of its first issue |
| 46% | MARTHASTEWART | 13 | Entrepreneur and lifestyle guru who was on the cover of the Holiday 2011 issue of Vogue Knitting: 2 wds. |
| 46% | KATEMOSS | 8 | She's been on the cover of British Vogue more than anyone else |
| 44% | PRECIOUSLEE | 11 | Model on the cover of Vogue's 2021 September issue |
| 44% | JACKDEMPSEY | 11 | First athlete to appear on the cover of Time magazine |
| 44% | SAHL | 4 | First-ever comedian to appear on the cover of Time (1960) |
| 43% | LEBRONJAMES | 11 | N.B.A. star who was on the cover of Sports Illustrated while still in high school |
| 43% | DALI | 4 | 32-year-old artist pictured on the cover of Time magazine in 1936 |
| 42% | KRYSTENRITTER | 13 | "Jessica Jones" actress who was on the cover of the Late Winter 2018 issue of Vogue Knitting: 2 wds. |
| 42% | ELLE | 4 | Supermodel Macpherson who appeared five times on the cover of the Sports Illustrated Swimsuit Issue |
| 42% | LORD | 4 | "The ___ of the Rings," fantasy film series that you will get to experience on the big screen if you spend some time in the 2000s |
| 42% | SUE | 3 | WNBA great Bird who appeared with Megan Rapinoe on the cover of ESPN The Magazine's Body Issue in 2018 |
| 42% | MYGALSAL | 8 | In song she was "a wild sort of devil, but dead on the level" |
| 42% | ELLIOT | 6 | Page who became the first openly trans man to appear on the cover of Time magazine (2021) |
| 41% | ARCO | 4 | The phrase "Bach's ___ Pitcairn" was on the back of the shirt the lead zombie wore in George Romero's "Dawn of the Dead" |
| 41% | MIA | 3 | Actress Farrow who was on the first cover of People magazine in 1974 |
| 41% | MICHELLEOBAMA | 13 | Former First Lady and "Becoming" author who was on the cover of the Winter 2021/22 issue of Vogue Knitting: 2 wds. |
| 40% | AOL | 3 | Tech company that was the subject of a 1997 Time cover |
| 40% | YEPIMGAY | 8 | *Headline on the April 1997 cover of Time featuring Ellen DeGeneres |
| 40% | ERELONG | 7 | “Truth is the child of Time; ___ she shall appear to vindicate thee”: Kant |
| 40% | BREAKINGBAD | 11 | #3 on Rolling Stone's 100 Greatest TV Shows of All Time (as of 2016) ... and a hint to what the black squares are doing in four rows of this puzzle |
| 39% | YOU | 3 | Word representing individual content creators on the Internet who were declared Time "Person of the Year" in 2006 |
| 39% | KATE | 4 | Model/actress Upton on the cover of the 100th anniversary issue of "Vanity Fair" |
| 39% | BAD | 3 | "___ was the blood of the song in the cab / On your first trip to L.A." |