| 100% | LOOKBEFOREYOULEAP | 17 | "He who hesitates is lost, but ..." |
| 100% | LOOKBEFOREYOULEAP | 17 | He who hesitates is lost, but also... |
| 73% | OLDSAW | 6 | "He who hesitates is lost," e.g. |
| 73% | MAXIM | 5 | "He who hesitates is lost," e.g. |
| 73% | OLDSAW | 6 | "He who hesitates is lost," for one |
| 62% | HES | 3 | He who ___itates is lost |
| 55% | WHO | 3 | "He ___ hesitates is lost" |
| 51% | HEWHO | 5 | ''__ hesitates is lost'' |
| 50% | KANYEWEST | 9 | About whom Obama said "He is a jackass. But he's talented" |
| 46% | HENRYFORD | 9 | He who wrote History is bunk |
| 46% | VOLDEMORT | 9 | He Who Must Not Be Named |
| 44% | RONALDINHO | 10 | Brazilian footballer who lost Coca-Cola as a sponsor after he was caught drinking Pepsi in a news conference |
| 44% | JENNIFERLOPEZ | 13 | Singer who was nominated for a Grammy for Best Dance Recording in 2000 but lost to Cher: 2 wds. |
| 44% | TENDERLY | 8 | He who handles a nettle __ is soonest stung |
| 44% | TRAVISSCOTT | 11 | Rapper who was nominated for a Grammy for Best Rap Album in 2019 but lost to Cardi B: 2 wds. |
| 44% | TAYLORSWIFT | 11 | Singer who was nominated for a Grammy for Best New Artist in 2008 but lost to Amy Winehouse: 2 wds. |
| 43% | WALDO | 5 | He was lost in books |
| 43% | ONCE | 4 | "I ___ was lost, but now am found" ("Amazing Grace" lyric) |
| 43% | MAO | 3 | He who said "A revolution is not a dinner party" |
| 42% | OTHELLO | 7 | He who “loved not wisely but too well” |
| 41% | OAF | 3 | One on whom subtlety is lost |
| 40% | SHEER | 5 | That woman may hesitate but is transparent |
| 40% | JESSICAPEGULA | 13 | American tennis pro who was the No. 3 seed at the 2023 US Open but lost to 26-Across in the fourth round (2 wds.) |
| 40% | CARR | 4 | Vikki who sang "It Must Be Him" |
| 40% | CARR | 4 | Vikki who sang “It Must Be Him” |
| 39% | BORIS | 5 | He was succeeded by Liz, who was succeeded by Rishi |
| 39% | ARES | 4 | He was on the losing side of the Trojan War |
| 39% | GETBACK | 7 | Song from 47-Across with the lyrics "Jojo was a man who thought he was a loner / But he knew it couldn't last" (2 wds.) |
| 39% | DOMINIC | 7 | Monaghan who was a Merry hobbit, got Lost |
| 39% | NERD | 4 | Someone who is great academically but socially inept |