| 100% | BRR | 3 | "I should've worn my thermals!" |
| 76% | BRR | 3 | "I should've worn my mittens!" |
| 61% | BRRR | 4 | “I should have worn my winter coat!” |
| 55% | BRR | 3 | "I should've worn a jacket!" |
| 47% | BROWN | 5 | "If it is deemed necessary that I should forfeit my life . . ." orator |
| 46% | ERE | 3 | "I shall be much in years ___ I again behold my Romeo": Juliet |
| 45% | IDO | 3 | "What should ___ now?" ("Tell me my next step"): 2 wds. |
| 43% | BRR | 3 | "I should have worn a scarf!" |
| 42% | ORA | 3 | “Should I wear pants ___ skirt?” |
| 42% | ARIEL | 5 | "...my dainty ___! I shall miss thee": Prospero |
| 42% | MET | 3 | "I think I've ___ my match" |
| 41% | ISTHISABADTIMER | 15 | "Should I not use my oven clock?"? |
| 40% | OPRAH | 5 | Winfrey who said "I still have my feet on the ground, I just wear better shoes" |
| 39% | DUH | 3 | "I should've realized!" |
| 38% | DUH | 3 | "I should've known that!" |
| 38% | DUH | 3 | "I should've realized that!" |
| 38% | BRR | 3 | "Shoulda worn my jacket!" |
| 38% | ENTRANTRANT | 11 | "I should've won! I was robbed! It's all rigged!" and the like? |
| 38% | EVER | 4 | "If ___ I should leave..." |
| 38% | ELSE | 4 | "Anything ___ I should know?" |
| 38% | BTW | 3 | "Oh, I should mention ..." |
| 38% | IAGO | 4 | "I will wear my heart upon my sleeve" speaker, in Shakespeare |
| 38% | GROWN | 5 | "My, my, how you've ___ since I last saw you!" |
| 38% | LAYLA | 5 | "___, you've got me on my knees" (Clapton lyric) |
| 38% | OKILLBITE | 9 | "You've piqued my interest, tell me more" |
| 37% | DUHS | 4 | "I should've known that" comments |
| 37% | DUH | 3 | "I should've thought of that!" |
| 37% | FYI | 3 | "Thought I should share," briefly |
| 37% | SO | 2 | "And I should care ... why?" |
| 37% | OKSO | 4 | "And I should care because ...?" |