| 100% | NOAH | 4 | He should have swatted those two flies |
| 49% | NOELCOWARD | 10 | He should have written "Fear of Flying" |
| 41% | JAMESHILTON | 11 | He should have written "Hotel" |
| 41% | JEFFREYARCHER | 13 | He should have written "Arrowsmith" |
| 40% | LOUISLAMOUR | 11 | He should have written "Love Story" |
| 39% | JONATHANSWIFT | 13 | He should have written "What Makes Sammy Run" |
| 39% | FRANCISBACON | 12 | He should have written "Green Eggs and Ham" |
| 39% | NORMANMAILER | 12 | He should have written "Postcards From the Edge" |
| 37% | SEEN | 4 | "I should have ___ that coming" |
| 35% | DUH | 3 | "I should have known that!" |
| 35% | AIRPLANE | 8 | Flying transport that has wings |
| 34% | DUH | 3 | ''I should have known that!'' |
| 34% | GREENEYES | 9 | Facial features that two per cent of people have |
| 34% | OREO | 4 | Cookie that has two wafers |
| 33% | TMI | 3 | "You should have kept that to yourself!": Abbr. |
| 33% | ACHILLES | 8 | He had a heel that wouldn't heal |
| 33% | PAPERAIRPLANE | 13 | Flier that might have something written on it |
| 33% | PANTS | 5 | What have two legs and fly? |
| 33% | LIL | 3 | Contraction that oughta have two apostrophes |
| 33% | ACE | 3 | Card that can have two values |
| 32% | MASTS | 5 | Poles that some sailboats have two of |
| 32% | DUH | 3 | "Oh, I should have known that!" |
| 32% | DUH | 3 | "Wow, I should have realized that!" |
| 32% | DUPLEX | 6 | A dwelling that has two residential units |
| 32% | RUNON | 5 | Sentence that should be two or more sentences |
| 32% | CAMEL | 5 | Animal that might have one hump or two |
| 32% | CAMEL | 5 | Animal that may have one hump or two |
| 32% | EPS | 3 | Items that may have two tracks, for short |
| 32% | ALIEN | 5 | 1979 Sigourney Weaver movie that had two sequels |
| 32% | UNO | 3 | Game that has Draw Two and Reverse cards |