| Fictional skipper | 17 |
| Fictional sketch comedy series with Tracy Jordan and Jenna Maroney | 66 |
| Fictional skater Brinker | 24 |
| Fictional skater | 16 |
| Fictional sister of Meg Jo and Beth | 35 |
| Fictional Simon | 15 |
| Fictional Silver | 16 |
| Fictional silent film actress Desmond | 37 |
| Fictional Sicilian town in a Hersey novel | 41 |
| Fictional Sicilian town in a 1944 novel | 39 |
| Fictional Siam visitor | 22 |
| Fictional ship of note | 22 |
| Fictional ship | 14 |
| Fictional sergeant | 18 |
| Fictional secret agent Williams | 31 |
| Fictional secret agent who was a master of judo | 47 |
| Fictional secret agent | 22 |
| Fictional second self | 21 |
| Fictional seaman and theme of puzzle | 36 |
| Fictional sea hunter | 20 |
| Fictional school whose motto is "Draco dormiens nunquam titillandus" | 78 |
| Fictional Schnauzer of literature | 33 |
| Fictional Scarlett | 18 |
| Fictional Saxon knight | 22 |
| Fictional Sawyer | 16 |
| Fictional salesman Willy | 24 |
| Fictional salesman who said "I am not a dime a dozen!" | 64 |
| Fictional salesman of '80s ads | 34 |
| Fictional salesman | 18 |
| Fictional sailor's Thanksgiving mantra? | 43 |
| Fictional sailor | 16 |
| Fictional rubber | 16 |
| Fictional Roger or Peter | 24 |
| Fictional rodent | 16 |
| Fictional river of verse | 24 |
| Fictional river | 15 |
| Fictional ringbearer | 20 |
| Fictional ring bearer | 21 |
| Fictional reporter Lois | 23 |
| Fictional reporter Kent | 23 |
| Fictional reporter Brenda | 25 |
| Fictional reporter | 18 |
| Fictional rank above Padawan | 28 |
| Fictional ragamuffin | 20 |
| Fictional rafter | 16 |
| Fictional racer | 15 |
| Fictional race whose name means "My God" in Aramaic | 61 |
| Fictional race descended from humans | 36 |
| Fictional race | 14 |
| Fictional rabbit's lament | 29 |
| Fictional rabbit chaser | 23 |
| Fictional rabbit | 16 |
| Fictional Queen | 15 |
| Fictional Quaker captain | 24 |
| Fictional Pulitzer-winning journalist in a 2006 film | 52 |
| Fictional psychiatrist | 22 |
| Fictional protector of Truffula trees | 37 |
| Fictional private detective on NPR's "A Prairie Home Companion" | 77 |
| Fictional prisoner's location | 33 |
| Fictional princess | 18 |
| Fictional Prince Edward Island community | 40 |
| Fictional Potter | 16 |
| Fictional portal | 16 |
| Fictional pool hustler Fats | 27 |
| Fictional pooch | 15 |
| Fictional Plaza juvenile | 24 |
| Fictional Plaza Hotel resident | 30 |
| Fictional Plaza Hotel girl | 26 |
| Fictional Plaza Hotel brat | 26 |
| Fictional Plaza denizen | 23 |
| Fictional plantation owner | 26 |
| Fictional plantation of Georgia | 31 |
| Fictional plantation near Jonesboro, Georgia | 44 |
| Fictional plantation | 20 |
| Fictional planet of classic TV | 30 |
| Fictional planet in "Flash Gordon" | 44 |
| Fictional planet | 16 |
| Fictional Place | 15 |
| Fictional pizzeria in Bedford-Stuyvesant | 40 |
| Fictional pitchman whom Michael Dukakis likened to George H.W. Bush during a debate | 83 |
| Fictional pirate | 16 |
| Fictional pilot who said, "Never tell me the odds" | 60 |
| Fictional piece | 15 |
| Fictional picnic crasher | 24 |
| Fictional physician | 19 |
| Fictional phonetician, to his protégé | 43 |
| Fictional Philadelphia boxer | 28 |
| Fictional phantom | 17 |
| Fictional Petrie (3) | 20 |
| Fictional Perry | 15 |
| Fictional password user | 23 |
| Fictional parrot type featured in Monty Python's "dead parrot sketch" | 83 |
| Fictional parks department director of Pawnee, Indiana | 54 |
| Fictional park that's out of sight? (with ''The'') | 70 |
| Fictional pair | 14 |
| Fictional painter | 17 |
| Fictional pachyderm | 19 |
| Fictional owner of a tonsorial parlor | 37 |
| Fictional overseer of slaves | 28 |
| Fictional outlaw | 16 |