| ___ Sketch (classic drawing toy) | 32 |
| ___ Sketch | 10 |
| ___ Skelton, chairman of the House Armed Services Committee | 59 |
| ___ Skavinsky Skavar | 20 |
| ___ size (cut down) | 19 |
| ___ Six-Pack | 12 |
| ___ Six (Louisiana group who was the focus of 2007 rallies) | 59 |
| ___ Sisters of "Macbeth" | 34 |
| ___ Sisters (Shakespearean witches) | 35 |
| ___ Sisters (daughters of Atlas) | 32 |
| ___ Sisters | 11 |
| ___ sister | 10 |
| ___ sins | 8 |
| ___ sink | 8 |
| ___ sinister | 12 |
| ___ Sinha, Sanskrit poet | 24 |
| ___ singing | 11 |
| ___ sine qua non | 16 |
| ___ Sinclair (protagonist of Hesse's "Demian") | 60 |
| ___ since (as of) | 17 |
| ___ since | 9 |
| ___ Sinatras | 12 |
| ___ Simpson, Southern Open champ: 1985 | 38 |
| ___ simple | 10 |
| ___ Simeon, Calif. | 18 |
| ___ Simeon | 10 |
| ___ Simbel, on the Nile | 23 |
| ___ Simbel, Nile landmark | 25 |
| ___ Simbel, historic site in Egypt | 34 |
| ___ Simbel, historic Egyptian site | 34 |
| ___ Simbel, Egypt | 17 |
| ___ Simbel, Egypt | 18 |
| ___ Simbel (Egyptian temple site) | 33 |
| ___ Simbel | 10 |
| ___ Silvia, mother of Romulus and Remus | 39 |
| ___ silver platter | 18 |
| ___ silver (1890s political issue) | 34 |
| ___ silver | 10 |
| ___ silly question ... | 22 |
| ___ silly question | 18 |
| ___ Silence, 1989 Kentucky Derby winner | 39 |
| ___ Sigurdson (Eric Forman's grandmother on "That '70s Show") | 79 |
| ___ signum (see the proof) | 26 |
| ___ signum (look at the proof: Lat.) | 36 |
| ___ signum (here is the proof) | 30 |
| ___ signum | 10 |
| ___ signs | 9 |
| ___ sign (=) | 12 |
| ___ Sigma Phi (honor society) | 29 |
| ___ sigilli (seal's spot) | 29 |
| ___ sight (fantastic) | 21 |
| ___ sight | 9 |
| ___ sienna | 10 |
| ___ sides (everywhere) | 22 |
| ___ sides | 9 |
| ___ side of the tracks | 22 |
| ___ side (askew) | 16 |
| ___ siècle (decadent) | 24 |
| ___ siècle | 13 |
| ___ shui (Chinese practice) | 27 |
| ___ shui | 8 |
| ___ Shuffle (boxing move) | 25 |
| ___ Shuffle | 11 |
| ___ shu pork | 12 |
| ___ Shriver, sister of J.F.K. | 29 |
| ___ shrimp (what Sea-Monkeys are) | 33 |
| ___ shrike of Madagascar | 24 |
| ___ shrew | 9 |
| ___ shrdlu (printer's slug) | 31 |
| ___ shrdlu (printer's error) | 32 |
| ___ shrdlu | 10 |
| ___ shower (event where a couple rakes in the loot) | 51 |
| ___ show, at a carnival | 23 |
| ___ show (street carnival) | 26 |
| ___ show (spectacle) | 20 |
| ___ show (solo act) | 19 |
| ___ show (carnival) | 19 |
| ___ show (carnival attraction) | 30 |
| ___ show | 8 |
| ___ shoulders above | 19 |
| ___ shot, in hockey | 19 |
| ___ shot (punchline follow-up) | 30 |
| ___ shot (punch line follow-up) | 31 |
| ___ shot (joke follow-up) | 25 |
| ___ shot (drummer's quickie) | 32 |
| ___ shot | 8 |
| ___ shorts | 10 |
| ___ Shorthand course | 20 |
| ___ shorthair (cat breed) | 25 |
| ___ short (underestimate) | 25 |
| ___ short | 9 |
| ___ shoppers | 12 |
| ___ Shop Boys ("West End Girls" band) | 47 |
| ___ Shop Boys ("Go West" band) | 40 |
| ___ Shop Boys | 13 |
| ___ shop | 8 |
| ___ shooting | 12 |
| ___ shooter | 11 |
| ___ shoestring (with little to spend) | 37 |
| ___ shoestring (cheaply) | 24 |