| "Should I call a doctor?" | 35 |
| "Should I deal you a hand?" | 37 |
| "Should I take that as __?" | 37 |
| "Should it be otherwise ..." | 38 |
| "Should that be the case ..." | 39 |
| "Should that be the case" | 35 |
| "Should that be the case..." | 38 |
| "Should that be true ..." | 35 |
| "Should that come to pass" | 36 |
| "Should that happen ..." | 34 |
| "Should we do something else now?" | 44 |
| "Should __ acquaintance ..." | 38 |
| "Should ___ acquaintance ..." | 39 |
| "Should ___ acquaintance be forgot ..." | 49 |
| "Should ___ concerned?" | 33 |
| "Should ___ shouldn't ... " | 41 |
| "Should ___ shouldn't ..." | 40 |
| "Shoulda been here sooner" | 36 |
| "Shoulda listened to me!" | 35 |
| "Shoulda thought of that" | 35 |
| "Shoulda, woulda, coulda" one | 39 |
| "Shoulda, woulda, coulda" thinker | 43 |
| "Shouldn't do that" | 33 |
| "Shouldn't have done that!" | 41 |
| "Shouldn't we ask the Penguin?" | 45 |
| "Shoutin' in Key" singer Mahal | 44 |
| "Shoutin' in Key" singer Taj | 42 |
| "Show Boat" (1936) standout | 37 |
| "Show Boat" author Ferber | 35 |
| "Show Boat" composer Jerome | 37 |
| "Show Boat" novelist Ferber | 37 |
| "Show Boat" show-stopper | 34 |
| "Show Boat" standout, 1936 | 36 |
| "Show Boat" torch song | 32 |
| "Show Boat" writer Ferber | 35 |
| "Show Me the Way" band | 32 |
| "Show me the ___" (advertising slogan) | 48 |
| "Show Me ___ Go Home," 1925 song | 42 |
| "Show Your Bones" Yeah Yeah ___ | 41 |
| "Showboat" author Ferber | 34 |
| "Showboat" composer Jerome | 36 |
| "Showgirls" main character Malone | 43 |
| "Showgirls"' Gershon | 34 |
| "Shrek!" author William | 33 |
| "Shropshire Lad" monogram | 35 |
| "Shroud" city of Italy | 32 |
| "Shrovetide Revelers" artist | 38 |
| "Shucks, you're too kind!" | 40 |
| "Shutter Island" author Lehane | 40 |
| "Shutupshutupshutupshutup," initially | 47 |
| "Shylock's Daughter" author | 41 |
| "Shyness is nice" song by the Smiths | 46 |
| "Si No Te Hubieras Ido" #1ers | 39 |
| "SI" or "GQ" | 32 |
| "Si, mi chiamano Mimi," e.g. | 38 |
| "Sic et Non" theologian | 33 |
| "Sic semper tyrannis!" crier | 38 |
| "Sic semper tyrannis" shouter | 39 |
| "Sic transit gloria ___" | 34 |
| "Sic ___ gloria mundi" | 32 |
| "Sick as a dog," for instance | 39 |
| "Sicko" filmmaker Michael | 35 |
| "Sicut ___ in principio" (church lyric) | 49 |
| "Sid & Nancy" director Alex | 41 |
| "Sid the Science Kid" network | 39 |
| "Siddhartha" author Hermann | 37 |
| "Siddhartha" author Hesse | 35 |
| "Siddhartha" novelist Hermann | 39 |
| "Siddhartha" writer Hermann | 37 |
| "Side by Side by Sondheim," e.g. | 42 |
| "Sidereus Nuncius" author | 35 |
| "Sidewalks of New York" start | 39 |
| "Sideways" actress Virginia | 37 |
| "Sideways" co-star Paul | 33 |
| "Sideways" Oscar nominee Virginia | 43 |
| "Sigh much, drink little, ___" | 40 |
| "Sight" or "over" ender | 43 |
| "Sighted sub, sank __": WWII message | 46 |
| "Sighted sub, sank ___" | 33 |
| "Sighted sub, sank ___" (WWII message) | 48 |
| "Sighted sub, sank _____" | 35 |
| "Sighted sub, ___ same" | 33 |
| "Sighted sub, ___ same": Mason | 40 |
| "Sighting" near Urquhart Castle | 41 |
| "Sign Your Name" Terence ___ D'Arby | 49 |
| "Sign ___ Times" (Prince song) | 40 |
| "Significant Other" band | 34 |
| "Signs of the Zodiac" artist | 38 |
| "Silas Marner" author George | 38 |
| "Silas Marner" creator | 32 |
| "Silas Marner" foundling | 34 |
| "Silas Marner" novelist | 33 |
| "Silas Marner" novelist George | 40 |
| "Silas Marner" writer George | 38 |
| "Silence of the Lambs" director | 41 |
| "Silence of the Lambs" role | 37 |
| "Silence of the Lambs" villain | 40 |
| "Silent All These Years" Amos | 39 |
| "Silent All These Years" Tori | 39 |
| "Silent migraine" symptom | 35 |