| "Orlando Furioso" poet | 32 |
| "Orlando Furioso" author | 34 |
| "Orinoco Flow" vocalist | 33 |
| "Orinoco Flow" singer, 1989 | 37 |
| "Orinoco Flow" singer | 31 |
| "Orinoco Flow" New Age singer | 39 |
| "Orinoco Flow" artist | 31 |
| "Orinoco Flow (Sail Away)" singer | 43 |
| "Origins of Totalitarianism" author | 45 |
| "Origines" author | 27 |
| "Original, crispy or grilled?" co. | 44 |
| "Original Six" org. | 29 |
| "Original Sin" band | 29 |
| "Original or crispy?" org. | 36 |
| "Original or crispy" offerer | 38 |
| "Original Gangster" rapper | 36 |
| "Original father of harmony," per Beethoven, briefly | 62 |
| "Original Amateur Hour" host Mack | 43 |
| "Origin of ___" | 25 |
| "Oriental gift," said Tom ___ | 39 |
| "Orfeo," e.g. | 23 |
| "Orfeo" composer Luigi | 32 |
| "Orfeo" composer | 26 |
| "Orfeo ed Euridice," e.g. | 35 |
| "Orfeo ed Euridice" role | 34 |
| "Orfeo ed Euridice" god | 33 |
| "Ores" man | 20 |
| "Oregon Trail" fort | 29 |
| "Ordinary People" Oscar winner | 40 |
| "Ordinary People" actress | 35 |
| "Order" partner | 25 |
| "Order up!" shouter | 29 |
| "Order of ___ ..." | 28 |
| "Order of the Arrow" org. | 35 |
| "Order in the court!" punctuator | 42 |
| "Ordem e Progresso" nación | 39 |
| "Orca" actress | 24 |
| "Orare ___ laborare . . . " | 37 |
| "Oranges" sometimes referred to as monkey-brains | 58 |
| "Oranges & Lemons" rock group | 43 |
| "Orange-juice Gulch" | 30 |
| "Orange, Red, Yellow" painter Mark | 44 |
| "Orange" tea grade | 28 |
| "Orange" tea | 22 |
| "Orange" drink that's really black | 48 |
| "Orange" drink | 24 |
| "Orange Sky" singer Murdoch | 37 |
| "Orange Is the New Black" protagonist | 47 |
| "Orange Disaster #5" artist | 37 |
| "Oracular Spectacular" band | 37 |
| "Ora pro ___" | 23 |
| "Or" follower, in an ultimatum | 40 |
| "Or" follower | 23 |
| "Or ___" (ultimatum words) | 36 |
| "Or ___!" (words of a threat) | 39 |
| "Or ___!" (veiled threat) | 35 |
| "Or ___!" (threat) | 28 |
| "Or ___!" (threat ultimatum) | 38 |
| "Or ___!" (threat ending) | 35 |
| "Or ___!" (threat ender) | 34 |
| "Or ___!" (bully's words) | 39 |
| "Or ___!" | 19 |
| "Or ___ what?" | 24 |
| "Or ___ told..." | 26 |
| "Or ___ thought..." | 29 |
| "Or ___ thought" | 26 |
| "Or ___ thou guide Arcturus . . . ": Job 38:32 | 56 |
| "Or ___ swoon to death": Keats | 40 |
| "Or ___ froth amid the boundless main": Emily Brontë | 65 |
| "Or __!" (threat ender) | 33 |
| "Or __ thought" | 25 |
| "Or would you rather be ___?" (from "Swinging on a Star") | 77 |
| "Or what's a ___ for?": Browning | 46 |
| "Or what shall a man give in exchange for his ___?": Mark 8:37 | 72 |
| "Or to take ___ against a sea of troubles ...": Hamlet | 64 |
| "Or to take ___ against a sea . . . ": Hamlet | 55 |
| "Or to take arms against ___ of troubles..." | 54 |
| "Or to take arms against ___ of troubles" (Hamlet) | 60 |
| "Or that the Everlasting ___ fix'd/His canon . . . ": Hamlet | 74 |
| "Or softly lightens ___ her face": Byron | 50 |
| "Or lend ___ to Plato . . . ": Tennyson | 49 |
| "Or leave ___ but in the cup": Jonson | 47 |
| "Or idlest froth __ the boundless main": Emily Brontë | 66 |
| "Or else!" is one | 27 |
| "Or else!" | 20 |
| "Or else ___ despiser of good manners": Shak. | 55 |
| "Or ---!" | 19 |
| "Opus___" (work of God) | 33 |
| "Optimism is the content ___ men in high places": Fitzgerald | 70 |
| "Optics" author | 25 |
| "Opticks" writer | 26 |
| "Oprah & Friends" airer | 37 |
| "Oppression et Liberté" author Simone | 50 |
| "Oppression et Liberté" author | 43 |
| "Opposites Attract" Paula | 35 |
| "Opposites Attract" Abdul | 35 |
| "Opposed," in the boonies | 35 |
| "Opposed" | 19 |
| "Opinions are like ___, everyone's got one and they all think everyone else's stink" | 102 |
| "Operators are standing by" and "Call now!," e.g. | 69 |