| Text | Length |
| "Okay, ask away!" | 27 |
| "Okay, fine" | 22 |
| "Okay, gotcha!" | 25 |
| "Okay, I give up!" | 28 |
| "Okay, I'm up!" | 29 |
| "Okey-doke!" | 22 |
| "Okey-dokey" | 22 |
| "Oklahoma! "aunt | 26 |
| "Oklahoma!" Annie | 27 |
| "Oklahoma!" aunt | 26 |
| "Oklahoma!" bad guy | 29 |
| "Oklahoma!" baddie | 28 |
| "Oklahoma!" flirt | 27 |
| "Oklahoma!" gal | 25 |
| "Oklahoma!" girl | 26 |
| "Oklahoma!" hero | 26 |
| "Oklahoma!" prop | 26 |
| "Oklahoma!" prop? | 27 |
| "Oklahoma!" role | 26 |
| "Oklahoma!" song | 26 |
| "Oklahoma!" vehicle | 29 |
| "Oklahoma" aunt | 25 |
| "Ol' Blue Eyes" | 29 |
| "Ol' Blue ___" | 28 |
| "Olé!," say | 24 |
| "Old Blue Eyes" | 25 |
| "Old chap" preceder | 29 |
| "Old chap" relative | 29 |
| "Old Gray" creature | 29 |
| "Old Gray" one | 24 |
| "Old King ___" | 24 |
| "Old King" of rhyme | 29 |
| "Old Man Eloquent" | 28 |
| "Old pal" of song | 27 |
| "Old Scratch" | 23 |
| "Old Ski-Nose" | 24 |
| "Old Smokey" start | 28 |
| "Old song" preceder | 29 |
| "Old ___ Sky" | 23 |
| "Old" British buddy | 29 |
| "Old" combination | 27 |
| "Old" country | 23 |
| "Old" Disney dog | 26 |
| "Old" punches? | 24 |
| "Olde" emporium | 25 |
| "Ole!" recipient | 26 |
| "Ole!" relative | 25 |
| "Oliver Twist" fare | 29 |
| "Oliver Twist" food | 29 |
| "Oliver Twist" girl | 29 |
| "Oliver!" composer | 28 |
| "Oliver!" director | 28 |
| "Olympia" artist | 26 |
| "Olympia" painter | 27 |
| "Omertà " author | 28 |
| "OMG that is funny" | 29 |
| "OMG ur so funny!" | 28 |
| "OMG! Spare me!" | 26 |
| "OMG! Too funny!" | 27 |
| "OMG!" ancestor | 25 |
| "OMG!" of yore | 24 |
| "OMG!," old-style | 27 |
| "OMG!," quaintly | 26 |
| "OMG, too funny!" | 27 |
| "OMG, yes!!!1" | 24 |
| "Omigosh!" [1938] | 27 |
| "Omnes viri regis" | 28 |
| "Omnia vincit __" | 27 |
| "Omnia vincit ___" | 28 |
| "Omnibus" host | 24 |
| "Omoo" island | 23 |
| "Omoo" setting | 24 |
| "On a ___ China" | 26 |
| "On a ___ Day" | 24 |
| "On Boxing" author | 28 |
| "On call" device | 26 |
| "On Golden __" | 24 |
| "On Golden ___" | 25 |
| "On Liberty" author | 29 |
| "On my honor!" | 24 |
| "On my honor" | 23 |
| "On Point" network | 28 |
| "On Point" station | 28 |
| "On tap" drinks | 25 |
| "On tap" order | 24 |
| "On the Beach" | 24 |
| "On the contrary!" | 28 |
| "On the contrary" | 27 |
| "On the double!" | 26 |
| "On the house" | 24 |
| "On the Isle ___" | 27 |
| "On the other hand" | 29 |
| "On the run" is one | 29 |
| "On the Town" actor | 29 |
| "On the Town" theme | 29 |
| "On the wagon" | 24 |
| "On top of that" | 26 |
| "On top of that..." | 29 |
| "On what date?" | 25 |
| "On Wings ___" | 24 |
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