| Like an optimist's outlook | 30 |
| Like an optimist's glasses? | 31 |
| Like an optimist's glass | 28 |
| Like an opossum's tail | 26 |
| Like an opera song | 18 |
| Like an open secret | 19 |
| Like an open pasture | 20 |
| Like an open bottle of champagne | 32 |
| Like an onion in a Gibson | 25 |
| Like an omelet, e.g. | 20 |
| Like an omelet | 14 |
| Like an old wristwatch? | 23 |
| Like an old wristwatch, in more ways that one | 45 |
| Like an old woman | 17 |
| Like an old TV: Abbr. | 21 |
| Like an old tree trunk | 22 |
| Like an old sweater | 19 |
| Like an old sofa | 16 |
| Like an old schoolhouse | 23 |
| Like an old saw | 15 |
| Like an old record | 18 |
| Like an old print job | 21 |
| Like an old piano | 17 |
| Like an old pay telephone call | 30 |
| Like an old oak tree | 20 |
| Like an old Norse poem | 22 |
| Like an old mattress | 20 |
| Like an old man? | 16 |
| Like an old look looking good again | 35 |
| Like an old loaf | 16 |
| Like an old lady (anagram of ELIAN) | 35 |
| Like an old joke | 16 |
| Like an old hand | 16 |
| Like an old grate | 17 |
| Like an old Frankfurter | 23 |
| Like an old English coin worth 21 shillings | 43 |
| Like an old cuss | 16 |
| Like an old cliche | 18 |
| Like an old cigar | 17 |
| Like an old chestnut | 20 |
| Like an old bucket of song | 26 |
| Like an old bialy | 17 |
| Like an old bagel | 17 |
| Like an old auto | 16 |
| Like an old apple, maybe | 24 |
| Like an old apartment | 21 |
| Like an old Andean empire | 25 |
| Like an oily mitt | 17 |
| Like an officious intermeddler | 30 |
| Like an offer that's under actual value | 43 |
| Like an off-pitch piano | 23 |
| Like an off-key football lineman? | 33 |
| Like an oeil-de-boeuf window | 28 |
| Like an oeil-de-boeuf | 21 |
| Like an ode | 11 |
| Like an oddball | 15 |
| Like an octopus's defense | 29 |
| Like an octopus' defense | 28 |
| Like an octogenarian | 20 |
| Like an obsessive mind | 22 |
| Like an obsessive collector | 27 |
| Like an oboe, but not a sax? | 28 |
| Like an oboe's tones | 24 |
| Like an oboe's sound | 24 |
| Like an oboe in sound | 22 |
| Like an oath | 12 |
| Like an oak leaf | 16 |
| Like an O. Henry ending | 23 |
| Like an NBA power forward | 25 |
| Like an NBA player | 18 |
| Like an NBA newlywed? | 21 |
| Like an N.C.O. | 14 |
| Like an N.B.A. center | 21 |
| Like an ivory-billed woodpecker | 31 |
| Like an itchy spot | 18 |
| Like an island | 14 |
| Like an irritated person's teeth? | 37 |
| Like an ironclad case | 21 |
| Like an iron alloy | 18 |
| Like an Irish terrier, colorwise | 32 |
| Like an Irish bog | 17 |
| Like an iris part | 17 |
| Like an inveterate procrastinator | 33 |
| Like an intimate dinner | 23 |
| Like an interstate highway | 26 |
| Like an Interstate | 18 |
| Like an intense storm | 21 |
| Like an insult comic's material, often | 42 |
| Like an insufficient account | 28 |
| Like an insufferable, privileged sophomore who hates everyone ... and is melodramatic about it | 94 |
| Like an insufferable, privileged sophomore who hates everyone | 61 |
| Like an instant replay | 22 |
| Like an inspection | 18 |
| Like an insomniac's night | 29 |
| Like an insomniac | 17 |
| Like an insole | 14 |
| Like an insincere compliment | 28 |
| Like an inside-the-park home run | 32 |
| Like an inscribed pillar | 24 |
| Like an inscribed monument | 26 |