| ''Paper Roses'' singer Marie | 44 |
| ''Paper Roses'' singer Bryant | 45 |
| ''Paper or plastic'' item | 41 |
| ''Paper Moon'' surname | 38 |
| ''Paper Moon'' stars | 36 |
| ''Paper Moon'' star | 35 |
| ''Paper Moon'' Oscar winner | 43 |
| ''Paper Moon'' actor or actress | 47 |
| ''Paper Lion'' star | 35 |
| ''Papa Loves Mambo'' singer | 43 |
| ''Papa Bear'' | 29 |
| ''Pants on fire'' guy | 37 |
| ''Panic in the Streets'' director Kazan | 55 |
| ''Pale'' brews | 30 |
| ''Pale Rider,'' e.g. | 36 |
| ''Pal Joey'' playwright | 39 |
| ''Pal Joey'' author | 35 |
| ''Paint Your Wagon'' composer | 45 |
| ''Pah-pah'' preceder | 36 |
| ''Paganini'' composer | 37 |
| ''Paganini'' actor | 34 |
| ''P.S.___'' ('90s detective series) | 55 |
| ''Oy!'' | 23 |
| ''Oxford Blues'' heroine | 40 |
| ''Owner of a Lonely Heart'' group | 49 |
| ''Over ___'' | 28 |
| ''Over There'' penner | 37 |
| ''Over There'' conflict, briefly | 48 |
| ''Over There'' composer | 39 |
| ''Over the Rainbow'' composer | 45 |
| ''Over the hill'' in the military | 49 |
| ''Over my dead body!'' | 38 |
| ''Over here'' | 29 |
| ''Over here!'' | 30 |
| ''Over easy'' order | 35 |
| ''Outta sight!'' | 32 |
| ''Outland'' character | 37 |
| ''Outer'' word form | 35 |
| ''Out, dagnabbit!'' | 35 |
| ''Out on a Limb'' singer Marie | 46 |
| ''Out of the way!'' | 35 |
| ''Out of the Silent Planet'' author | 51 |
| ''Out of my way!'' | 34 |
| ''Out of here!'' | 32 |
| ''Out of Africa'' writer Dinesen | 48 |
| ''Out of Africa'' setting | 41 |
| ''Out of Africa'' pseudonym Dinesen | 51 |
| ''Out of Africa'' novelist Dinesen | 50 |
| ''Out of Africa'' author Dinesen | 48 |
| ''Out of Africa'' author | 40 |
| ''Our ___ Will Come'' | 37 |
| ''Our Town'' girl | 33 |
| ''Our Town'' author Wilder | 42 |
| ''Our Miss Brooks'' student Walter | 50 |
| ''Our Miss Brooks'' star | 40 |
| ''Our Miss Brooks'' actress | 43 |
| ''Our Miss Brooks'' | 35 |
| ''Our Man in Havana'' author | 44 |
| ''Our Man Flint'' star | 38 |
| ''Our Gang'' dog | 32 |
| ''Our Father'' | 30 |
| ''Oui'' opposite | 32 |
| ''Oui'' and ''si'' | 50 |
| ''Otherwise, you'll regret it!'' | 52 |
| ''Otherwise ...'' | 33 |
| ''Otherwise . . .'' | 35 |
| ''Other'' category, briefly | 43 |
| ''Othello'' villain | 35 |
| ''Othello'' provocateur | 39 |
| ''Othello'' evildoer | 36 |
| ''Othello'' antagonist | 38 |
| ''Otello'', for one | 35 |
| ''Otello'' highlight | 36 |
| ''Otello'' composer | 35 |
| ''Orphee'' painter | 34 |
| ''Orinoco Flow'' singer | 39 |
| ''Ordinary People'' actress | 43 |
| ''Orange'' attachment | 37 |
| ''Or'' partner | 30 |
| ''Or ___!'' (veiled threat) | 43 |
| ''Or ___!'' | 27 |
| ''Or ___ thought'' | 34 |
| ''Oppression and Liberty'' author Simone | 56 |
| ''Open, Sesame'' man | 36 |
| ''Open, Sesame!'' speaker | 41 |
| ''Open ___ midnight'' | 37 |
| ''Open wide'' word | 34 |
| ''Open 10 __ 6'' | 32 |
| ''Oops!'' | 25 |
| ''Oops! . . . I Did It Again'' singer | 53 |
| ''Oohs'' partners | 33 |
| ''Oohs'' companion | 34 |
| ''Only ___'' | 28 |
| ''Only When I Laugh'' actor James | 49 |
| ''Only the Lonely'' actress Maureen | 51 |
| ''Only the Good ___ Young'' | 43 |
| ''One-horse open sleigh'' follower | 50 |
| ''One,'' to Rocky | 33 |
| ''One ___ land'' (Longfellow) | 45 |
| ''One True Thing'' writer Quindlen | 50 |