| Oscar-nominated actor with the given name Aristotelis | 53 |
| Oscar-nominated actress for "Enemies, A Love Story" | 61 |
| Oscar-nominated actress for "Leaving Las Vegas" | 57 |
| Oscar-nominated film featuring a dentist-turned-bounty hunter | 61 |
| Oscar-nominated role for Anthony Hopkins in "Amistad" | 63 |
| Oscar-nominated role for Dustin between Benjamin and Lenny | 58 |
| Oscar-nominated song from "Crouching Tiger, Hidden Dragon" | 68 |
| Oscar-winning "Casablanca" co-screenwriter Julius or Philip | 69 |
| Oscar-winning "Titanic" score composer James | 54 |
| Oscar-winning "Titanic" song by Celine Dion | 53 |
| Oscar-winning actor for "Little Miss Sunshine" | 56 |
| Oscar-winning actor who played Napoleon, Mussolini and W. C. Fields | 67 |
| Oscar-winning actor whose name is Italian for "fishes" | 64 |
| Oscar-winning actress for "The Great Lie," 1941 | 57 |
| Oscar-winning actress in "Melvin and Howard" | 54 |
| Oscar-winning actress in "Mighty Aphrodite" | 53 |
| Oscar-winning actress of ''Two Women'' | 54 |
| Oscar-winning director of "The Departed," 2006 | 56 |
| Oscar-winning director of "The Silence of the Lambs" | 62 |
| Oscar-winning foreign language film based on a Fugard novel | 59 |
| Oscar-winning portrayer of Police Chief Bill Gillespie, 1967 | 60 |
| Oscar-winning role for Cate Blanchett in "The Aviator" | 64 |
| Oscar-winning role for Holly in "The Piano" | 53 |
| Oscar-winning screenwriter for "The Social Network" | 61 |
| Oscar-winning song from "A Hole in the Head" | 54 |
| Oscar-winning song from "Captain Carey, U.S.A." | 57 |
| Ossie Davis role in ''Do The Right Thing'' | 58 |
| Othello's supposed rival for Desdemona's affection | 58 |
| Out of one's mind, in a way, with "up" | 52 |
| Outcome of the coin toss, or first team to score a touchdown, e.g. | 66 |
| Outdoor chore for author, singer, showman and President | 55 |
| Outdoor establishment that originated in southern Germany | 57 |
| Outdoor meals with hamburgers or hot dogs, say, in brief | 56 |
| Outfield "I just want to ___ your love tonight" | 57 |
| Outfield mate of Scooter, of the 40's-50's Yankees | 58 |
| Outfield wall that's unusually close to home plate | 54 |
| Outfielder inducted into the Baseball Hall of Fame in 1987 | 58 |
| Outfielder Minnie who played professionally in seven decades | 60 |
| Outfielder Moisés whom Steve Bartman famously interfered with | 64 |
| Outfielder Ricky who won two World Series rings with the Yankees | 64 |
| Outfielder who challenged baseball's reserve clause | 55 |
| Outfielder who had a single-season record 262 hits in 2004 | 58 |
| Outfielder who was a member of baseball's All-Century Team | 62 |
| OutKast album that rated #1 on Metacritic's Top Albums of 2000 | 66 |
| OutKast hit whence "shake it like a Polaroid picture" | 63 |
| Outlaw Belle who is said to have harbored Jesse James | 53 |
| Overcoming stiltedness, as with introductions in a group | 56 |
| Overconfident sexists wearing sunglasses indoors, for short | 59 |
| Overly bold member of the "Little Women" family? | 58 |
| Overpopulate part of Colorado, Utah, Arizona, and New Mexico? | 61 |
| Overpromotion of a Stephenie Meyers fantasy novel series? | 57 |
| Owen Wilson's "Midnight in Paris" role | 52 |
| Owen ___, rebel in Shakespeare's "King Henry IV" | 62 |
| Owner of Martini & Rossi, Dewar's and Grey Goose | 56 |
| Oxymoronic movie title, ''True ___'' | 52 |
| Ozzy's "sail across the ocean," perhaps (Abbr.) | 61 |