| Oldest printed song for Yuletide | 32 |
| Oldest signer of the Declaration of Independence | 48 |
| Oldest synagogue in the U.S., in Newport, R.I. | 46 |
| Oldest technological univ. in America | 37 |
| Oldest U.S. civil liberties org. | 32 |
| Oldest U.S. department store chain | 34 |
| Oldest U.S. settlement west of the Rockies | 42 |
| Oldest winner of the Indianapolis 500 at 47 | 43 |
| Oldie introduced by Ethel Waters: 1924 | 38 |
| Oldie recorded by Midler in '72 | 35 |
| Oldie with "all alone and feeling blue" | 49 |
| Oldie with a star character named Stone | 39 |
| Oldman's "JFK" role | 33 |
| Olds compacts introduced in 1998 | 32 |
| Olds models of the '80s and '90s | 40 |
| Olds models of the '80s-'90s | 36 |
| Oldsmobile model of the '70s and '80s | 45 |
| Oldsmobile's last model produced | 36 |
| Olduvai ___ (archaeological site in Tanzania) | 45 |
| Olduvai ___ (site of many early hominid fossils) | 48 |
| Ole of "Hellzapoppin'" | 36 |
| Olfactory reward for leading a good life? | 41 |
| Olga's rival in the 70's | 32 |
| Olga, Masha and Irina's creator | 35 |
| Olin in "Romeo is Bleeding" | 37 |
| Olin of ''Chocolat'' | 36 |
| Olin of "Enemies, a Love Story" | 41 |
| Olin of "Hollywood Homicide," 2003 | 44 |
| Olin's "Mr. Jones" co-star, 1993 | 46 |
| Oliva's "I love you" | 34 |
| Olive and family from "Popeye" | 40 |
| Olive and family, from "Popeye" | 41 |
| Olive color used in some cosmetics? | 35 |
| Olive of "Thimble Theatre" | 36 |
| Olive Oyl, in Popeye's words | 32 |
| Olive that goes with a little salt? | 35 |
| Olive ___ (Popeye's sweetie) | 32 |
| Olive ___, often seized by Bluto | 32 |
| Oliver Cromwell tried to melt them down | 39 |
| Oliver Hazard Perry victory site | 32 |
| Oliver Mellors, to Lady Chatterley | 34 |
| Oliver North's alma mater: Abbr. | 36 |
| Oliver of ''The West Wing'' | 43 |
| Oliver of "Flatliners" | 32 |
| Oliver of "Frost/Nixon" | 33 |
| Oliver of "Lake Placid" | 33 |
| Oliver of "The West Wing" | 35 |
| Oliver of "X-Men: First Class" | 40 |
| Oliver Stone film about the 37th president | 42 |
| Oliver Stone's Oscar winner 1986 | 36 |
| Oliver who directed "W." | 34 |
| Oliver ___, English novelist: 1873–1961 | 46 |
| Oliver's "As You Like It" love | 44 |
| Oliver's leavings = Craig's _____ | 41 |
| Oliver's love in "As You Like It" | 47 |
| Oliver's wife on "Green Acres" | 44 |
| Olivia de Havilland film of 1949 | 32 |
| Olivia de Havilland's birthplace | 36 |
| Olivia in "Twelfth Night," e.g. | 41 |
| Olivia Newton-John film of '80 | 34 |
| Olivia Newton-John film with a few Top 40 hits | 46 |
| Olivia Newton-John's grandfather | 36 |
| Olivia of "The Changeup" | 34 |
| Olivia of "The Wonder Years" | 38 |
| Olivia ___ of "The Wonder Years" | 42 |
| Olivia's last name on "Scandal" | 45 |
| Olivia's love in "Twelfth Night" | 46 |
| Olivier's "Rebecca" costar | 40 |
| Ollie North's '80s "affair" | 45 |
| Ollie's buddy, in early kidvid | 34 |
| Ollie's partner as a tiller of the soil? | 44 |
| Ollie's partner in old comedy | 33 |
| Ollie's partner in slapstick | 32 |
| Olly Olly ____ Free : '78 Hepburn film | 45 |
| Olmos's "... Galactica" role | 42 |
| Olmos's "Battlestar Galactica" role | 49 |
| Olsen of "Hellzapoppin'" | 38 |
| Olsen of "Hellzapoppin" | 33 |
| Olympian and Peter Pan portrayer Cathy | 38 |
| Olympian famed for sticking her landing | 39 |
| Olympian Griffith Joyner, familiarly | 36 |
| Olympian known for his fighting ability | 39 |
| Olympian Nurmi known as the Flying Finn | 39 |
| Olympian on 2004 and 2012 Wheaties boxes | 40 |
| Olympian once imprisoned in a jar | 33 |
| Olympian's achievement, perhaps | 35 |
| Olympian's ultimate achievement | 35 |
| Olympians in red, white and blue | 32 |
| Olympians who compete on their backs | 36 |
| Olympic "Flying Finn" Paavo | 37 |
| Olympic abbr. for Sydney's land | 35 |
| Olympic boxing gold medalist of 1964 | 36 |
| Olympic curling gold medalist Law | 33 |
| Olympic decathlon gold medalist ___ Eaton | 41 |
| Olympic event dating back to ancient Greece | 43 |
| Olympic event with electrified equipment | 40 |
| Olympic event won by Marcel Fischer in 2004 | 43 |
| Olympic event won by Matteo Tagliariol in 2008 | 46 |
| Olympic female gymnast, typically | 33 |
| Olympic figure skating champ Dorothy | 36 |