| Old-school "That's totally wrong!" | 48 |
| Old-school "Yeah, right!" | 35 |
| Old-school dancehall cat ___ Tea | 32 |
| Old-school fastener at the roller disco | 39 |
| Old-school hardcore rappers, for short | 38 |
| Old-school maxim hater's cry | 32 |
| Old-school online chat option, briefly | 38 |
| Old-school player still at it (Abbr.) | 37 |
| Old-school word meaning "For shame!" | 46 |
| Old-style ''Bummer!'' | 37 |
| Old-style ''Scram!'' | 36 |
| Old-style ''Wow!'' | 34 |
| Old-style ''Yikes!'' | 36 |
| Old-style "For shame!" | 32 |
| Old-style "Listen up!" | 32 |
| Old-style computer monitor, for short | 37 |
| Old-style kitchen washing receptacle | 36 |
| Old-time actress Murray and others | 34 |
| Old-time actress Rich and others | 32 |
| Old-time actress Talbot or Naldi | 32 |
| Old-time actresses Allgood and Haden | 36 |
| Old-time actresses Markey and Bennett | 37 |
| Old-time alternative to ankle chains | 36 |
| Old-time Norwegian skating sensation | 36 |
| Old-time politician's pet bird? | 35 |
| Old-time songwriters' locale | 32 |
| Old-time tear-jerker, "___ Lynne" | 43 |
| Old-time worker in a freight yard | 33 |
| Old-timers, with "the" | 32 |
| Old-timey "Screw that" | 32 |
| Old-timey bicycle with the huge front wheel | 43 |
| Old-timey insult from the grandstands | 37 |
| Old-timey sailing ship with three masts | 39 |
| Olde ___ (historic area, quaintly) | 34 |
| Older brother of designers Vasco and Rodolfo | 44 |
| Older brother of Michael Jackson | 32 |
| Older cousin of "Cool!" | 33 |
| Older woman's plaything, in slang | 37 |
| Older woman's young lover, facetiously | 42 |
| Oldest "Brady Bunch" boy | 34 |
| Oldest "The Brady Bunch" sister | 41 |
| Oldest animal-safety org. in the U.S. | 37 |
| Oldest basketball tourney in the U.S. | 37 |
| Oldest Best Actress nominee (2012) | 34 |
| Oldest Best Actress Oscar winner | 32 |
| Oldest capital city in the United States | 40 |
| Oldest continuous democracy in Central America | 46 |
| Oldest driver to win the Indianapolis 500 | 41 |
| Oldest driver to win the Indy 500 | 33 |
| Oldest feminine org. in the U.S. | 32 |
| Oldest golfer to win the U.S. Open | 34 |
| Oldest independent country in Europe | 36 |
| Oldest kid on "Family Guy" | 36 |
| Oldest living thing in Middle Earth | 35 |
| Oldest of a trio of comedic brothers | 36 |
| Oldest of the "Animaniacs" siblings | 45 |
| Oldest of the "Little Women" | 38 |
| Oldest of the Rice Krispies brothers | 36 |
| Oldest permanent settlement in Ohio | 35 |
| 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 |