| '33 Chicago World's Fair puppeteer | 42 |
| '32 Flavors' singer Davis | 33 |
| '30s-'50s British Labour Party leader | 45 |
| '30s-'40s Kildare portrayer | 35 |
| '30s-'40s film dog | 26 |
| '30s-'40s Dr. Kildare portrayer | 39 |
| '30s-'40s country star Roy | 34 |
| '30s-'40s actress D'Orsay | 37 |
| '30s Yankee star | 20 |
| '30s world chess champion Max | 33 |
| '30s VP John ___ Garner | 27 |
| '30s veep John __ Garner | 28 |
| '30s V.P. John __ Garner | 28 |
| '30s show tune that became a 1960 Dion and the Belmonts hit | 63 |
| '30s power proj. | 20 |
| '30s pitching great known for his malapropisms | 50 |
| '30s nightclub employee | 27 |
| '30s migrant worker | 23 |
| '30s migrant | 16 |
| '30s home run king | 22 |
| '30s heavyweight champ Max | 30 |
| '30s heavyweight champ | 26 |
| '30s Great Plains blight | 28 |
| '30s Giant slugger | 22 |
| '30s First Mother | 21 |
| '30s film megastar | 22 |
| '30s entertainer Ivor | 25 |
| '30s employer of the Marxes | 31 |
| '30s dance that was all the rage | 36 |
| '30s dance named after an aviator | 37 |
| '30s dance | 14 |
| '30s civil war site | 23 |
| '30s chanteuse Edith | 24 |
| '30s Chan portrayer | 23 |
| '30s candidate Landon et al. | 32 |
| '30s boxing champ | 21 |
| '30s bomber | 15 |
| '30s bandleader Jones | 25 |
| '30s Army bomber | 20 |
| '30s and '40s pitcher Newsom | 36 |
| '30s actress Pitts | 22 |
| '30s action-film star | 25 |
| '300' city | 18 |
| '30 Rock' star | 22 |
| '30 Rock' role | 22 |
| '30 Rock' network | 25 |
| '30 Rock' cast member | 29 |
| '30 days --...' | 23 |
| '25 Chaplin film | 20 |
| '24' actress Cuthbert | 29 |
| '24 Caprices for Solo Violin' composer | 46 |
| '23 --!' | 16 |
| '21 Chaplin film | 20 |
| '20s-'30s skating gold medalist | 39 |
| '20s-'30s Flying Cloud, e.g. | 36 |
| '20s White House nickname | 29 |
| '20s tennis great Lacoste | 29 |
| '20s tennis champ Lacoste | 29 |
| '20s suits | 14 |
| '20s style | 14 |
| '20s set designer for MGM | 29 |
| '20s Russian leader | 23 |
| '20s outerwear | 18 |
| '20s Hollywood idol | 23 |
| '20s heavyweight champ | 26 |
| '20s Ford | 13 |
| '20s fad just before the crossword craze | 44 |
| '20s entertainment | 22 |
| '20s English Channel swimmer | 32 |
| '20s dispenser | 18 |
| '20s DC scandal | 19 |
| '20s cars | 13 |
| '20s car | 12 |
| '20s bathtub filler | 23 |
| '20s barroom | 16 |
| '20s autos | 14 |
| '20s auto | 13 |
| '20s assembly-line Ford | 27 |
| '20s artist | 15 |
| '20s art style | 18 |
| '20s anarchist | 18 |
| '2012' subject | 22 |
| '2001: A Space Odyssey' author | 38 |
| '2001' villain | 22 |
| '2001' name | 19 |
| '2001' computer | 23 |
| '2001' co-star Keir | 27 |
| '2001' author | 21 |
| '20/20' airer | 21 |
| '20,000 Leagues Under the Sea' author | 45 |
| '20 Questions' category | 31 |
| '2%' drink | 18 |
| '2 Broke Girls' role | 28 |
| '2 Broke Girls' airer | 29 |
| '1984' state | 20 |
| '1984' laborer | 22 |
| '1984' author | 21 |
| '18 or older' provision | 31 |
| '14s in '14, e.g. | 25 |
| '1492' director Ridley | 30 |