| "26 Miles" island | 27 |
| "25. I'm supposed to come up with 25 random things?Sorry, I think that's all I've ___" | 108 |
| "25 words or less" event | 34 |
| "25 or 6 to 4" singer Peter | 37 |
| "25 or 6 to 4" band | 29 |
| "24. The first crossword I ever wrote I sold to the ___.It ran on 8/7/1996" | 85 |
| "24" superagent Jack | 30 |
| "24" superagent | 25 |
| "24" star Sutherland | 30 |
| "24" protagonist Jack | 31 |
| "24" hero Jack | 24 |
| "24" agent Jack | 25 |
| "24" actress Raver | 28 |
| "24" actress Cuthbert | 31 |
| "24 Hours" writer Greg | 32 |
| "24 Hours From Tulsa" singer Gene | 43 |
| "23. I think Bill ___ was an inspired comic." | 55 |
| "23" Blonde ___ | 25 |
| "23 ___": Var. | 24 |
| "227" role | 20 |
| "22. I'm convinced I'm going to lose all my ___" | 66 |
| "22" is one | 21 |
| "2112" trio | 21 |
| "21. I have a tough time listening to ___ in front of women ('Ready To Die' is too misogynist)" | 113 |
| "21" singer | 21 |
| "21" school | 21 |
| "21" sch. | 19 |
| "21" artist | 21 |
| "21" and "19" singer | 40 |
| "21 ___" (2003 Sean Penn film) | 40 |
| "21 ___" | 18 |
| "21 Grams" star | 25 |
| "2016: Obama's America" director/producer | 55 |
| "2012" actress Amanda | 31 |
| "2010: Odyssey Two" computer | 38 |
| "2001: ___ Odyssey" | 29 |
| "2001: A Space Odyssey" studio | 40 |
| "2001: A Space Odyssey" star | 38 |
| "2001: A Space Odyssey" mainframe | 43 |
| "2001: A Space Odyssey" computer | 42 |
| "2001: A Space Odyssey" author | 40 |
| "2001..." studio | 26 |
| "2001" studio | 23 |
| "2001" stone | 22 |
| "2001" processor | 26 |
| "2001" malefactor | 27 |
| "2001" mainframe | 26 |
| "2001" extras | 23 |
| "2001" computer | 25 |
| "2001" characters? | 28 |
| "2001" characters | 27 |
| "2001" and "2010" studio | 44 |
| "2001 . . ." talker | 29 |
| "2001 . . ." role | 27 |
| "2001 . . ." distributor | 34 |
| "2001 . . ." computer | 31 |
| "2001 . . ." astronaut | 32 |
| "20000 lieues sous les ___" (Jules Verne book) | 56 |
| "200 ___" (1971 Frank Zappa movie and album) | 54 |
| "20/20" reporter John | 31 |
| "20/20" network | 25 |
| "20/20" journalist Lynn | 33 |
| "20/20" creator Arledge | 33 |
| "20/20" creator | 25 |
| "20/20" airer | 23 |
| "20. My all-time favorite football player is ___" | 59 |
| "20,000 Leagues" mate ___ Land | 40 |
| "20,000 Leagues" harpooner ___ Land | 45 |
| "20,000 Leagues" captain | 34 |
| "20,000 Leagues ___ the Sea" | 38 |
| "20,000 Leagues Under the Sea" writer | 47 |
| "20,000 Leagues Under the Sea" actor, 1954 | 52 |
| "20 Questions" category / Layer | 41 |
| "20 Questions" category | 33 |
| "20 Hrs., 40 Min." author, 1928 | 41 |
| "2. I've never been more drunk than the New Years Eve night 1999 when I polished off three bottles of ___" | 120 |
| "2, 4, 6, 8 — who do we appreciate?," e.g. | 56 |
| "2, 4, 6, 8 - Who do we appreciate?," e.g. | 52 |
| "2, 3, 4" lead-in | 27 |
| "2 ___ 2 Furious" (2003 movie) | 40 |
| "2 ND" | 16 |
| "2 Minute Drill" channel | 34 |
| "2 Minute Drill" cable channel | 40 |
| "2 in 1" shampoo and conditioner with FDA approval? | 61 |
| "2 Fast 2 Furious" co-star Gibson | 43 |
| "2 Fast 2 Furious" actress Mendes | 43 |
| "2 Broke Girls" network | 33 |
| "2 Broke Girls" costar Dennings | 41 |
| "2 Broke Girls" co-star Dennings | 42 |
| "2 Broke Girls" channel | 33 |
| "2 Broke Girls" and "30 Rock" | 49 |
| "2 Broke Girls" actress Dennings | 42 |
| "1st and 10" airer | 28 |
| "1st & Ten" star | 30 |
| "1985" novelist | 25 |
| "1984" worker | 23 |
| "1984" utterances | 27 |
| "1984" superstate dominated by Neo-Bolshevism | 55 |
| "1984" superstate | 27 |
| "1984" superpower | 27 |