| Pioneer's rug material | 26 |
| Pioneer's slogan on the way west | 36 |
| Pioneer's transport | 23 |
| Pioneer's transportation | 28 |
| Pioneer's vehicle | 21 |
| Pioneer's wagon | 19 |
| Pioneer, as a trail | 19 |
| Pioneer, e.g. | 13 |
| Pioneer: abbr. | 14 |
| Pioneered | 9 |
| Pioneered, as a movement | 24 |
| Pioneering | 10 |
| Pioneering "hot" jazz guitarist | 41 |
| Pioneering 1740 novel subtitled "Virtue Rewarded" | 59 |
| Pioneering 1940's computer | 30 |
| Pioneering 1940s computer | 25 |
| Pioneering 1950 Isaac Asimov book | 33 |
| Pioneering 1982 film | 20 |
| Pioneering 1982 sci-fi film | 27 |
| Pioneering 35 mm. camera | 24 |
| Pioneering 50's news program | 32 |
| Pioneering 70's video game | 30 |
| Pioneering agriculturist Jethro | 31 |
| Pioneering anti-AIDS drug | 25 |
| Pioneering automaker | 20 |
| Pioneering beatboxer on "La Di Da Di" | 47 |
| Pioneering black comedian (whose signature line was "Oh, yeah!"), ___ Rogers | 86 |
| Pioneering black sportscaster | 29 |
| Pioneering blues singer Smith | 29 |
| Pioneering Boeing planes | 24 |
| Pioneering brand of decaf coffee | 32 |
| Pioneering Canadian physician, Sir William ___ | 46 |
| Pioneering cartoonist | 21 |
| Pioneering cell phone co. | 25 |
| Pioneering child care author | 28 |
| Pioneering Christian rockers | 28 |
| Pioneering collagist | 20 |
| Pioneering college football coach | 33 |
| Pioneering comedy film producer | 31 |
| Pioneering comic Bruce | 22 |
| Pioneering company behind "As Seen on TV" products | 60 |
| Pioneering company originally named Syzygy | 42 |
| Pioneering computer | 19 |
| Pioneering computer game | 24 |
| Pioneering computer of 1951 | 27 |
| Pioneering computer, for short | 30 |
| Pioneering conservationist | 26 |
| Pioneering D.J. Freed | 21 |
| Pioneering Dadaist | 18 |
| Pioneering deejay Freed | 23 |
| Pioneering DJ Freed | 19 |
| Pioneering dub reggae producer nicknamed "Scratch" | 60 |
| Pioneering Edward R. Murrow show of the '50s | 48 |
| Pioneering electrical engineer | 30 |
| Pioneering electrical engineer Nikola | 37 |
| Pioneering electronic calculators | 33 |
| Pioneering English Quaker | 25 |
| Pioneering film in stop-motion animation | 40 |
| Pioneering film of 1940 | 23 |
| Pioneering films | 16 |
| Pioneering Frank King comic strip featuring Walt and Skeezix | 60 |
| Pioneering French designer with her own fragrance | 49 |
| Pioneering game company | 23 |
| Pioneering game systems | 23 |
| Pioneering General Motors electric car | 38 |
| Pioneering geneticist | 21 |
| Pioneering German auto | 22 |
| Pioneering golf shoe brand | 26 |
| Pioneering heavy-metal band | 27 |
| Pioneering hip-hop group with the hit "Walk This Way" | 63 |
| Pioneering hybrid | 17 |
| Pioneering hypnotist | 20 |
| Pioneering Internet company | 27 |
| Pioneering ISP | 14 |
| Pioneering Italian sculptor | 27 |
| Pioneering jazz standard of 1917 | 32 |
| Pioneering late-night talker | 28 |
| Pioneering magician Tony | 24 |
| Pioneering map publisher William | 32 |
| Pioneering mathematician | 24 |
| Pioneering microcomputer | 24 |
| Pioneering musician in stereo ___ Light | 39 |
| Pioneering name in car batteries | 32 |
| Pioneering nü-metal band | 27 |
| Pioneering organizer | 20 |
| Pioneering pair preserver | 25 |
| Pioneering pilot Earhart | 24 |
| Pioneering Pittsburgh radio station | 35 |
| Pioneering pollster Roper | 25 |
| Pioneering programmer Lovelace | 30 |
| Pioneering puffed cereal | 24 |
| Pioneering pulp magazine | 24 |
| Pioneering puppeteer | 20 |
| Pioneering puppeteer Tony | 25 |
| Pioneering quantum theorist | 27 |
| Pioneering rap trio | 19 |
| Pioneering rap trio from Queens | 31 |
| Pioneering razor with a pivoting head | 37 |
| Pioneering reporter Rogers St. Johns | 36 |
| Pioneering Russian spacecraft series | 36 |