| 100% | LEFTHAND | 8 | Bill Gates and Barrack Obama write with this |
| 42% | DROPOUTS | 8 | Bill Gates and Matt Damon, with respect to Harvard |
| 39% | COLLEGEDROPOUTS | 15 | Bill Gates and Oprah Winfrey, famously, and a hint to some three-letter abbreviations in this puzzle |
| 36% | CEOS | 4 | Bill Gates and Steve Jobs |
| 34% | MICROSOFT | 9 | Bill Gates founded this company |
| 33% | CUNEIFORM | 9 | Writing with wedges and such |
| 32% | LEFTHAND | 8 | Non-southpaws may find it hard to write with this |
| 32% | LEOS | 4 | Bill Clinton and Barack Obama, astrologically |
| 31% | TEDTALKS | 8 | Bill Gates gave six of them between 2009 and 2015 |
| 31% | CHEDDAR | 7 | *Say Cheese!* with this "mac and cheese" cheese |
| 30% | PENS | 4 | Writing utensils with ballpoint and fountain varieties |
| 30% | AFC | 3 | Grp. with Bills and Chargers |
| 30% | PORTFOLIO | 9 | Bill Gates' financial planner likely has quite an impressive one of these |
| 29% | PICODEGALLO | 11 | Topping made with this puzzle's chopped and squeezed ingredients |
| 29% | HAM | 3 | Dr. Seuss wrote about Green Eggs and this |
| 29% | CROSSWORDPUZZLE | 15 | With 37- and 56-Across, what this is |
| 29% | COOKBOOK | 8 | This is filled with recipe lists and instructions |
| 29% | PEN | 3 | Writing utensil with "fountain" and "felt-tip" varieties |
| 29% | PEN | 3 | Writing instrument with felt-tip and fountain types |
| 29% | STYLUS | 6 | Writing implement used with touchscreens and electronic devices |
| 29% | TENS | 4 | Bills with splashes of red, orange and yellow |
| 29% | PENCIL | 6 | Wood and graphite to write with |
| 29% | PEACE | 5 | Tolstoy wrote about War and this |
| 29% | FIRSTLADY | 9 | Michelle Obama and Laura Bush were this |
| 29% | CONTRA | 6 | Konami arcade game with Bill and Lance |
| 29% | WES | 3 | Frequent collaborator with Jason, Tilda, and Bill |
| 29% | PREJUDICE | 9 | Jane Austen wrote about Pride and this |
| 29% | OTHER | 5 | Alternative to this and that, with "the" |
| 29% | OTHER | 5 | Partner for this and that, with "the" |
| 29% | BESS | 4 | Gershwin opera with Porgy and this character |