| 100% | PODCAST | 7 | NPR's "Planet Money" or "How I Built This" |
| 46% | LORDOFTHEFRIES | 14 | Or "How I Built My Fast-Food Empire"? |
| 40% | DOLLARSANDCENTS | 15 | Money ... or a hint to how six crossings in this puzzle are to be represented, superimposing one letter over another |
| 38% | TABBY | 5 | Certain lap warmer, or how one might playfully describe this puzzle's longest answers |
| 38% | GELT | 4 | Chocolate money won or lost in this puzzle's game |
| 37% | CHECKALL | 8 | With 39-Down, fulfill requirements ... or how to fill four of this puzzle's squares? |
| 37% | INME | 4 | How I might want you to believe or trust |
| 36% | DONTLOOKATME | 12 | “I had nothing to do with it!” . . . or how to make sense of twelve of this puzzle’s clues |
| 35% | DOTHEMATH | 9 | "Figure it out!" … or how to arrive at this puzzle's solution, using the answers to italicized clues |
| 35% | ONABET | 6 | How money may be won or lost |
| 35% | OKSO | 4 | "And this affects me ... how?" |
| 35% | ENDLESSLY | 9 | On and on ... or how to read 18-, 27-, 37- and 51-Across to understand this puzzle's theme? |
| 35% | AGAINSTALLODDS | 14 | How an extreme underdog wins ... or this puzzle? |
| 35% | MORTGAGE | 8 | Money borrowed to buy a house or building |
| 35% | SOO | 3 | "And this pertains to me ... how?" |
| 34% | INARO | 5 | Indirectly ... or how some of this puzzle's answers should be entered? |
| 34% | ANYADVICE | 9 | "Want to tell me how you'd handle this?" |
| 33% | BET | 3 | You either lose or win money with this |
| 33% | WHATDOYOUMEANWE | 15 | "Wait, how am I getting dragged into this?" |
| 33% | INANE | 5 | Foolish ... or, when read as three words, how this puzzle's other four "foolish" answers are arranged |
| 33% | FRUITLESSLY | 11 | How I hope you don't try to solve most contest crosswords...except this puzzle |
| 33% | YET | 3 | "...or better ___, let me show you how it's done." |
| 32% | ATOZ | 4 | The works ... or how each set of circled letters in this puzzle is arranged |
| 32% | INLIVINGCOLOR | 13 | 1990s sketch comedy show, or how you'll see the creatures in this puzzle |
| 32% | INSIDEOUT | 9 | Thoroughly … or how to read the four Across answers with parentheses in this puzzle |
| 32% | PROTIP | 6 | "Let me tell you, this is how to do it" |
| 31% | TAX | 3 | I.R.S. money |
| 31% | BUDGETCUT | 9 | "Sittin' in the Sun (Countin' My Money)" or "Can't Buy Me Love"? |
| 31% | MICROLOANS | 10 | Money to start small businesses ... or a hint to five squares in this puzzle |
| 31% | ROLL | 4 | "That's how I —" |