| 100% | JONESES | 7 | Keep up with the ___ (try to attain what others have) |
| 50% | ENVY | 4 | Need to keep up with the Joneses |
| 48% | RUN | 3 | Try to keep up with a marathoner |
| 48% | DAT | 3 | Keeping up with the news helps you stay up-to-___e |
| 46% | WEED | 4 | Keep up with the plot |
| 46% | STOKE | 5 | What people had to do to keep the "Mauretania" running |
| 44% | TAKEASWING | 10 | Try to hit, or what one can do with the ends of 18-, 26- and 47-Across |
| 44% | HOMESTRETCH | 11 | Hint to what the other nine longest answers have in common |
| 44% | ETYMOLOGY | 9 | What the two words in each starred answer have in common with each other |
| 43% | NEWSJUNKIE | 10 | One who might keep up with the Times |
| 43% | DISPOSALS | 9 | Aids in keeping up with the daily grind? |
| 43% | STAYCURRENT | 11 | Keep up with what's new |
| 43% | TIME | 4 | With 63-Across, what (in abbreviated form) has been added to the long Down answers |
| 43% | ROPES | 5 | What newbies have to learn, with "the" |
| 42% | MEMES | 5 | They’re hard to keep up with on the Internet |
| 42% | SLANG | 5 | It’s hard to keep up with on the Internet |
| 42% | TILLYOULOVEME | 13 | Reba McEntire song with the lyric "I guess I can wait if that's what I have to do" |
| 42% | EYE | 3 | With 65-Across, what the last words of 18-, 35- and 56-Across are to each other |
| 42% | OUTER | 5 | With 39-Across, region beyond the Kármán line ... or a literal hint to what this puzzle has |
| 42% | LEAKED | 6 | What the CIA's Joshua Adam Schulte did with documents he had access to in March 2016 |
| 41% | LAGS | 4 | Doesn't keep up with other people |
| 41% | EMPATHY | 7 | The ability to feel what others feel |
| 41% | TOPS | 4 | With the giant letter formed by the black squares immediately above this answer, what the answers to the starred clues all literally have |
| 41% | SCARY | 5 | Keeping you up at night with your eyes wide open and the sheets pulled up to your chin, say |
| 41% | FISHHEADS | 9 | 1978 novelty song with the line "Eat them up! Yum!" ... and what both parts of the answers to starred clues can be |
| 40% | ANYMOMENT | 9 | "It's about to happen" ... or what each of the four other longest answers in this puzzle has? |
| 40% | STANDONONESHEAD | 15 | Try to see things the other way |
| 40% | REDUCE | 6 | What the enthusiastically environmentally conscious try to do with just about everything |
| 40% | RAP | 3 | What a suspect tries to beat, with "the" |
| 40% | ARMWRESTLE | 10 | Try to get the upper hand in competition? |