| MEMORIALDAY | Late-May observance, whose first word can follow each answer to a starred clue |
| YOGA | Word that can follow each answer to the starred clues |
| WHITEWATER | Canoeing challenge whose first word can precede the start and whose second word can precede the end of the answers to starred clues |
| NANOWRIMO | November observance whose name appears in this puzzle's theme entries |
| BLACKMONDAY | 1987 market crash, and this puzzle's title, whose first word can precede each word in the starred an |
| INVISIBLEHAND | Unseen market force, or a hint to what can follow each starred answer's first word and precede its last word |
| DOUBLETIME | Holiday pay rate, perhaps, and a hint to what can follow each word of each starred answer |
| WORLDLEADER | Summit attendee, and what the first word can be in each answer to a starred clue |
| MARKMYWORDS | "Remember what I said!" ... and a hint to what can follow each part of the answers to starred clues |
| STONEWALL | 1969 LGTBQ+ uprising site ... or any side of this grid, based on a word that can follow each starred answer? |
| LINE | Word that can follow each part of the answers to the six starred clues |
| CARD | Word that can follow each half of each shaded answer |
| BOX | Square that can follow each of the three words in each starred answer |
| BAR | Happy hour site, and word that can follow each last name in the answers to starred clues |
| MATE | Aussie pal, or what can follow each word in the answers to starred clues |
| JOINTHECLUB | "That's exactly how I feel" ... or what each starred clue's first word can do? |
| THELINE | Bettor's concern, which can follow each half of the answers to starred clues |
| FIRSTFAMILYBUYSISLAND | [... White House occupants make a Caribbean purchase] (Theme hint: What can follow each word of the bracketed clues' answers?) |
| MAN | Word that can follow each long answer |
| HEAD | What can follow each word in the five longest Across answers |
