On the Up and Up NYT: Why This Classic Idiom Keeps Triping Up Crossword Fans

On the Up and Up NYT: Why This Classic Idiom Keeps Triping Up Crossword Fans

You're staring at your phone, the grid is nearly full, and there it is. A five or six-letter gap mocking you. The clue says "Honest" or maybe "Legit," and you're thinking about that specific phrase: on the up and up nyt. If you play the New York Times Crossword or the Spelling Bee, you know that the "Gray Lady" has a peculiar obsession with idioms that feel like they belong in a 1940s noir film. It’s one of those phrases that everyone understands but nobody can quite explain why it exists.

Honestly, it's a bit weird.

Most people use "on the up and up" to describe a business deal that isn't a scam. It’s clean. It’s transparent. But in the world of the NYT Crossword, edited for years by Will Shortz and now navigated by a rotating cast of brilliant constructors, this phrase is a staple because of its vowel-heavy structure. In the construction of a puzzle, vowels are gold. Words like "AREA," "ERIE," and "ALOE" are overused, but "UP AND UP" is a gift to a designer trying to bridge a difficult corner.

The Linguistic Roots of Being Legit

Where did this even come from? It sounds like something a street hustler would say while trying to prove he’s not selling you a fake watch. Linguists generally trace the origins back to the late 19th century. Initially, "on the up" just meant improving or rising, like a stock price or a person's health.

By the time it reached the 20th century, the repetition—the "up and up"—added a layer of emphasis. It became about more than just rising; it was about being out in the open. If you’re "up," you aren’t hidden in the shadows or under the table.

Interestingly, the NYT archives show the phrase appearing in various contexts over the decades. It’s appeared in everything from political reporting to sports commentary. When a team is "on the up and up," they aren't just winning; they are doing it without a whiff of scandal. It’s a phrase that carries the weight of integrity.

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Why the NYT Crossword Loves This Phrase

If you are hunting for on the up and up nyt clues, you have likely noticed a pattern. The NYT Crossword is notorious for "misdirection." A clue might be as simple as "Aboveboard" or as tricky as "Like a square deal."

The reason it appears so often is purely structural. Look at the letters: U-P-A-N-D-U-P.

You’ve got two Us. You’ve got a P. You’ve got the common "AND" bridge. This is a constructor’s dream. When Joel Fagliano or Robyn Weintraub is building a grid, they need "connectors." The phrase "up and up" provides a perfect vertical or horizontal anchor that allows for flexible crossing words.

Let's talk about the Friday and Saturday puzzles. These are the beasts. In a Saturday NYT puzzle, "on the up and up" won't be clued directly. You won’t get "Honest." You’ll get something like "Not smelling fishy, perhaps." That’s the NYT style—it tests your ability to link a colloquialism to a vague descriptor.

Common Misconceptions About the Phrase

People often confuse "on the up and up" with "on the upswing." They aren't the same.

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  • On the upswing: Things are getting better. Your bank account is growing. The economy is recovering.
  • On the up and up: Things are legal and moral. No one is getting cheated.

There is also a weird British variation where "on the up" is more common than the double "up and up." If you're solving a cryptic crossword from the UK, you might see it differently. But for the NYT, the Americanized double-up is the standard.

Sometimes, solvers get stuck because they think the answer should be "LEVEL." "Is this deal on the level?" That’s another classic NYT crossword filler. "LEVEL" and "UPANDUP" often fight for the same space in a solver’s brain. The trick is looking at the letter count. Five letters? Probably LEVEL. Seven or more? You’re looking at some variation of the "up and up."

The Evolution of NYT Clueing

In the 1970s and 80s, the clues were very literal. If the answer was "ON THE UP AND UP," the clue might have been "Straightforward."

Today, the NYT has moved toward "New Wave" clueing. They want you to smile when you figure it out. They want the "Aha!" moment. A 2024 puzzle clued a similar phrase as "Like a handshake deal in a movie where the guy isn't a villain." It’s conversational. It’s meta.

This change reflects a broader shift in how the New York Times approaches language. They are no longer just the arbiter of formal English; they are the curators of how we actually talk. By including phrases like on the up and up nyt, they acknowledge that idioms are the lifeblood of American English.

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How to Solve These Clues Faster

If you're tired of being stumped, you need to build a mental map of "Integrity Synonyms." The NYT has a "bucket" of words they use for this.

  1. ABOVEBOARD: This is the big one. If you see this in a clue, think "up and up" immediately.
  2. KOSHER: Often used when the puzzle wants to be a bit more informal.
  3. SQUARE: Think "a square deal."
  4. LEGAL: Too simple for a Saturday, but common on Mondays.
  5. HONEST: The baseline.

Wait, there's another trick. Look at the "Wordplay." If the clue has a question mark at the end, like "Rising twice?," it’s almost certainly a play on "UP AND UP." The question mark is the international symbol for "I am being cheeky" in crossword land.

The Cultural Impact of the NYT Games

We have to acknowledge that "The Crossword" isn't just a game anymore; it's a culture. With the rise of the NYT Games app, millions of people are chasing "The Streak." When a phrase like on the up and up nyt appears, it triggers a collective search. Google Trends often spikes for these specific idioms at 10:01 PM ET—the exact moment the new puzzle drops on weekdays.

It’s a shared struggle. You aren't just solving a puzzle; you’re participating in a linguistic ritual. The Spelling Bee also uses "UP" and "AND" frequently, though it rarely allows for full multi-word idioms. Still, the DNA of the NYT's word choice is consistent across all their platforms. They love words that feel familiar but are just slightly out of reach when you’re under pressure.

Actionable Insights for Daily Solvers

If you want to master the NYT Crossword and never be baffled by "on the up and up" again, change how you scan the grid. Stop looking for the "right" word and start looking for the "structural" word.

  • Check the vowels first: If you have a U and an A, "UP AND UP" is a high-probability candidate.
  • Identify the era: If the clue feels like it was written by a guy in a fedora (e.g., "A straight-shooting fella"), look for mid-century idioms.
  • Don't fear the multi-word answer: Modern NYT puzzles are famous for "stacks." This is where three or four long phrases are stacked on top of each other. "ON THE UP AND UP" is a perfect "stacker" because it provides common letters for the vertical words to pass through.
  • Use the "Check Word" tool sparingly: If you're playing digitally, it's tempting to hit check. Don't. If you're stuck on "on the up and up," walk away for ten minutes. The brain processes idioms better when it’s not staring directly at them.

The next time you see a clue about honesty or transparency, and the letters don't seem to fit "TRUTH" or "FACTS," remember the old-school charm of the on the up and up nyt. It’s a classic for a reason. It bridges the gap between the formal English of the past and the casual slang of the present, making it the perfect inhabitant of the world’s most famous crossword grid.

Keep your eyes on the grid and your mind open to the weird, repetitive, and wonderful idioms that make the New York Times puzzles a daily obsession. Whether you're a "Monday only" player or a "Saturday survivor," understanding these linguistic quirks is what separates the novices from the pros. Next time "Aboveboard" appears, you'll be ready.