1985 "Hangman" launch advertisement for Tommy Hilfiger

This billboard doesn’t shout a brand name at you. It makes you work for it. At first glance you see a giant fill‑in‑the‑blank puzzle floating above Times Square traffic, daring passersby to prove how much they know about American menswear designers. Only after your brain starts guessing the missing letters do you notice the tiny colored flag in the corner. That “aha” moment is the entire ad.

How the puzzle hooks your brain

The board lists “The 4 great American designers for men” with their names turned into crossword-style blanks. Three are famous enough that you can mentally fill them in. The fourth line is harder, paired with a small red‑white‑blue flag and the line: “This is the logo of the least known of the four.” No big headline, no bragging copy—just a public quiz that instantly tells the brand how recognized that flag really is.

Why this billboard format works

Puzzles force people to stop, think, and mentally participate instead of just glancing and forgetting.
The three easy designer names act as social proof that the mystery brand belongs in elite company.
Calling itself “the least known of the four” is disarming honesty that makes the ad more believable.
The tiny logo becomes the hero, so anyone who solves the puzzle locks that visual into memory.
You can literally measure brand lift by how many people recognize or ask about the mystery logo afterward.

Ways to steal this idea for your brand

Tommy Hilfiger could rerun this exact concept today with updated competitors to instantly test whether the flag logo still earns a top-four spot in people’s heads.

Samsung could run a highway billboard that shows three fully named smartphone brands plus one blank outline of its own phone to see if drivers mentally supply the missing name.

A new direct-to-consumer watch startup could copy the Times Square layout with three iconic watch brands and one mystery logo to position itself as the scrappy fourth contender.

Creative Variations