One of the joys of modern technology is how easy it is to immerse yourself in the past. Every day, more libraries and archives are pushing pieces of their collections online in easily browsable interfaces.

The New York Public Library, for instance, has historic menus and interactive floor plans. Chronicling America is a searchable repository of newspapers published between 1836 and 1922 from the Library of Congress, which is also one of the many institutions in the Flickr Commons public image archive. Wikipedia has its own Wikimedia Commons, to which anybody can upload images and videos. Project Gutenberg continues to add new public-domain books to its collection every day, and New York’s Metropolitan Museum of Art has posted thousands of images online with metadata as part of its Open Access for Scholarly Collections initiative.

My personal favorite however is TimesMachine, a site available to all New York Times subscribers that lets readers virtually flip through any historical issue of The New York Times all the way up through 2002. The site delivers the reader directly to the past, making you feel like a cross between a tourist and an archaeologist. You might start by visiting a historic event—say, coverage of the Titanic sinking—but the real fun is wandering off the beaten path and exploring all the other news of the day. On the same day the Titanic sank, there was also coverage of a gun battle in Greenwich Village, and a passenger lost in a runaway balloon. On any day, such vignettes sometimes become rabbit holes to the past.

This is the story of how I ended up captivated by a chance encounter with a 135-year-old newspaper advertisement—and how the random face staring back at me from the archives would reveal the surprising origins of ASCII art, a graphic design technique that’s usually associated with 20th-century computer art.

Way back in 2001, the New York Times hired ProQuest to digitize the vast majority of its archives—dating from the paper’s founding in 1851 to 1980, when the Times started keeping electronic copies of article text. The Times had already published a complete index of all its articles since 1913, but it wanted the full text of its archives to be digitized and searchable. Much like book digitization, the first step of this process was scanning each page from the source material. However, unlike books, newspapers are not single columns of text. This complicates thing because each page has to be individually analyzed and partitioned into zones of related text. Those zones that were identified as Times articles were then linked to metadata from the existing Times Index—and scanned into electronic text, making the archives largely searchable. But it wasn’t until 2008 that it was possible to look at entire issues from the archives—that is, page-by-page copies of the paper as it appeared at the time of publication—when Derek Gottfrid, a developer at the Times, figured out how to cheaply stitch together zones back into pages for the first version of TimesMachine. In 2014, the Times’s R&D unit revamped TimesMachine with a new viewer that worked like Google Maps—a functionality that made load times fast and zooming-in intuitive. In 2016, they extended its coverage past 1980.

Ever since the beginning of the project, I was entranced by all the advertisements, each era embodying its own style and charms. I was a software developer at the Times working in the cubicle next to Derek when he built TimesMachine, and I felt the ads deserved a viewer all of their own. Unfortunately, this wasn’t so easy. Since ProQuest was only interested in articles, they ignored everything else that had appeared in the paper, and that everything could be anything—advertisements, photographs, weather charts, section titles.

So the only way to figure out what ProQuest left behind is to look back at each and every page of the paper. This was the idea behind Madison, an experimental project from the Times’ R&D Lab that identifies ads through crowdsourcing a series of simple and complicated tasks. (The most dedicated users can help transcribe the text of ads or identify the companies and business category for the ads; more casual contributors can just click through one unknown zone at a time, marking which contain ads and which do not.) It’s a project that will likely never end; there are millions of these zones, and once you click past, the odds are almost certain you will never see the same thing again. It’s fun to explore this way, clicking through the past, one ad at a time.

Before Madison existed, I built an ad viewer that worked in a similar fashion, randomly loading one of these zones on each request. Because I wanted to tweet my most interesting finds and didn’t want to fret about copyright, I limited my searching to the public-domain era before 1923. It quickly became my favorite way of killing time when I had a few minutes before a meeting, or I was on hold for a phone call, or I had some code to compile. I found so many interesting ads this way, one click at a time.

There were four lines in the classifieds from 1855 that exclaimed “Why in Thunder Don’t You Use My Onguent!” and promised to force luxuriant beard growth on any face. Click. Then there was the 1921 Lord & Taylor ad declaring “Easter Modes Have Potent Charm” Click. And an 1861 ad announcing the April issue of a magazine called the Atlantic Monthly. Click. A lavish 1922 Bonwit Teller ad proclaiming “En Route Costumes for Feminine Travelers” Click. A distinctively-drawn appeal for fancy cigarettes from 1911. Click. A July 1889 advertisement for an opera at a theater air-conditioned with blocks of ice. Click. An 1865 teething syrup for infants that secretly contained morphine. And so on.

And many times, the tool I built would return nothing useful at all—maybe the fragment of a page, or the title of a section, or some random block of text that should have been attached to a story but was lost in the process. More frustratingly still, many images were often marred or completely illegible. ProQuest’s process began with microfilm of newspapers that had already been decaying for decades, and they in turn made high-contrast black-and-white scans that are fine for scanning text, but that rendered many photographs murky. “Generation loss” is the technical term for this chain of imperfections, the ways in which each step of digital processing adds its own distortions. I knew it as the ironic consequences of the same processes that made it possible for me to view these advertisements in the first place. I could always hope for better luck when I loaded the next image. Click.

Which is how one day I stumbled across the Treasurer, and found myself confronted with a mystery. It was the full-faced portrait of a man with a sleepy smile, wide nose, prominent lapels and a jaunty bow tie. White-space details emerged from a background made entirely of the repeated letter B. Above his head is only the simple caption “The Treasurer” and below is a generic listing for the Brooklyn Furniture Company. I couldn’t believe what I was seeing.

Old NYT Ads / Flickr

The face resembles modern ASCII art, but it was published at a time— March 20, 1881—that seemed impossibly early. I checked to see if there were other ads like it—a tedious process that required me to virtually flip through old issues one page at a time—and surmised it only ran once in the spring of 1881. Because ASCII art involves using small textual elements—letters, apostrophes, dashes, and so forth—to create a larger design, it's impossible to search for such ads using keywords like “Coca-Cola.” To the computer, the ad just looks like a meaningless sequence of repeated characters. No other ads by Brooklyn Furniture Company appeared in the Times in the weeks before or after the ad I had found. Nor could I find similar text-based art from any other advertisers around that time. I assumed it was just a strange unicorn from the archives, a weird invention from a bored printer who just accidentally had invented ASCII art. For a while, I forgot about it.

Until I found another.

On February 27, 1881, the Brooklyn Furniture Company ran an ad proclaiming “the President of the Brooklyn Furniture Company has decided to make sweeping reductions in prices,” and it featured the side profile of a genial and balding man rendered simply in text using the letters B, F, and C. Now there were two mysterious faces. I decided it was time to find out more about what exactly the Brooklyn Furniture Company was.

Old NYT Ads / Flickr

Located in three storefronts on Fulton Street, the firm was founded in the 1870s as the Bridgeport Furniture Company, but soon changed its name to reflect the rising fortunes of its borough. In ads, it promised “liberal credit” and layaway for those who couldn’t pay full price. And it was a prolific advertiser, apparently locked in a fierce struggle for customers against similar furniture retailers in New York. In an 1899 profile, the president of the company told the advertising publication Printer’s Ink that he had spent up to $80,000—the equivalent of $2.5 million today—entirely on newspaper advertising in the previous years. Another Printer’s Ink article, in 1901, reported that the company spent more annually on advertising than all 23 of London’s top furniture stores combined, and noted that a competitor thought nothing of spending more than $2,000—roughly $57,000 in today’s dollars—on just one single day of advertisements in all the Sunday newspapers. For context, a full-page ad in the Sunday Times can run you more than $100,000 today, according to a 2014 story in the Times. But the media landscape in the 1890s was not like today. There were 58 daily newspapers in New York City alone, and although we think of it as a giant today, the Times itself was firmly in the middle of the pack. I had seemingly wandered into the early skirmishes of a wide-ranging advertising war. Was it possible there were even more ads like The Treasurer out there? I needed to look at other newspapers.

And so I joined newspapers.com, a commercial archive of newspapers that has digitized text from stories and advertisements. I quickly found several other instances of the President ad, with its first run in The Sun on the early day of October 13, 1878. And I soon found many other instances of text art too. The front page of the Brooklyn Daily Eagle from June 14, 1877 includes several companies that spelled out their names in large capital letters formed by regular-sized letters—a format I call “ASCII Caps”—while the Brooklyn Furniture Company waggishly chose to run “MY WIFE” at the top of its ad, presumably as a way to capture readers’ attention.

A Brooklyn Furniture Company ad published in 1879 in the New York Sun. (Jacob Harris / Wikimedia)

It seemed that many of the newspapers of the era carried such illustrations, with large titles and sometimes simple shapes like hearts and crosses all composed out of type. I know it as ASCII art, but it appeared roughly a hundred years before the personal computer even existed. Of course, before there were computers, there were typewriters, and the first recorded instances of typewriter art date back to at least 1893, but I’d never seen a record of any other ASCII-type art as early as the 1870s. I felt like an archaeologist who picks up an ancient clay urn and finds a modern emoji on it.

The Brooklyn Furniture Company's designs would look right at home on a Geocities page or designed within Broderbund’s The Print Shop software, because they all stem from the same need: to be more expressive than technology otherwise allows. In the early days of computers, those first graphics were text inside terminals or printed by daisywheel printers. However, unlike other ASCII art, the designs in these newspapers were definitely not created on typewriters—but painstakingly composed one letter at a time with blocks of type by professional typesetters. Nor are they actually art per se, but stylistic tactics employed to exploit scarcity as an advantage.

For most of the 19th century, newspapers were slim things. Every page had to be typeset by hand, meaning that the largest daily newspapers stretched to only 8 or 12 pages—and many were even shorter. Advertisers soon figured out how to exploit this scarcity of space by buying more ads than they needed, perhaps to deny their competitors any room. But once they had all that real estate, what do they do with it? The first and simplest approach was just repeating the same 3-line advertisement over and over again. Next, advertisers soon learned to add large amounts of blank space to make their ads pop more on the page, but that still didn’t make them any more visible from a distance. Bigger text was the next logical step, but it’s not clear whether that was technologically possible—or, if it was, economically viable. An ingenious solution emerged: What if, instead of giant letters, you could build large letters out of smaller blocks of text? I haven't yet figured out the exact point when and where this practice started, but I did learn that it predated even the 1870s. I found an 1860 ad for hoop skirts in the shape of a skirt. And in 1862, Smith & Brothers brewery in New York placed ads with ASCII text in several papers nationwide.

The Brooklyn Daily Eagle

The Brooklyn Daily Eagle

In many newspapers, these early examples of text art vanished not long after they arrived. Only months after the 1878 ad of “the president”  in the Sun, such designs had seemingly disappeared from that newspaper, and apart from the two advertisements I had found, the style apparently never caught on in the Times. But why not? To answer that, I looked more at the Eagle where I found the earliest ads—and where they survived for several decades longer than everywhere else. They are there in 1881, when one bold advertiser filled an entire page with ASCII text. There are there in 1888, when the Eagle advertised its election night almanac in the familiar large letters. They are there all the way up to July 3, 1892,  a day the same Brooklyn Furniture Company again ran a half-page ad with their address in large ASCII letters. And, then, on July 5th, they were completely gone, replaced by modern layouts and fancy typography. Those upgrades likely explain, at least in part, what happened. ASCII art flourishes most when technology is limited; you don’t need Print Shop anymore when you can do digital layout on your computer and have an inkjet printer.

The Brooklyn Daily Eagle

The late 19th century was an era of rapid technological innovation for newspapers, as new technologies like hot metal typesetting made it easier and faster to compose each page. This in turn allowed newspapers to expand in size—reducing the advantage of scarcity for advertisers, but also offering more options for them. This likely happened at various points in the 1880s for various newspapers, but I was able to trace the Eagle’s transition to an exact date. Along with the half-page Brooklyn Furniture Company ad that appeared on July 3, the Eagle ran its own ASCII ad that day to announce that their new offices would open in two days. Then, on July 5, the Eagle ran a short item proclaiming its new building as having the “finest composing room in the country.” In other words, the Eagle had finally upgraded its old technology, and with that, the first era of ASCII ads was suddenly over.

More than a century later, I’m still left with many questions. For starters, why was the Brooklyn Furniture Company seemingly the only advertiser to make portraits this way? Did the first ASCII advertisers have any sense of what they had done—or were they, in fact, drawing inspiration from some other source, perhaps hiding somewhere in the dusty annals of publishing history? Online archives made this whole search possible, but I would love to know so much more about this era from the perspective of the printers and the advertisers and the readers. But all those involved are long dead—even the Brooklyn Furniture Company itself was absorbed by a competitor in 1929. So I can only guess at motivations from what small scraps of the past I have observed. The observations themselves have been somewhat arbitrary, based on wanderings through the archives and lucky happenstance. Ultimately, I am more of a tourist than a time-traveler. After all, no digital collection can fully reveal what the past was really like. There will always be mysteries left unexplained.