At the turn of the 20th century, there were an estimated 100,000 cigar “factories” in the United States. With so many cigar makers in business, it took something extra to snuff out the competition. A colorful label with eye-catching art, pasted to the interior of the cigar box lid, was one way to whet the buyer’s interest.

This was particularly effective in an era when nearly half of America was illiterate. Inside humidified display counters, open cigar boxes featured the varied brands, plus their visual identifiers. Prospective customers may not have been able to read the manufacturer’s name, but they remembered the picture.

Cigar box art actually owes its existence to Abraham Lincoln. At the height of the Civil War, with additional revenue needed, Lincoln proposed a luxury tax. Among those luxuries: perfume, playing cards—and tobacco.

The tobacco tax was imposed in 1863, but enforcing it proved a nightmare. Shipping barrels were customarily packed with 2500 or more cigars. Making sure each cigar was taxed proved.

. .well.

. . taxing.

In 1865, new regulations solved the counting conundrum. All cigars, whether domestic or imported, were now packed in wooden boxes of 25, 50, 100, or 250. Boxes sealed with an IRS stamp guaranteed that taxes had been paid.

After the war, thanks to greatly reduced taxes, the introduction of cigar molds, and an influx of immigrant labor, cigar-making became a profitable enterprise. By 1900, it’s estimated that 4 out of 5 men (plus an u.