Between 1870 and 1920, tobacco use was endemic in Europe and North America, and cigar smoking was its most popular form.

To meet Canadian demand, entrepreneur cigar makers, many from the British Isles, Germany, and Russia, established hundreds of factories, large and small, in cities and towns from Victoria to the Maritimes. They hired and trained local men, women, even children to hand roll cigars using domestic and imported tobacco leaf.

In the early days, the finished cigars were tied into bundles and sold in bulk to vendors. The federal government sent officials to factory warehouses to collect taxes on cigars by weight or by the 1000—a calculation too imprecise to ensure that taxes had been paid on every cigar sold.

In 1868, the Ministry of Inland Revenue adopted the cigar box as a taxable unit. They issued new revenue stamps and instructions for their use: "... the long labels [i.e., revenue stamps] for cigars are to be passed entirely around the cigars boxes, and the ends lapped over each other keeping the printed side of the label outwards, and they are to be glued or pasted entirely around the box so that they cannot be removed." But even in box quantities, cigars were still taxed by weight.

In 1883, the government changed this: it legislated that cigars must be packed for sale in wooden boxes holding 10, 25, 50, 100, or 200 cigars. A newly designed revenue stamp showed the number of cigars in the box that had been taxed.

Revenue stamps retained their long strip form until 1922. After that, boxes were sealed with stamps just long enough to cover part of the lid, the front, and a portion of the bottom of the box.

By 1897, manufacturers were naming their cigars and pasting a colourful label illustrating the name on the inner lid of the box.

Cigars were sold out of their open boxes arrayed in tobacco store display cases.

The colourful labels on the inner lids acted as miniature billboards, competing with each other to attract the passing eye of the customer.

Catchy brand names and vivid imagery invoked the news of the day, popular phrases and catchwords, gender and ethnic stereotypes, and the growing cult of celebrity in politics, sports, entertainment, and the military.

As a result, cigar boxes from this era provide tantalizing vignettes of everyday life in the new country, Canada.