Above is not, strictly speaking, the first thing ever published by Dharma Press (now Dharma Publishing), but it is certainly among the first.
This picture by Sherab Palden Beru was published in August 1969, by Tarthang Rinpoche, on an Excelsior hand-powered printing press I helped to buy.
The original was published in the British magazine Middle Way, to illustrate an article by Trungpa Rinpoche.
I had the block done by M&H, in San Francisco. The gold for all of this came from washing dishes for USD $2.00 an hour at the Khyber Pass Restaurant, and whatever I could scrounge.
The signature at the bottom is that of H.H. Tarthang Rinpoche. This picture has survived fires, floods, and other disasters.
For the record, the first thing ever published by Dharma Press was a silkscreen work, and then, after the press was delivered, a little business card with the Seven Line Prayer.
Here is another picture, of Milarepa, by Sherab Palden Beru, done in Scotland circa 1968.