This one goes way back into my ol' Papel Freelance/Russ Berrie days where we designed novelty gifts. This design was created somewhere around 20 years ago for a Father's Day mug.
The work itself was done by first drawing four pen & ink illustrations. I had to do some old timey library searching for black & white photos to use for reference. Then I needed to create poses that worked well together to create a balanced composition, Once that was done, I took the image, reduced the size, flopped the film and created a repeating pattern in the background. Final stage, everything had to be rubber glued into place on a heavy press board.
Today, this could easily be done on computer in a heartbeat. But back then, this job was tedious. I had to measure everything and figure the proper spacing for the repeating images in the background. As you can probably see, everything had to be hand cut using an Exacto knife.
I do remember that they liked the design so much, I was "awarded" by having to do another similar design with golfers.