I got my first CalComp tablet in 1995, used it a few times with Fractal Design Painter, before Painter was bought by Corel. Painter made Photoshop obsolete for a long time in terms of digital painting (unless you loved adding lense flares).
Still I didn't draw too often, I preferred sketching in pen and paper.
Then I got a Wacom Graphire in 2000's, that I used primarily with Photoshop, but still hardly used it.
Finally settling on the original Intuos in 2010, that my dad bought me used off ebay, using it mostly with Sketchbook Pro. I started to take my digital art more seriously then.