I thought I'd feature on my favorite artists from this thread, John Sloan. He was a member of the Ashcan School. There's was a reaction to some of the movements of the time. They saw painting as adding the element of color to drawing, with the drawing directing everything. Here is an 1898 photo of the ashcanners in Sloan's studio. He's the one in front with the hat and pipe.
A great fan of his pipe, it's shown in a fair number of self portraits. Here are two with a self caricature.
He also painted other famous people who smoked a pipe. Here is a painting of Yeats at Petitpas and a stab at a Sherlock Holmes puzzle, though, to me, it looks an awful lot like Sloan himself.
Here are two of my favorites from part 1 of this thread.
McSorley's Bar from the 1920's
the tailor's shop
a fishing scene I hadn't seen before
In his later years his work took on that kind of hyper realism like Edward Hopper but brighter. But the pipes disappeared. Wish I knew that story.