Steve Laug had this posted on Reborn Pipes about 10 years ago. I saved it and used it as my phone screensaver for a long time. A fan of the blog made the drawing.
We have two small oil paints with sea captains/fishermen smoking pipes. Unfortunately, when we did some remodeling they were put into our storage unit and are among the paintings the wife decided to leave in storage.
I have been told I remind some of paintings like this because I like to wear bulky sweaters when it gets cold.
Here is a painting by Alan Lee presented in chapter 1, "A Long-Expected Party", of The Fellowship of the Ring. Gandalf lighting his pipe while talking with Frodo after Bilbo's departure.
Not an artist's painting rather the man himself as an artist. The lovely Ron Carter.
If you aren’t already familiar check out the Ser Jacopo ‘Picta’ series. Giancarlo’s interpretations of pipes on canvas.