My all time favorite tobacco is the old VaPer Three Nuns.
It's hard to pick a favorite pipe. For sentimental reasons, there's my dad's pipe as well as the first one I bought, which is a 1974 Dr. Grabow Omega. It cost $2.49. I had one dollar. My neighborhood buddy, Dale, was going to mow the family lawn, for which his dad paid him $3. I talked him into letting me mow two dollars worth of the yard so I could buy the Grabow, and had money left over to get a pouch of tobacco, which was Borkum Riff Whiskey.
My best smoker is probably my straight sandblasted pre-transition Barling Exel 249 Fossil T.V.F. black billiard with a silver band and a black ebonite military bit. That also has a lot of sentimental value as it was once owned by one of my best friends (Donald). When he passed away, I inherited his collection of seventy pipes, which includes most of the expensive ones in my collection (Ardors, Rinaldos, Karl Eriks, etc.). I was with him when he bought the Barling, and I said to him, "You know, this is the first pipe you bought that I have a little envy for." Donald said, "Well, if anything ever happens to me, it will be yours." He passed away from pancreatic cancer six years later, and every time I smoke the Barling, I remember that conversation, and miss my old friend.