Good subject
If you want to see movies with pipes, you're either going to need to watch period pieces (movies set in times when pipe smoking was more prevalent) or old movies. I've noticed that pipe smoking either falls into one of two categories: in character smoking or comic/prop smoking. In character smoking simply means that the character is smoking because that's a part of the character. Lust for Life is an example. My current avatar is a still taken from My Man Godfrey (1936) that shows William Powell's character smoking a pipe. Another example would be Melvyn Douglas and Cary Grant in Mr. Blandings Builds His Dream Home (1948). Their characters were very affluent (I think a lawyer and an advertising exec respectively), and they almost always had upscale pipes lit. There is so much pipe smoking in that movie that I wonder if some pipe company was producing the movie haha. Of course, you also have the Sherlock Holmes movies (Basil Rathbone, Robert Downey Jr., etc.). Then you have some comic characters like Will Ferrel (Anchorman and Land of the Lost) or Pa Kettle in the Ma and Pa Kettle series.
The other category would be what I call the comic/prop category, and that is simply using the pipe as a gag piece and not really out of character reasons. Stan Laurel sometimes used a calabash to stand as a contrast between Sherlock Holmes/intellectualism and his character. Abbott and Costello, the Bowery Boys, and others have also used pipes for such purposes. You could also argue that the Will Ferrell examples cited above may also fit in this category too.