Periodically, I browse through the computing section of bookstores. Over the years, I take out dated books but leave in the classics. Tell students what you expect them to get out of the artifact and what they are supposed to do with it. I rarely test students on this material, preferring to emphasize class discussions and writing. Not everything works.
Some material goes over the students' heads or is culturally specific.
Students may not find the jokes and ads as relevant or funny as you do. But this should not really worry you. Choose the artifacts with your interests in mind. This shows students that instructors have pastimes and concerns beyond the technical aspects of computing. Emphasize the connections between topics.