Let’s go back 20 years to a fascinating time in music history. In 1998, the internet had not yet become the hub of how we listen to music — Napster was still one year away from taking over college campuses, and listeners were still required to fork over $18 for a CD to hear that one Barenaked Ladies song they heard on the radio. And yet 1998 was in many ways the beginning of what music would become in the 21st century. Alternative rock and gangsta rap, which had dominated youth culture just a few years prior, were basically over, paving the way for a new generation of artists. To help me revisit 1998, I called up Judy Berman, a fine critic who has written for the New York Times, Pitchfork, The Atlantic, and many other publications. We talked about our personal favorites, our “most 1998” albums, and the one 1998 classic that I feel is kind of sort of overrated.