This week, Jason Whissell of It’s Not That Bad and There Can Only Be One joins me to tackle one of the trickiest challenges in music: the sophomore album.

Every artist here released both their debut and follow-up in the ’90s, making the challenge even tougher. And yet, these second albums didn’t just survive the pressure — they proved the first record wasn’t a fluke.

From alternative rock and beyond, these follow-ups sharpened sounds, expanded identities, and in some cases, outshined the debut entirely. If you love ’90s music, deep dives into discographies,  ...