Too often, Bad Boy has been looked at as defining a certain period of music: the shiny suit era, everything jiggy, the producer dancing all up in the video. And while a half a dozen movements within hip-hop appeared in direct opposition to Bad Boy, the late 1990s yielded genre-defining music from the label’s flagship artists. Those cuts can still be heard reverberating from clubs and cars and house parties in every season, year after year. That stretch at the end of the last millennium has been imitated by labels and artists in the years since, but the feeling can never quite be restored.

Yet Bad Boy has always been so much more. From the Lox’s grit to Shyne and G. Dep’s tragic arcs; from Carl Thomas’s soul-baring ballads to French Montana’s minor-key maximalism—the label has come to cover the breadth of R&B and hip-hop. And with many of those major players joining forces for the label’s reunion tour, we’re taking a comprehensive look at the Bad Boy catalog to revisit the countless classics it put out over its 20-plus years in the game.

The playlist spans from the Notorious B.I.G.’s seminal Ready to Die to the present day. It catches founder Sean “Puff Daddy” Combs in a variety of moods, from the anthems of his debut, No Way Out, to more experimental fare like his Last Train to Paris. It highlights Bad Boy’s forays into R&B and pop while staying grounded in its rough-edged origins. It’s grimy, glossy, and everything in between—just like Bad Boy.