The 27 Club is equal parts tragic and fascinating. The term, of course, stems from the unique coincidence of many high-profile entertainers dying at the age of 27.

According to Rolling Stone, the term’s popularity skyrocketed after the untimely death of Nirvana frontman Kurt Cobain. His mother, Wendy O’Connor, even mentioned it following his death.

In a 1994 archival story from The Seattle Times, O’Connor said of her late son, “Now he’s gone and joined that stupid club. I told him not to join that stupid club.”

However, there were plenty of major names in the rock world who were members of this “club” long before Cobain died in 1994. This club and its members are explored in Howard Sounes’s 2021 book 27: A History of the 27 Club Through the Lives of Brian Jones, Jimi Hendrix, Janis Joplin, Jim Morrison, Kurt Cobain, and Amy Winehouse. The book’s synopsis reads, “In a grimly fascinating journey through the dark side of the music business over six decades, Sounes uncovers a common story of excess, madness, and self-destruction … A clear and compelling narrative emerges, one based on hard facts, that unites these lost souls in both life and death.”

Indeed, the members of the 27 Club are lost souls and unique talents gone far too soon. Despite this, they left legacies that have lasted for decades and will likely continue to do so. Yes, they will live on thanks to their art and impact on pop culture, but they’ll also be cautionary tales, which, frankly, isn’t a bad thing either. A life ending that young is simply devastating, and if it can be avoided, it should.

In the gallery below, we look at five of the club’s most iconic members arranged in the order in which they officially joined the club.

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