4 Iconic Artists Who Just Missed the 27 Club

Through the equally intriguing phenomena of celebrity and coincidence, the infamous 27 Club has developed an ominous lore around its unlucky members, all of whom died at the young age of 27 at the height of their fame. While there are countless people from the entertainment industry who died at this age, we most closely associate the 27 Club with rockstars like Jimi Hendrix, Jim Morrison, Janis Joplin, Amy Winehouse, and Kurt Cobain.

Substance abuse and its pervasiveness in the music industry are certainly to blame for these icons’ deaths, not a bad cosmic hand. Still, the latter explanation provides greater allure than the former. This mystery, in turn, makes the tragic deaths of other artists who just barely made the infamous club more ominous, too. We take a look at four almost-27 Club members.

Otis Redding

A 26-year-old Otis Redding died in a tragic plane crash in Wisconsin on December 10, 1967. Redding, who was well on the ascent of his career, had just bought a private plane to travel to performances. This particular night, they were headed toward Madison, Wisconsin, to play at the Factory nightclub. Redding’s plane was only four miles from the airport when they crashed into the icy Lake Monona, killing everyone on board but musician Ben Cauley.

Interestingly, one of Redding’s most iconic hits, “(Sittin’ On) The Dock of the Bay,” was a posthumous success. Redding tracked most of the song with the exception of one verse, which he whistled, and planned on returning to the song later to finish it. After his death, Atlantic Records released the unfinished version, whistle and all—the first posthumous No. 1 single in U.S. history.

Mac Miller

Rapper Mac Miller was a tragic example of an artist who would eventually succumb to the very problems he often talked about in his music. The “Best Day Ever” rapper was outspoken about his struggles with substance abuse and depression. He ran into a series of legal issues in the early 2010s, including drug possession charges and copyright infringement lawsuits.

On September 7, 2018, Miller’s personal assistant found him unresponsive in his Studio City home. He was 26 years old. The Los Angeles County Coroner’s Office listed Miller’s cause of death as a toxic mix of fentanyl, hard drugs, and alcohol. In 2022, a federal judge sentenced Stephen Walter to 17.5 years in prison for distributing fentanyl to the musical artist. Miller’s estate has continued to release his music posthumously, including Circles in 2020 and Balloonerism in 2025.

Gram Parsons

Grams Parsons’ instrumental and songwriting talent put him in the middle of some of the most iconic music of the mid-1960s to mid-70s, including the Byrds, the Flying Burrito Brothers, as a solo artist, and as a collaborative artist with other stars like Emmylou Harris. He died while vacationing in Joshua Tree National Park from a lethal combination of morphine and alcohol.

Before his death at 26 on September 19, 1973, Parsons allegedly told road manager Phil Kaufman and roadie Michael Martin that he wanted his ashes spread at Joshua Tree. When his family opted for a New Orleans funeral instead, Kaufman and Martin stole Parsons’ coffin from the Los Angeles International Airport to fulfill the musician’s wishes. The two men pled guilty to misdemeanor theft in November 1973. The judge gave the co-conspirators 30-day suspended sentences, $300 fines, and a joint fine of $708.

Nick Drake

Nick Drake is one of many folk-centric artists of the late 1960s and early 1970s who gained fame posthumously. His third, final, and arguably most iconic album, Pink Moon, marked a shift in Drake’s life where he transitioned from recording and performing to obsessively writing in the early morning hours in his parents’ home. He died at the age of 26 on November 25, 1974, from an overdose of amitriptyline, an antidepressant. The coroner determined his death to be suicidal.

Drake’s final album, Pink Moon, seemed to be an ominous foreshadowing of his death. After hearing the record for the first time, Folk singer Beverley Martyn said, “I thought, ‘This boy’s gone. We’ve lost him. We can’t reach him anymore, and he can’t reach us.’ Pink Moon is like the Book of Revelation. It doesn’t make sense, and it’s a manifestation of illness, of madness. Those words were the product of a sick person” (via The Guardian).

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