Anyone who tuned into Nirvana’s 1992 performance on Saturday Night Live bore witness to a legendary moment in rock music history. But those who looked a little bit closer, might have noticed more than how Kurt Cobain sang or played, but what he was wearing: a homemade t-shirt repping the punk band, Flipper.
Flipper was a band beloved by Nirvana, and was instrumental in shaping the band’s sound. Now, 21 years after Cobain’s tragic and untimely death, Flipper frontman and bassist, Bruce “Loose” Calderwood has died.
News of Calderwood’s death was first made public by the @whocaresanywaysf Instagram account, who shared a sad, yet painfully honest caption. “After a prolonged struggle with life, Bruce “Loose” Calderwood of Flipper passed away from an apparent heart attack earlier this week at the age of 66.”
Fans were devastated by Calderwood’s passing, leaving touching, often emotional messages beneath his smiley, almost cheerful photo.
“Cannot overstate how important Flipper was and how wonderfully fun and chaotic the shows were,” wrote one fan.
“The pain is over. He’s angelized now. The best times of Flipper are perfect, never forgotten,” commented another.
“You changed things. You won’t be forgotten,” added a third.
Calderwood joined Flipper as a singer and bassist in 1979, amid San Francisco’s burgeoning punk rock scene, replacing the band’s original singer, Ricky Williams. With Flipper, Calderwood recorded four studio albums and five live albums.
Calderwood left the band in 2015 after sustaining a serious back injury, but not before inspiring countless musicians that would become household names. Cobain went on to wear another Flipper t-shirt in the Nirvana music video for “Come As You Are,” and artists including Moby, Eric Avery of Jane’s Addiction, Henry Rollins of Black Flag, The Melvins and R.E.M. have all cited Flipper as one of the most influential punk bands of its time.
“Flipper has always been a means and a device for getting a message to people,” Calderwood said in a 2009 interview. “There’s definitely hope in this world. […] Whether we all make it through this or not, it doesn’t matter. The time is now and that’s what you f—-n’ do, is what you enjoy. It’s rudimentary, it’s all planted in our brains already, we just need to follow it.”
This story was originally reported by Parade on Sep 6, 2025, where it first appeared in the News section. Add Parade as a Preferred Source by clicking here.