Trey Anastasio Opens Up About Phish, Sobriety & His Musical Heroes In Howard Stern Debut

Trey Anastasio made his first appearance on The Howard Stern Show on Monday, November 2, joining the broadcaster for an extensive conversation about Phish, his recovery from addiction, his childhood and the musicians who continue to inspire him. Keyboardist Jeff Tanski accompanied Anastasio for acoustic performances of “Pebbles And Marbles” and The Rolling Stones’ “Loving Cup” at SiriusXM Studios in New York City.

The latter selection marked Trey’s first acoustic rendition of “Loving Cup” since December 2, 2005 at San Francisco’s Warfield Theatre, according to Phish.net. The two songs complemented an interview filled with personal revelations, stories about his musical heroes and insights into the work behind Phish’s spontaneity.

Stern arrived prepared with archival performances and questions about everything from Anastasio’s classical training to his attachment to his Paul Languedoc guitars. The host repeatedly expressed admiration for Trey’s musicianship, while the guitarist spoke enthusiastically about the friendships and sense of responsibility that have sustained his career.

The visit to Stern’s New York City studio comes as Anastasio prepares for two Divided Sky Foundation benefit concerts with Billy Strings later this month and Phish’s 100th show at Madison Square Garden in January. Stern, who called himself a fan at the top of the segment, steered the conversation toward subjects Anastasio said he has rarely discussed publicly. “I’ve been pretty quiet about all this for most of my life,” the guitarist said at one point.

Early in the interview, Stern challenged the idea that accomplished musicians simply possess a gift that allows them to bypass years of practice. Anastasio agreed, pointing to Jon Fishman as an example. According to Trey, the drummer still practices three to four hours on show days, including backstage at Madison Square Garden.

That commitment extends to Anastasio’s writing and preparations. His parents required him to spend a year studying classical guitar before getting an electric instrument. Later, composer and mentor Ernie Stires assigned exercises such as Bach-style two-part inventions and big band arrangements. Early Phish compositions, including “Foam” and “Split Open And Melt,” were written with pencil and paper, with instrumental parts charted out.

“You try to make it look like a magic trick, like it all just happens,” Anastasio said. “But it does not.”

Stern connected that work ethic to Anastasio’s father, bringing up their interactions in the documentary Between Me And My Mind. Trey acknowledged that their relationship had been difficult, recalling being required as a young child to complete hundreds of hockey shots in the basement before dinner.

Anastasio emphasized that he and his father are close today and have worked through those issues. He described the death of his sister from cancer as a turning point that softened relationships throughout the family. His sister had been a protector and source of support, taking him to his first Bruce Springsteen concert and helping him financially when he was a young musician.

Both men are devotees of the late Dr. John Sarno, and Anastasio said he has given Sarno’s book Healing Back Pain to 20 or 30 people. He explained that he was obsessing for months over the logistics of Phish’s 2017 Baker’s Dozen, 13 shows at Madison Square Garden without a repeated song, when his back gave out. After an MRI showed herniated discs and a doctor told him he might never be pain-free, someone left the book in his band room. “I read it and then I read it again,” Anastasio said. “I’ve never had that pain again.”

The discussion led to Anastasio’s addiction and his reluctance to recount drug stories that listeners might mistake for rock-star mythology. He described how substance use became entangled with workaholism, as he convinced himself that drugs would allow him to spend more hours writing.

Anastasio said his main addiction was opiates and that by the end it included OxyContin, heroin and cocaine. He traced the spiral to around 2000, when a doctor began writing prescriptions to get himself into Phish’s crowded backstage scene at Madison Square Garden. He said he has long avoided the subject for fear of romanticizing it:

I hate it when rock musicians glorify this stuff in any way, shape, or form as if there’s anything other than horror in hard drugs. They’re so bad, and I am always worried that if I talk about this, some kid is gonna think it’s cool, and it’s just incomprehensibly uncool.

Anastasio called his December 2006 arrest in Whitehall, New York “the greatest thing that ever could have possibly happened.” He spent two nights in the Washington County jail, where a night guard who had seen Phish at nearby Saratoga Performing Arts Center recognized him through the bars around 2 a.m. “I’m like, ‘Please walk past. Please walk past,’” Anastasio recalled. He completed 14 months in a drug court program, during which he took 120 drug tests, followed by three years of probation that required him to submit his tour routes in advance. His case manager, Melanie Gulde, later co-founded the Divided Sky Foundation with him, and its residential recovery program in Ludlow, Vermont opened in 2023.

Anastasio also described making amends during his recovery. When he apologized to longtime Phish sound engineer and luthier Paul Languedoc for how he had acted, Languedoc told him, “You just kept apologizing.” Anastasio said his real shame was the quality of the shows, and that walking offstage after playing poorly in front of 25,000 people fed the cycle of using.

Stern revisited one of Phish’s most celebrated collaborations: Neil Young’s appearance with the band at Farm Aid on October 3, 1998. Anastasio explained that he and Young had actually rehearsed “Powderfinger” on a bus before the performance. As Trey left, Young warned that he was not particularly good at planning.

Young then played “Powderfinger” during his own set, leaving Anastasio to assume their collaboration would not happen. Instead, Young later walked onstage behind Trey, picked up one of his guitars and began playing without an announcement. Anastasio remembered hearing his instrument produce notes he was not playing before realizing what was happening. The musicians eventually found their way into “Down By The River.”

As Stern played the footage, Trey delighted in the spontaneity of the encounter and the fact that their preparation had led somewhere entirely different.

A Bruce Springsteen story illustrated another quality Anastasio admires: generosity. Trey recalled asking The Boss to join his band for “Kitty’s Back” at Sea.Hear.Now in Asbury Park, where Springsteen sat in on September 15, 2024.

Anastasio marveled that Springsteen would entrust one of his own songs to another band shortly before headlining such a meaningful event. TAB learned the song carefully, and Springsteen showed up ready to play. That willingness to participate, Trey suggested, helps explain how an artist sustains a career across decades.

The conversation also provided a revealing explanation of how Phish balances preparation with freedom. Before a concert, Anastasio may check whether his bandmates are comfortable playing particular songs. Sometimes someone needs more practice, and the band adjusts accordingly. Once onstage, however, Trey wants to commit fully to the show happening that night.

“What I don’t do is save anything. Ever,” he said. Rather than hold a song for later in a run, he approaches each performance as though there is no tomorrow.

His account of planning the Baker’s Dozen residency offered another glimpse of the work involved. Anastasio recalled obsessing over the challenge of playing 13 Madison Square Garden shows without repeating songs, arranging Post-it notes across the floor and continuing to work on possible sets while traveling to the venue.

That drive comes from wanting to honor the audience’s investment in the band. Anastasio acknowledged a pattern in which he would volunteer for work and then resent how much he had taken on. Underneath it was a determination to give even the most seasoned fans something extraordinary, whether a spectacular production or an unexpected cover.

“They deserve everything,” Trey said.

The discussion of influences included a vivid description of his relationship with Jimi Hendrix’s “Machine Gun” solo. During the mid-1990s, Anastasio regularly listened to it before shows in a darkened bus lounge with the volume turned up. He described Hendrix’s guitar playing as speech, with distinct musical paragraphs and shifts in subject, and acknowledged absorbing that approach into his own playing.

He also recalled handing Frank Zappa an early Phish T-shirt from the audience and watching his hero hang it on an onstage laundry line.

Asked about Phish and the Rock & Roll Hall Of Fame, Anastasio found humor in the band’s position. “I always think in a weird way it’s kind of appropriate because we’re in the lobby,” he said, referring to the band’s flying hot dog display.

Trey described Phish as a joyous “island of misfit toys” and emphasized how much the four musicians still enjoy one another. That closeness takes maintenance. Anastasio compared being in a longtime band to getting into a van with friends at 18 and remaining there into your 60s. Conversations and work are necessary, he explained, and Phish has prioritized those relationships over success.

His affection for Billy Strings was equally evident. Anastasio said the two connected early over difficult experiences in their lives and now spend hours talking. He expressed a desire to see the younger guitarist take care of himself and enjoy a long life.

“I’m happy for the planet that he’s on it,” Trey said.

Anastasio previewed their upcoming Divided Sky benefits, explaining that Strings will have an opportunity to play plenty of electric guitar with Trey Anastasio Band. Their shared enthusiasm for metal has prompted some adventurous song ideas, although they were still working out the material. The concerts take place November 20 and 21 at Worcester’s DCU Center.

Another emotional passage centered on Anastasio’s koa Languedoc guitar (Koa 1), built in 1996. He described developing his playing style around the instrument’s hollow construction and feedback, as well as the significance of having played it during Phish’s overnight millennium performance at Big Cypress.

Even with newer instruments available, the connection remains difficult to replace. Anastasio said he can nearly cry when his guitar tech hands it to him before a Phish show.

The performances with Tanski brought the conversation back to the songs themselves. Discussing “Pebbles And Marbles,” Anastasio spoke about daughters retaining access to a childhood magic that can feel distant to an adult. Afterward, he reflected on his songwriting partnership with Tom Marshall and the value of having collaborators who have known him since childhood.

“Loving Cup” prompted an entertaining account of Keith Richards’ command of his rock-star persona. Anastasio recalled Richards smoking at Late Night With Jimmy Fallon, a fire alarm going off and the guitarist emerging in a different outfit for a backstage photograph with members of Phish and The Roots. Trey was struck by the care Richards brought to an appearance whose central assignment was simply introducing the band.

As for The Rolling Stones’ “Loving Cup” itself, Anastasio praised the balance of danger, spirituality, hope and community in Mick Jagger and Richards’ songwriting. It occupies exactly the emotional space he wants at the end of a concert.

Before playing it, Trey made clear that his enthusiasm for performing has only grown.

“It never gets old,” Anastasio said. “Now is more fun than ever.”

The visit ended with a playful exchange about Stern potentially singing King Crimson with Phish at the band’s 100th Madison Square Garden performance on January 2, 2027. After Stern offered his services, Anastasio floated the milestone concert as a possible occasion, prompting another joke from the host.

SiriusXM subscribers can hear replays of the interview on the Howard 100 Channel. A 90-minute edit of the episode will air on HBO Max this Thursday, November 5.