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Trey Anastasio Talks Crossing Paths with Neil Young, Keith Richards and Bruce Springsteen, Family Dynamics and More with Howard Stern

By Relix Staff

1:02 PM EST on November 3, 2026

Trey Anastasio appeared on The Howard Stern Show yesterday morning, sitting for a wide-ranging interview with the veteran radio host and offering a pair of unexpected acoustic selections. The high-profile meeting was recorded at Stern’s SiriusXM studio, which is located in New York’s Rockefeller Center.

Performing with his close collaborator and arranger Jeff Tanski on keyboards, Anastasio turned in stripped-down versions of the Round Room track “Pebbles and Marble,” which began its life as a solo piece that the guitarist happened to debut during a radio performance in 2002, and his now trademark take on The Rolling Stones’ “Loving Cup.” Though the latter tune remains a Phish standard, Anastasio had not performed the number in a solo acoustic context since a December 2, 2005, appearance at San Francisco’s Warfield Theatre that also featured guest turns by Bill Kreutzmann and Mickey Hart.

Over the years, Stern has gradually shed his original shock-jock persona and emerged as an inspiring interviewer and his discussion with Anastasio touched on a number of interesting topics. They riffed on many of the famous musicians Anastasio has crossed paths with over the years, including Keith Richards (who introduced Phish on Late Night but then changed shirts before their post-show photo), Neil Young (who rehearsed “Powderfinger” with Anastasio on his bus during a hang with Willie Nelson and Woody Harrelson before a planned Farm Aid sit in with Phish, only to call an audible, play the song acoustic himself and jam on different selections with the Vermont Quartet), and Bruce Springsteen (who honored Anastasio’s request to sit in with his solo band on the 1973 track “Kitty’s Back,” which the Phish guitarist hoped to hear at his first E-Street Band show decades earlier, despite the Boss being moments away from playing a big show on the beach in his hometown of Asbury Park, NJ).

At different points, Anastasio and Stern also dug into heavier topics, including the guitarist’s struggles with addiction and the 2006 arrest that he credits with saving his life. Stern, who had seen the documentary Between Me and My Mind, also pressed Anastasio on his relationship with his father. Anastasio admitted that his dad was tough on him when he was young—making him practice scoring 100 hockey goals in the family basement before dinner—and that music was an escape, but the Phish co-founder was careful to note that they ultimately worked through any strains in their relationship, as well as the lingering effects from his parents’ divorce, after he sobered up and his sister passed away in 2009 following a courageous battle with cancer.

While he admitted that he often shies away from discussing his drug use so not to glorify it, Anastasio described the mixture of OxyContin, heroin, cocaine and other hard drugs he relied on to stay focus and creative before Phish’s 2004 breakup, tracing his downfall back to a doctor who hung around backstage and wrote him prescriptions to gain access circa 2000. Their conversation also explored Anastasio’s ongoing recovery as well as the three days he spent in jail, where a night guard who had seen Phish at SPAC recognized him behind bars. (Anastasio wasn’t anyone’s “bitch,” as Stern joked, but he did accept ramen from a fellow prisoner and played cards to pass the time.)

At one point, Anastasio riffed on his years in therapy, admitting he’s currently on a pause, as well the men’s group he regularly meets with, his bond with Billy Strings and the time he apologized to longtime Phish soundman Paul Languedoc during his 12-step program. Of note, he mentioned that Phish’s first tours after their 2009 reunion took place while he was still on probation and that he had to submit his tour routing, hotel accommodations and other travel plans in advance.

Stern and Anastasio both gave credit to Dr. John Sarno whose book Healing Back Pain helped the guitarist when he was struggling physically and under immense pressure to put together Phish’s Baker’s Dozen run in 2017.

A 90-minute version of the interview with air on HBO Max this Thursday.