Courtesy of the James Taylor official website.

Singer-songwriter and musical icon James Taylor kicked off the first of two nights at the Santa Barbara Bowl on May 13, with a soundtrack centering travel, family and pure musical connection. 

Perhaps no other musician has the score of accolades and the cultural influence that Taylor has garnered in his over 50-year career. The singer-songwriter remains the only artist to have both a number one album in six different decades and received the Presidential Medal of Freedom in 2015. Taylor is even the namesake for one of the world’s most famous pop stars. 

Fans flocked to the Bowl hours before Taylor took to the stage, with many bringing along younger family members to experience the work of one of music’s most influential members. 

Opening act and folk trio Tiny Habits took to the stage for a brief, half-hour performance, ultimately winning the Bowl over with their harmonies, banter and descriptive, story-like lyrics. A trio that met at Berklee College of Music, the group released their first album “All For Something” in 2024, and recently opened for Gracie Abrams on her sold-out 2023 tour — an audience that is radically different from the following that Taylor has gained throughout the decades. 

“This feels like a family event — shoutout to all the parents and grandparents that are here,” the band joked, referencing the age difference between themselves and the majority of the Bowl’s crowd. Their quip was met with elation and cheers, with some in the crowd even waving the band’s merch and shouting back. 

The choice to perform a cover of Fleetwood Mac’s “Landslide” successfully won the crowd over, with many recognizing the track from its first melancholic notes. The influence of music released throughout the 1960s and ‘70s could certainly be felt in Tiny Habits’ performance.  The band expressed great appreciation for being given the opportunity to open for Taylor, along with still lingering surprise. 

“It never gets old,” the trio shared with the crowd. “That’s literally James Taylor. And why are we here? But, we’re here.”

Less than half an hour later, Taylor took to the stage alongside his Summer 2025 All-Star Band, a group of 11 accomplished musicians with years of musical experience. Notable members include Dorian Holley, who served as a backing vocalist for musical powerhouses Michael Jackson, Aretha Franklin and Whitney Houston, and Taylor’s own son, fellow vocalist Henry Taylor. Receiving a special shoutout was Lou Marini, a saxophonist for Saturday Night Live’s inaugural band who spent the night celebrating his 80th birthday alongside the Santa Barbara Bowl audience. 

Before launching into the first song of the night, Taylor took a few moments to take in the crowd and briefly acknowledged his return to the venue. Taylor is no stranger to the Santa Barbara Bowl, having played at the venue eight times before. 

“Back at the Bowl!” Taylor noted before starting a fast-paced night that covered over 50 years of material. Beginning with 1975’s “Wandering,” he took a moment to introduce the night’s theme of traveling and exploration. 

“We put together a string of traveling songs because we got a lot of them,” Taylor joked. “If you write songs about what you do and what you do is travel, that’s what you’re gonna get.” 

Not only did songs like “Walking Man,” “Stretch of the Highway” and “My Traveling Star” further reflect Taylor’s decades of travel and experience as an accomplished musician, but visuals featuring photos of Taylor, his bandmates and their travels across the United States and world only added to the theme of the night, and were just some of many reminders of the longevity of Taylor’s career. 

Beginning in 1968 with the appropriately named “James Taylor” album, the singer spoke briefly on the creation of what would become his first signature track and the help he received from his mentors at the time, who happened to be the four most famous musicians in the world. 

“I was a huge Beatles fan and they had just signed me to their brand new label. I couldn’t believe my luck,” Taylor recalled. He spoke briefly about how the band assisted him with creating and recording his first album while working on their own self-titled piece, which would become more famously known as the “White Album.” While having a rare day alone,  Taylor recalled that he experienced a “deep mood of homesickness,” which would ultimately lead to the creation of his first lead single, “Carolina in My Mind.”

Taylor’s setlist made sure to also reference his worldwide adventures, with the inclusion of “Only a Dream in Rio,” a song that he penned after witnessing the reactions to the 1985 Argentine elections firsthand. “Mexico,” an obvious Taylor staple, was also played, with the live rendition featuring an electric guitar, trumpets and a bongo solo. 

One of the most memorable and personal moments occurred early in the night, with Taylor sharing a story about his late father supporting him through the breakup of his first band and struggles with drug abuse. 

“I think he might have saved my life,” Taylor admitted, a moment of honesty and vulnerability that left many in the Bowl emotional. He explained that his 1997 song “Jump Up Behind Me” was about the time his father drove hours to comfort Taylor after the singer alluded to his difficulties in a phone call. 

“Mom’s gotta be there all the time … but you can make a decent father out of just a couple of stories,” Taylor joked before launching into the performance. The singer-songwriter frequently cracked jokes throughout the night, bantering with the Bowl and responding to fans’ comments. After removing his jacket halfway through the night to elated cheers, Taylor threatened to remove his teeth next and told a fan expressing her adoration that it“helped that [he] doesn’t know her.”

The performance of “Sweet Baby James,” another Taylor classic, was also sprinkled with his wit and charm. He explained that “Baby James” was actually written about his nephew, who his brother named after him. Despite labeling the choice as a “moment of relapsed judgement,” Taylor took a moment to acknowledge his nephew, who he happily declared turned out great (although Taylor did admit to the crowd that he was, “amazed they let him keep [the name]”).

A more intimate and quiet moment came when Taylor performed perhaps his most famous and tragic track, “Fire and Rain.” Not addressing the crowd at the song’s beginning or end, Taylor was accompanied by a violin performance, making an already devastating song much more somber. Accompanied by many softly signing along in the crowd, the moment served as another reminder of Taylor’s skill when it comes to bringing audiences together through shared experiences and emotions. 

Another classic performed was “You’ve Got a Friend,” a cover of the original song by Carole King — one of three covers played. Taylor also performed his cover of “How Sweet It Is (To Be Loved by You)” from the late, great Marvin Gaye, an encore choice that managed to get the crowd up and moving as the clock ticked closer to the Bowl’s 10 p.m. curfew. 

Toward the conclusion of his time at the Santa Barbara Bowl, Taylor took a moment to thank the crowd for their participation and praised the venue, describing it as an “unparalleled place.” 

“I don’t know when we’ll be back, but I hope it will be soon,” Taylor expressed to a crowd still clamoring for one more song. 

Initially appearing to exit the stage, Taylor requested the audience for one more song — a duet with his son and backing vocalist Henry Taylor. The simple setup of a single guitar and father-son harmony became the standout moment of the night; a beautiful performance that brought generations together, like Taylor’s music has continued to do throughout the years.