It’s August 14, 1943. A Saturday night at the Hollywood Bowl. While the crowd has just been wowed by the Los Angeles Philharmonic’s performance of music from Fantasia, they are anxious for what’s next. There are 10,000 people in attendance—a sellout crowd, though the anticipation, so thick it seems to be dripping from the trees that surround the amphitheater, makes it feel like many more. Finally, the moment arrives. A young heartthrob named Frank Sinatra takes the stage to sing with the orchestra. The next day, the Los Angeles Times will report that there were “hysterical screams, pleading, sighs, whistles, endearments, gasps, agonized cries.” He sings “Dancing in the Dark,” “The Song Is You,” and “You’ll Never Know,” while “10,000 slick chicks” and “breathless babies in bobby socks” (according to the Times) collectively lose their minds. It is the first time a pop star has played their music with an orchestra at the Hollywood Bowl. It will not be the last. 

For a nonclassical musician, performing with an orchestra doesn’t simply add a veneer of sophistication to otherwise straightforward songs. These concerts present unique challenges for artists more accustomed to the spontaneity and kinetic energy of live pop, rock, or hip-hop. But the rewards can be staggering. Like an art restorer cleaning a painting, orchestras highlight depths and colors in the music that might otherwise be difficult to experience. The lovelorn blues of a tear-jerking ballad might now have the heavy sadness of a stormy day. The relentless drive of a fist-pumping anthem now gallops to a dramatic crescendo.  

While Sinatra was the first to sing his hits at the Bowl accompanied by an orchestra, he technically wasn’t the first pop singer to appear with an orchestra on the Bowl’s stage; in 1937, as part of a memorial concert for George Gershwin, Fred Astaire joined the LA Phil to sing “They Can’t Take That Away from Me” from Shall We Dance. But Sinatra’s appearance was unusual enough to cause controversy. The Bowl at that time was still seen as the sophisticated outdoor home of Western art music—classical music, in other words, that some felt might be sullied by the appearance of other types of artists. Sinatra and the Los Angeles Philharmonic were aware of this and tried to mitigate it: Despite performing his own music, Sinatra was billed in the night’s program as a “baritone soloist.” 

It would take a little over a decade for the experiment to be repeated. This time, in 1954, Nat King Cole became the first Black pop star to sing at the Bowl, performing with the Hollywood Bowl Pops—a forerunner of today’s Hollywood Bowl Orchestra. Cole’s response to the evening was noticeably different from Sinatra’s; he was conscious of the honor but didn’t feel the need to downplay his appearance: “Only a few years ago I was a struggling entertainer around Hollywood. Now, due to good fortune, I am getting the best presentation possible. It is like a wonderful dream come true.”  

Cole’s concert opened the door to a number of jazz singers who would perform with an orchestra at the Bowl in coming years. Peggy Lee made her first appearance, while Ella Fitzgerald debuted in 1960, playing her first of many Bowl concerts. Sarah Vaughan later repeated Astaire’s trick, singing Gershwin with Michael Tilson Thomas and the LA Phil, as well as her own jazz combo, in 1974. Billie Holiday performed in 1953; 26 years later, Nina Simone paid her tribute in one of Simone’s several Hollywood Bowl concerts. It’s a tradition that continues today, with artists like Tony Bennett and Lady Gaga (2017) and Laufey (2024) carrying the tradition of jazz vocalists into the 21st century. 

But not every artist who plays with an orchestra is a crooner. A year after the release of their 1969 album Concerto for Group and Orchestra with the Royal Philharmonic Orchestra, heavy-metal progenitors Deep Purple became the first rock band to play with an orchestra here, teaming up with the Los Angeles Philharmonic. Procol Harum’s baroque-influenced prog-rock made them a natural fit in 1973 (as did the bit of Bach they lifted for their hit “A Whiter Shade of Pale”). During World Cup Week in 1994, Garth Brooks performed a special solo acoustic show at the height of his popularity, backed by the Hollywood Bowl Orchestra.  

In recent years, everyone from Beck to Death Cab for Cutie to Rodrigo y Gabriela has linked up with the LA Phil at the Hollywood Bowl. Both Billie Eilish and Laufey have released concert films shot on the Bowl’s stage with the LA Phil. And as for spontaneity? No less an improviser than Phish’s Trey Anastasio played solo with the orchestra in 2014 (they turned in a pretty sick “You Enjoy Myself,” according to phans who were there).  

It's no longer considered a novelty for even the wildest artist to appear on an orchestra’s stage: Flying Lotus’ glitchy, psychedelic electronic show in 2021 made sure of that, and 2025’s King Gizzard and the Lizard Wizard show should kill any lingering doubts. But in a thrilling reversal, classical music now finds itself in places that were once pop’s sole domain. Sometimes it means setlists comprising purely orchestral renditions of canonical pop music, as when producer George Martin conducted a Beatles tribute at the Bowl in 1999. But it also means that this past spring, the LA Phil led by Music & Artistic Director Gustavo Dudamel did something no major orchestra had done before, playing a set at Coachella, the world’s most prestigious pop music festival. Joined by Laufey, LL Cool J, Cynthia Erivo, Dave Grohl, and others, they presented orchestrated versions of those artists’ songs, as one might expect. But they also performed music by Stravinsky, Wagner, Bach, and more, to the delight of a raucous crowd that chanted the orchestra and Gustavo Dudamel’s names. In the desert dusk, it seemed as though the line between classical and pop music—a line the LA Phil, the Hollywood Bowl Orchestra, and countless artists had crossed over time and time again—was fully erased.