Hendrix was advertised to play the Woodstock Music Festival, along with many of the other biggest rock groups of the time. It was to take place on rented farmland in Upper State New York from August 15-18, 1969. Although Hendrix’s music had been written for a power trio of guitar, bass, and drums, he wanted to expand his sound so he added rhythm guitarist Larry Lee (another old friend from his R&B days), and Juma Sultan and Jerry Velez to play congas. After drummer Mitch Mitchell arrived, this new lineup rehearsed for less than two weeks before the festival and according to Mitchell never really meshed. In addition, although Woodstock would become famous and mythologized through the documentary film of the same name, by the time of his performance, Hendrix had been up for three days, and his band was short on sleep as well, contributing a rawness to their filmed performance.
Before Hendrix even arrived at the festival he started to hear media reports that the crowds of kids showing up for the festival were swelling to biblical proportions, in addition to the emerging logistical problems being reported at the site. This gave Hendrix pause for concern since he did not like performing in front of very large crowds.  Since he was considered an important draw for the festival, and because of his manager’s negotiations, Hendrix was getting paid more than the other performers, ($18,000, plus $12,000 for rights to film him). As the scheduled time slot of Sunday night at midnight drew closer, Hendrix indicated that he would rather wait and close the show. A substantial rainstorm that day had delayed the schedule of performers, so when Hendrix insisted on being the closing headliner, it pushed back the time when they finally hit the stage – which ended up being 8:30am Monday morning. The audience which had peaked at an estimated 400,000 people during the festival, was now reduced to about 30-40,000 by that point; many of whom merely waited to catch a glimpse of Hendrix before leaving during his show. This reflected the reality that by the third day attendees had been sleeping in muddy conditions with limited food.
Hendrix and his band were introduced by the festival MC, Chip Monck, as “The Jimi Hendrix Experience,” but once on stage Hendrix clarified saying, “We decided to change the whole thing around and call it ‘Gypsy Sun and Rainbows.’ For short, it’s nothin but a ‘Band of Gypsys.'” He then launched into a two hour set, the longest of his career. Hendrix started off with a new song, “Message to Love.” (His Woodstock set consisting of new material, along with his well-known hits).
Hendrix’s psychedelic rendition of the U.S. national anthem, “The Star-Spangled Banner” occurred about 3/4 into their set, (after which he morphed into “Purple Haze”). The song had actually been part of his set for a year and he had already performed it on at least three different occasions. During the number, Hendrix used feedback and sustain on his guitar to recreate the sound of wails and falling rockets. Although pundits quickly branded the song as a political manifesto against the Vietnam War, Hendrix himself never explained its meaning other than to say at a press conference three weeks later, “We’re all Americans. . .it was like ‘Go America!’. . .We play it the way the air is in America today. The air is slightly static, see.” Whatever Hendrix’s motivation, “the song became part of the sixties Zeitgeist” as it was captured forever in the Woodstock film. Hendrix’s iconic image performing this number wearing a blue-beaded white leather jacket with fringe and a red head scarf, has since been regarded as a defining moment of the 1960’s.
Hendrix performed “Hey Joe” as the encore to finish off their set which concluded the 3 and ½ day Woodstock Music Festival. Upon leaving the stage Hendrix collapsed from exhaustion.
After Woodstock, this particular lineup of the band appeared on only two more occasions. The first was a street benefit in Harlem where, in a scenario similar to the festival, most of the audience had left and only a fraction remained by the time Hendrix took the stage. Within seconds of Hendrix arriving at the site two youths had stolen his guitar from the back seat of his car, although it was later recovered. The band’s only other appearance was at the Salvation club in Greenwich Village, New York. After some studio recordings, Hendrix disbanded the group. Some of this band’s recordings can be heard on the MCA Records box set The Jimi Hendrix Experience and on South Saturn Delta. Their final work together was a session on September 6. Hendrix’s September 9 appearance on TV’s The Dick Cavett Show, backed by Cox, Mitchell and Juma Sultan, was credited as the “Jimi Hendrix Experience”.