20. The Incredible String Band
Graphic House/Archive Photos/Getty ImagesThe Incredible String Band found themselves out of sync with the Woodstock crowd’s mood for heavier rock, playing on Saturday evening after Santana and Keef Hartley Band. Despite their pleasant, unique sound, blending folk with world and psychedelic elements — it was a quieter acoustic set in a festival that demanded a faster pace, heavier sound. Scheduled for a Friday performance, they delayed to Saturday due to rain, perhaps missing a potentially more receptive audience. Their set featuring unreleased songs from upcoming albums showcased their creativity and talent regardless of missing the mark with the crowd.
19. Johnny Winter
Gai Terrell/Redferns/Getty ImagesLegendary Texas blues singer delivered a powerful performance at Woodstock, starting at midnight between Sunday and Monday. With a set that spanned 65 minutes, Winter showcased his exceptional electric blues, slide guitar, and solos. His set included both original compositions like “Leland Mississippi Blues” and “Mean Town Blues” and covers from blues and rock’n’roll giants such as B.B. King’s “You Done Lost Your Good Thing Now” and Chuck Berry’s “Johnny B. Goode.” Accompanied by his brother Edgar Winter on several tracks, Winter’s set added a jazzier sound to the Woodstock lineup.
18. Mountain
Archive Photos/Hulton Archive/Getty ImagesMountain played their fourth-ever gig at Woodstock on August 16, 1969. Their performance, in front of 500,000 people around 9:00 pm, included their opener “Blood of the Sun” and a memorable rendition of “Stormy Monday”. They also performed “Theme for an Imaginary Western”, a song written by Pete Brown and Jack Bruce of Cream — a band they’re said to be heavily influenced by. Their set showcased Leslie West’s guitar solos, particularly after “Dreams of Milk and Honey”. “For Yasgur’s Farm”, another highlight, captured the essence of the event. The band would soon see changes, with drummer Norman Smart being replaced by Corky Laing shortly after.
17. Arlo Guthrie
David Fenton/Getty ImagesArlo Guthrie, son of the legendary Woody Guthrie, took to the Woodstock stage early on Saturday morning amidst rain, delivering a performance while clearly under a state of intoxication. Despite the challenging conditions with a wet stage, the performance, particularly highlighted by his song “Coming into Los Angeles,” managed to thrill the audience. Guthrie’s set, though brief and veiled in a psychedelic haze, remains memorable for its humor and the spirited rendition of “Walkin’ Down the Line,” punctuated by his comedic announcement about the New York State Thruway and “Lotta freaks!”
16. Joan Baez
Fotos International/Getty ImagesJoan Baez, often seen as the female counterpart to Bob Dylan, closed the first day of Woodstock around 3:00 am. Known for her folksinging and anti-war activism, Baez’s set, performed under light drizzle that escalated to heavy rain after her performance, featured a blend of beautifully arranged songs showcasing her exquisite voice. Highlights included a mix of gospel, folk, and songs of protest, reflecting the era’s social and political unrest. Her performance provided a tranquil yet poignant end to the festival’s chaotic first day, leaving a lasting impression on the Woodstock audience.
15. Canned Heat
Warner Bros/Michael Ochs Archives/Getty ImagesCanned Heat’s Woodstock performance had an expertly chosen setlist, including hits like “Going Up The Country” and “On The Road Again,” with the latter serving as an encore. Their set featured a nearly 30-minute jam on “Woodstock Boogie,” showcasing their unique blend of heavy, gritty blues. Notably, their rendition of “A Change Is Gonna Come,” a song seldom recorded, captured the festival’s communal spirit, as seen when singer Bob Hite shared a cigarette with a fan who climbed on stage. This performance was among the first for new guitarist Harvey Mandel, following a lineup change just days before the festival.
14. Ten Years After
Jorgen Angel/RedfernsTen Years After, a British band known for their heavy blues rock, unfortunately experienced technical difficulties during their Woodstock performance due to high humidity, causing their instruments to go out of tune. Despite these issues, their final song “I’m Going Home” became one of the festival’s highlights, showcasing the virtuosity of guitarist Alvin Lee. This intense performance, featuring a fast guitar riff and solos including a medley of classic rock’n’roll songs, was the only part of their set captured on film due to the recording and equipment failures.
13. The Band
Michael Ochs Archives/Getty ImagesThe Band, predominantly Canadian, performed at Woodstock on August 17th around 10 pm with an exceptional Folk-Rock performance, with a reception that surpassed US-based folk bands. They played a set deeply rooted in the genre, influenced by Bob Dylan, their former mentor. Highlights included “I Shall Be Released” and “The Weight,” perfectly exemplifying their Folk-Rock sound. Despite having only one album at the time, Music From Big Pink, their performance was memorable, including seven songs from the album and concluding with “The Weight,” famously featured in “Easy Rider.”
12. Grateful Dead
Larry Hulst/Michael Ochs Archives/Getty ImagesThe Grateful Dead’s Woodstock performance was plagued by technical issues, even leading to electrical shocks for the band members. This significantly impacted their set, ultimately resulting in an atypical show from what was considered one of the best live bands of the time. Their performance featured a notably long version of “Turn On Your Lovelight,” lasting nearly 38 minutes, during which an audience member interrupted with a speech. Despite the challenges, a clean soundboard recording of the show exists, though it has never been officially released due to the performance’s quality.
11. Richie Havens
Paul DeMaria/NY Daily News Archive via Getty ImagesGranted the honor of being the opening act at Woodstock, Richie Havens initially planned to play four songs. But, they ended up performing longer due to audience demand and logistical delays. He claimed to have played every song he knew over approximately 2 hours and 45 minutes. Notably, he improvised “Freedom” on stage, captivating the audience with spontaneity. Havens’ set included a mix of his own material and covers, including Beatles songs, even though he humorously struggled with some lyrics. His performance, particularly the improvised “Freedom,” became a memorable standout moment of the festival.
10. Country Joe McDonald
Michael Ochs Archives/Getty ImagesCountry Joe McDonald’s memorable solo performance at Woodstock, distinct from his work with The Fish, could be summed up as a humorous call to protest. He played a relaxed set including the infamous “Fish” Cheer, famously spelling out F-*-*-K, leading into the anti-Vietnam anthem “I-Feel-Like-I’m-Fixin’-To-Die Rag.” His performance, filled with engaging songs and a direct call to action, underscored the festival’s spirit of peace and music, making a lasting impact with his mix of satirical wit and earnest commentary on the Vietnam War.
9. Jefferson Airplane
Getty Images/Getty ImagesBy this point, Jefferson Airplane was now one of the most well-known bands in America. Their performance at Woodstock was equally monumental, essentially marking the dawn of a new era in rock music. They seamlessly brought their signature blend of psychedelic and blues rock to the festival. Introduced by Grace Slick as “morning maniac music,” they lived up to the title with a set that included hits like “Somebody to Love” and “White Rabbit.” Their performance, especially the song “Volunteers,” became an anthem for the cultural and social revolution of the time.
8. Joe Cocker
Fotos International/Getty ImagesJoe Cocker’s Woodstock performance, particularly his rendition of “With a Little Help from My Friends,” marked a defining moment in his career and became a highlight of the festival. Cocker wasn’t widely famous before Woodstock, but quickly became known for his soulful voice and the Grease Band’s excellent backing. His energetic performance and unique interpretation of the Beatles’ classic catapulted him into fame. Unfortunately, a heavy thunderstorm followed his set, pausing the festival for hours. Cocker’s performance remains a memorable part of Woodstock’s legacy.
7. Sly and the Family Stone
Warner Bros/Michael Ochs Archives/Getty ImagesReportedly taking the stage at 3:30 AM on Sunday, Sly & The Family Stone delivered an electrifying performance at Woodstock. Their music, a pioneering mix of funk-rock, soul, R&B, psychedelic elements, and gospel, was groundbreaking for its diversity in both the band’s makeup and sound. Despite their late appearance, the band’s energy and freshness brought renewed life to the festival, making this show one of their most memorable performances. Their setlist was heavily drawn from their hit album Stand! and included extended versions of “Music Lover” and “I Want To Take You Higher.”
6. Crosby, Stills, Nash & Young
Robert Altman/Michael Ochs Archives/Getty ImagesHaving just formed and released their debut album in May 1969, Crosby, Stills, Nash & Young, performed at Woodstock as their second live appearance. Stephen Stills acknowledged their nervousness to the audience during their early morning set. They played both acoustic and electric sets, with Neil Young requesting not to be filmed, leading to his exclusion from the documentary and soundtrack. This performance remains a significant moment in their early history as a group.
5. Janis Joplin
Malcolm Lubliner/Michael Ochs Archives/Getty ImagesJanis Joplin’s Woodstock performance, though occurring late on Saturday into Sunday around 2:00 am and perhaps lacking some of her usual power, remains a significant snapshot of her tragically short career. Accompanied by a full ensemble, Joplin delivered a set that mostly featured tracks from her solo album I Got Dem Ol’ Kozmic Blues Again Mama! The set included standout covers like “Raise Your Hand” by Eddie Floyd and “Summertime,” showcasing her unique blend of rock and soul. Despite the challenges of her late slot, Joplin’s performance is celebrated today.
4. Creedence Clearwater Revival
Tucker Ranson/Pictorial Parade/Archive Photos/Getty ImagesCreedence Clearwater Revival was arguably the stars of the show. Starting late at night due to The Grateful Dead’s extended set, they played their catchy blend of R&B, Folk, and country rock. Despite John Fogerty’s concerns that many in the audience had ended up falling asleep, their legendary set included hits like “Born on the Bayou,” “Bad Moon Rising,” and “Proud Mary.” Their music, characterized by tight, energetic performances, was a highlight, culminating in extended jams on “I Put a Spell on You” and “Suzie Q.”
3. Santana
Tucker Ransom/Hulton Archive/Getty ImagesSantana brought the heat to Woodstock. Their unique Latin rock fusion effectively captivated an audience largely unfamiliar with their work. Their set included tracks from their debut album, delivering both powerful and magical renditions. Particularly memorable was “Soul Sacrifice,” featuring an exceptional drum solo. Carlos Santana, despite claiming to have been under the influence of LSD and hallucinating during the performance, played flawlessly. Managed by the legendary Bill Graham, their appearance at Woodstock marked the beginning of Santana’s rise to fame, leaving a lasting impact on the festival’s legacy.
2. The Who
Michael Putland/Getty ImagesWith The Who scheduled to play second-to-last before Jefferson Airplane, their set kicked off in the early hours of Sunday morning at around 5:00 am. They performed their iconic Tommy album, a rock opera narrating the story of a “deaf, dumb, and blind” boy’s challenging life and eventual rise to fame. The performance, culminating with the sunrise at 6:05 am, was both powerful and captivating, despite being shorter than their usual sets from the 1969 tour. The set was highlighted by the ritual guitar smashing by Pete Townshend, marking a memorable conclusion to Woodstock.
1. Jimi Hendrix
Feddersen/ullstein bild via Getty ImagesJimi Hendrix was scheduled to be the final act on Sunday at Woodstock, but due to delays, he performed on Monday at 9:00 am to a somewhat dwindled crowd. Despite this, Hendrix’s set was nothing short of magical and included a mix of well-known Experience songs and new material with his band Gypsy Sun & Rainbows. His extended performance of “Purple Haze” before breaking out into incredible guitar solos was a standout moment. Despite the technical challenges and the band’s new formation limiting rehearsal time, Hendrix’s performance, particularly his rendition of “The Star-Spangled Banner,” became emblematic of Woodstock, perfectly captivating the anti-war sentiment
