By August 1969, when Jefferson Airplane performed "The Ballad of You & Me & Pooneil" at the Woodstock Festival, they were experiencing significant success and acclaim, following the release of their iconic album *Surrealistic Pillow* in 1967. This album featured hit singles like "Somebody to Love" and "White Rabbit," which helped solidify their place in the psychedelic rock movement. Just prior to Woodstock, they had released *Volunteers* in 1969, which reflected the band's evolving political message and countercultural ethos. The performance at Woodstock not only marked a pinnacle of their live exposure but also demonstrated their commitment to the anti-establishment sentiments of the time, with the song embodying themes of unity and revolution. This event, along with their participation in the festival, further elevated their status as a leading force in the counterculture movement.