After Hendrix disbanded the Jimi Hendrix Experience in mid-1969, he formed the group he called Gypsy Sun and Rainbows ostensibly to fulfill the contract of the "Jimi Hendrix Experience" to play Woodstock. Bassist Billy Cox had already been rehearsing and playing with Hendrix since April, but the band was short-lived. With Cox and his drummer friend Buddy Miles, he next formed the Band of Gypsys, this time to fulfill his legal (US only) obligation to produce an LP of new material for Ed Chalpin, to be released on the Capitol label, which Hendrix, in an interview as early as March, had already mentioned was going to be a "jam" album titled "Band of Gypsys." The name "Band of Gypsys" was also mentioned as an alternative name for the group by Hendrix in his introduction during the Woodstock concert. With these musician friends he further consolidated his new musical style that he had tentatively begun in the last days of the "Jimi Hendrix Experience" and had largely developed with GS&R. They recorded a single "Stepping Stone" b/w "Izabella" for Reprise (quickly withdrawn after its release), some studio material, and several finished tracks towards his forthcoming LP, some of which have been posthumously released on First Rays of the New Rising Sun and elsewhere. They made their live debut at the Fillmore East on New Year's Eve, 1969, for a series of four shows spread over two nights.
The Fillmore East concerts featured mostly new songs, as the songs Hendrix would have to select for the Band of Gypsys LP had to be, as this was a condition of the judgment against him. The fact that these songs were never properly released as studio versions elevates the significance of this album. (Studio versions of "Message of Love" and "Power of Soul" are available on some posthumous releases.) The version of "Machine Gun" from this show contains improvised sections featuring guitar feedback and percussive effects that have commonly been seen as a simulation of the sounds of war such as explosions, falling bombs and most prominently, the titular machine guns. This performance was captured on hand held portable B&W video recorders. 
Hendrix selected two Buddy Miles songs and only three of his own for the album as a damage limitation exercise, obviously not wanting to give away any more of his new songs than he had to, as he would personally receive nothing for the album. He later spoke of the sub-standard quality of the LP, no doubt hoping to limit its sales. "We Gotta Live Together" is heavily edited to fit on the album. Its original length is about twice that which can be heard on the album. A longer version can be heard on the 2-disc Live at the Fillmore East album; the full version has never been officially released.
Due to the demands of four sets over two days, the band faced a lack of material. So, Hendrix did rely on Experience-era favourites "Wild Thing," "Hey Joe," "Purple Haze, "Voodoo Child (Slight Return)," "Foxy Lady," "Fire," and "Stone Free" to fill out the sets, not included on the original album. In fact, nearing the end of the fourth set, Hendrix said, "We're just trying to figure out something to play, but we only know about six songs right now...seven...nine." He then launched into a version of "Voodoo Child (Slight Return)." "Foxy Lady" was included on the later Japanese/German re-release (details below). Further, "Wild Thing," "Voodoo Child (Slight Return)" and "Stone Free" can be heard on the MCA/Experience Hendrix Live at the Filimore East 2-disc set. 
After a disastrous show at Madison Square Garden on January 28, where he crudely insulted a woman in the audience, only played two songs and then left the stage, Band of Gypsys was disbanded. With Experience member Mitch Mitchell on drums and Billy Cox on bass, The Jimi Hendrix Experience was reformed and for the next several months would work on Hendrix's next album, projected to be a double (or even triple) album until the leader's tragically sudden death that September. He had also been due to work with jazz composer and Miles Davis collaborator Gil Evans, and apparently numerous other projects yet to be initiated, including those with Eric Clapton, Emerson Lake and Palmer, Miles Davis, and Duane Allman. 
Produced by Hendrix (as "production company" "Heaven Research", no doubt to get the producer's fee), Band of Gypsys reached #5 in the U.S. and #6 in the UK and became one of the artist's best-selling albums. In certain foreign markets, including the UK, the album was originally released with an alternative cover photograph which featured dolls of Hendrix, Brian Jones, Bob Dylan and British DJ John Peel, an early supporter of Hendrix.
Band of Gypsys is also the name of a DVD documentary concerning the album and Hendrix's performances at the Fillmore during New Year's Eve 1969, and New Year's Day 1970. It contains the B&W footage.((youtube id="kK97og3tDzY&feature=related"))((/youtube))