The corner of Haight and Ashbury, center of the San Francisco neighborhood in which the Grateful Dead shared a house at 710 Ashbury, fall 1966 to spring 1968. Garcia served as lead guitarist, as well as one of the principal vocalists and songwriters of the Grateful Dead for their entire career. Garcia composed such songs as "Dark Star", "Franklin's Tower", and "Scarlet Begonias", among many others. Robert Hunter, an ardent collaborator with the band, wrote the lyrics to all but a few of Garcia's songs.
Garcia was well-noted for his "soulful extended guitar improvisations", which would frequently feature interplay between himself and his fellow band members. His fame, as well as the band's, arguably rested on their ability to never play a song the same way twice. Often, Garcia would take cues from rhythm guitarist Bob Weir on when to solo, remarking that "there are some [...] kinds of ideas that would really throw me if I had to create a harmonic bridge between all the things going on rhythmically with two drums and Phil [Lesh's] innovative bass playing. Weir's ability to solve that sort of problem is extraordinary. [...] Harmonically, I take a lot of my solo cues from Bob."
When asked to describe his approach to soloing, Garcia commented: "It keeps on changing. I still basically revolve around the melody and the way it’s broken up into phrases as I perceive them. With most solos, I tend to play something that phrases the way the melody does; my phrases may be more dense or have different value, but they’ll occur in the same places in the song. [...]"
Garcia and the band toured almost constantly from their formation in 1965 until Garcia's death in 1995, a stint which gave credit to the name "endless tour". Periodically, there were breaks due to exhaustion or health problems, often due to unstable health and/or Garcia's drug use. During their three decade span, the Grateful Dead played 2,314 shows.
Garcia's mature guitar-playing melded elements from the various kinds of music that had enthralled him. Echoes of bluegrass playing (such as Arthur Smith and Doc Watson) could be heard. But the "roots music" behind bluegrass had its influence, too, and melodic riffs from Celtic fiddle jigs can be distinguished. There was also early rock (like Lonnie Mack, James Burton and Chuck Berry), contemporary blues (such as Freddie King and Lowell Fulson), country and western (such as Roy Nichols and Don Rich), and jazz (like Charlie Christian and Django Reinhardt ) to be heard in Jerry's style. Don Rich was the sparkling country guitar player in Buck Owens's "the Buckaroos" band of the 1960s, but besides Rich's style, both Garcia's pedal steel guitar playing (on Grateful Dead records and others) and his standard electric guitar work, were influenced by another of Owens's Buckaroos of that time, pedal-steel player Tom Brumley. And as an improvisational soloist, John Coltrane was one of his greatest personal and musical influences.
Garcia later described his playing style as having "descended from barroom rock and roll, country guitar. Just 'cause that's where all my stuff comes from. It's like that blues instrumental stuff that was happening in the late Fifties and early Sixties, like Freddie King." Garcia's style varied somewhat according to the song or instrumental to which he was contributing. His playing had a number of so-called "signatures" and, in his work through the years with the Grateful Dead, one of these was lead lines making much use of rhythmic triplets (examples include the songs "Good Morning Little School Girl", "New Speedway Boogie", "Brokedown Palace", "Deal", "Loser", "Truckin'", "That's It for the Other One", "U.S. Blues", "Sugaree", and "Don't Ease Me In").
Garcia played many guitars during his career, which ranged from Fender Stratocasters and Gibson SGs to custom-made instruments. During his thirty-odd years of being a musician, Garcia used about twenty-five different guitars.
In 1965, when Garcia was playing with the Warlocks, he used a Guild Starfire, which he also used on the début album of the Grateful Dead. Beginning in late 1967 and ending in 1968, Garcia played various colored Gibson Les Paul guitars. In 1969, he picked up the Gibson SG and used it for most of that year and 1970, except for a small period in between where he used a Sunburst Fender Stratocaster.
During Garcia's "pedal steel flirtation period" (as Bob Weir referred to it in Anthem to Beauty), from approximately 1968 to 1973, he played a ZB Custom D-10 steel guitar, especially in his earlier public performances. Although this was a double neck guitar, Garcia often would choose not to attach the last 5 pedal rods for the rear or Western Swing neck. Additionally, he was playing an Emmons D-10 at the time of the Grateful Dead's and New Riders of the Purple Sage's final appearances at the Filmore East in late April 1971. Also, he had been given a Fender Pedal Steel (probably a 1000 model) prior to owning the ZB Custom, but did not play it much.
In 1969, Garcia played pedal steel on two notable outside recordings: the track "The Farm" on the Jefferson Airplane album Volunteers; and the hit single "Teach Your Children" by Crosby, Stills, Nash & Young from their album Déjà Vu, released in 1970. Garcia played on the latter album in exchange for harmony lessons for the Grateful Dead, who were at the time recording their acoustic albums Workingman's Dead and American Beauty.
In 1972, Garcia used a Fender Stratocaster nicknamed Alligator for its alligator sticker on the pickguard. The guitar was given to him by Graham Nash. This was due in part to damage to his first custom-made guitar, made by Alembic. This guitar, nicknamed Wolf for a memorable sticker Garcia added below the tailpiece, cost $1500 - extremely high for the time
In the late eighties Garcia, Weir and CSN (along with many others) endorsed Alvarez Yairi acoustic guitars. There are many photographs circulating (mostly promotional) of Jerry playing a DY99 Virtuoso Custom with a Modulus Graphite neck. He opted to play with the less decorated model but the promotional photo from the Alvarez Yairi catalog has him holding the "tree of life" model. This hand-built guitar was notable for the collaboration between Japanese luthier Kazuo Yairi and Modulus Graphite of San Rafael. As with most things Garcia, with his passing, the DY99 model is rendered legend and valuable among collectors.
Wolf was made with an ebony fingerboard and featured numerous embellishments like alternating grain designs in the headstock, ivory inlays, and fret marker dots made of sterling silver. The body was composed of western maple wood which had a core of purpleheart. Garcia later had former Alembic employee Doug Irwin replace the electronics inside the guitar, at which point he added his own logo to the headstock alongside the Alembic logo. The system included two interchangeable plates for configuring pickups: one was made for strictly single coils, while the other accommodated humbuckers. Shortly after receiving the modified instrument, Garcia requested another custom guitar from Irwin with the advice "don't hold back."
During the Grateful Dead's European Tour, Wolf was dropped on several occasions, one of which caused a minor crack in the headstock. Garcia returned it to Irwin to fix; during its two-year absence Garcia played predominantly Travis Bean guitars. On September 28, 1977, Irwin delivered the renovated Wolf back to Garcia. The wolf sticker which gave the guitar its name had now been inlaid into the instrument; it also featured an effects loop between the pick-ups and controls (so inline effects would "see" the same signal at all times) which was bypassable. Irwin also put a new face on the headstock with only his logo (he later claimed to have built the guitar himself, though pictures through time clearly show the progression of logos, from Alembic, to Alembic & Irwin, to only Irwin).
Nearly seven years after he first requested it, Garcia received his second custom guitar from Irwin in 1979. It was named Tiger from the inlay on the preamp cover. The body of Tiger was of rich quality: the top layer was cocobolo, with the preceding layers being maple stripe, vermilion, and flame maple, in that order. The neck was made of western maple with an ebony fingerboard. The pickups consisted of a single coil DiMarzio SDS-1 and two humbucker DiMarzio Super IIs which were easily removable due to Garcia's preference for replacing his pickups every year or two. The electronics were composed of an effects bypass loop, which allowed Garcia to control the sound of his effects through the tone controls, and an amplifier which rested behind a plate in the back of the guitar. In terms of weight, everything included made Tiger tip the scales at 13½ pounds. This was Garcia's principal guitar for the next eleven years.
In 1990, Irwin completed Rosebud, Garcia's third custom guitar. It was similar to his previous guitar Tiger in many respects, but featured different inlays and electronics, tone and volume controls, and weight. Rosebud, unlike Tiger, was configured with three humbuckers; the neck and bridge pickups shared a tone control, while the middle had its own. Inside the guitar, a Roland GK-2 synthesizer was used in junction with GR-50 rack mount, producing the MIDI effects heard during live performances of this period. Sections of the guitar were hollowed out in order to bring the weight down to 11½ pounds. The inlay, a dancing skeleton holding a rose, covers a plate just below the bridge. The final cost of the instrument was $11,000.
In 1993, carpenter-turned-luthier Stephen Cripe tried his hand at making an instrument for Garcia. After researching Tiger through pictures and films, Cripe set out on what would soon become known as Lightning Bolt, again named for its inlay. The guitar used Brazilian rosewood for the fingerboard and East Indian rosewood for the body, which, with admitted irony from Cripe, was taken from a 19th century bed used by opium smokers. Built purely from guesswork, Lightning Bolt was a hit with Garcia, who began using the guitar exclusively. Soon after, Garcia requested that Cripe build a backup of the guitar. Cripe, who had not measured or photographed the original, was told simply to "wing it."
Cripe later delivered the backup, which was known by the name Top Hat. Garcia bought it from him for the price of $6,500, making it the first guitar that Cripe had ever sold. However, infatuated with Lightning Bolt, Garcia rarely used the backup.
After Garcia's death, the ownership of his Wolf and Tiger came into question. According to Garcia's will, his guitars were to go to Doug Irwin, who had constructed them. The remaining Grateful Dead members disagreed—they considered his guitars to be property of the band, leading to a lawsuit between the two parties. In 2001, Irwin won the case. However, due to being a victim of a hit-and-run accident in 1998, Irwin was left nearly penniless. This forced him to set Garcia's guitars up for auction in hopes of being able to start another guitar workshop.
On May 8, 2002, Wolf and Tiger, among other memorabilia, were placed for auction at Studio 54 in New York City. Tiger was purchased for $957,500, while Wolf was bought for $789,500. Together, the instruments were bought for 1.74 million dollars, setting a new world record. Tiger is in the private collection of Indianapolis Colts owner Jim Irsay.