Having previously studied at the San Francisco Art Institute as a teenager, Garcia embarked on a second career in the visual arts in the late 1980s. He created a number of drawings, etchings, and water colors. Garcia's artistic endeavors were represented by the Weir Gallery in Berkeley, California from 1989 to 1996. During this period, Roberta Weir (unrelated to Garcia's bandmate Bob Weir) provided Garcia with new art techniques to use, sponsored his first solo show in 1990, and prepared blank etching plates for him to draw on. These would then be processed and printed by gallery staff and brought back to Garcia for approval and signature, usually with a passing of stacks of paper backstage at a Dead show. His annual shows at the Weir Gallery garnered much attention, leading to further shows in New York and other cities. Garcia was an early adopter of digital art media; his artistic style was as varied as his musical output, and he carried small notebooks for pen and ink sketches wherever he toured. Roberta Weir continues to maintain an archive of the artwork of Jerry Garcia. Perhaps the most widely seen pieces of Jerry Garcia's art are the many editions of men's neckties produced by Stonehenge Ltd. and Mulberry Neckware. Some began as etchings, other designs came from his drawings, paintings, and digital art. Garcia's artwork has since expanded into everything from hotel rooms, wet suits, men's sport shirts, a women's wear line, boxer shorts, hair accessories, cummerbunds, silk scarves and wool rugs.
During the autumn of 1978, Garcia developed a friendship with Shimer College student Manasha Matheson, an artist and music enthusiast. They remained friends over the following nine years before initiating a romantic relationship in Hartford, Connecticut on the Grateful Dead's spring 1987 tour. On August 17, 1990, Jerry and Manasha married at their San Anselmo, California home in a spiritual ceremony free of legal convention. Jerry and Manasha became parents with the birth of their daughter, Keelin Noel Garcia, on December 20, 1987. In 1991, Garcia expressed his delight in finding the time to "actually be a father" to Keelin in contrast to his past relationships with his children. A year later, Garcia dedicated his first art book, Paintings, Drawings and Sketches, "For Manasha, with love, Jerry."
Amid a litany of personal problems, Mydland died of a speedball overdose in July 1990. His death greatly affected Garcia, leading him to believe that the band's chemistry would never be the same. Before beginning the fall tour, the band acquired keyboardists Vince Welnick and Bruce Hornsby. The power of Hornsby's performances drove Garcia to new heights on stage. However, as the band continued through 1991, Garcia became concerned with the band's future. He was exhausted from five straight years of touring. He thought a break was necessary, mainly so that the band could come back with fresh material. The idea was put off by the pressures of management, and the touring continued. Garcia's decrease in both stamina and interest to continue touring caused him to use heroin again after several years of intermittent prescription opiate use. Though his relapse was brief, the band was quick to react. Soon after the last show of the tour in Denver, Garcia was confronted by the band with another intervention. After a disastrous meeting, Garcia invited Phil Lesh over to his home in San Rafael, California, where he explained that after the meeting he would start attending a methadone clinic. Garcia said that he wanted to clean up in his own way, and return to making music.
In 1990, Irwin completed Rosebud, Garcia's fourth 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. Atop the guitar was a Roland GK-2 pickup which fed the controller set inside the guitar. The GK2 was used in junction with the Roland GR-50 rack mount synthesizer. The GR-50 synthesizer in turn drove a Korg M1R synthesizer producing the MIDI effects heard during live performances of this period as heard on the Grateful Dead recording Without a Net. Sections of the guitar were hollowed out to bring the weight down to 11 ⁄2 pounds (5.2 kg). The inlay, a dancing skeleton holding a rose, covers a plate just below the bridge. The final cost of the instrument was $11,000 (equivalent to $21,500 in 2019).