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In November 1987, Sly was scheduled for two nights at the Las Palmas Theatre in L.A., where a Los Angeles Times reviewer found the sound system inadequate and Sly's voice "thin and strained when he tries to sing high melodies," perhaps a side effect of coke or uppers. Returning to the venue on the following night, Sly was arrested for allegedly owing $2,500 in back child support. The previous night's performance would count at his last real gig for almost twenty years.

Sly paid off his child-support debt the following month, but at some point prior to his scheduled preliminary hearing on drug charges in February 1988, he seems to have gone missing. It wasn't until November 14, 1989, that the watchful staff of the Los Angeles Times was able to report that Sly was being "held without bond in Connecticut pending extradition to California, where he is wanted on a 1987 drug-possession charge." The FBI informed the paper that "Stone has been living in Connecticut and New Jersey and has used the alias Sylvester Allen." Sly was returned to his home state and ordered to spend nine to fourteen months in a drug rehab center. Serena-Marie Sanfilipo, who'd tried to intervene in Florida years earlier, relocated to California to tend to Sly again. She took to parking outside his designated treatment center, to keep an eye on her charge. "He would mop the floor if someone else wouldn't mop it, so that people would like him," observes Serena. "He was an absolute perfect person in rehab. He did everything to make people happy [and] make people laugh. He played his keyboard. He was very joyful for other people, but he was just very lonely and sad.... He said, `As much as I hate being here, it's better than being in jail."' When she managed to get inside the center, "I would light a candle for him and we'd say a couple prayers and sing a couple songs, and he'd write music." After being discharged, "He was like a fawn," she remembers, "very fragile, having a tough time, but very happy." She says Sly then "cut ties with a lot of people that were negative," and that he invited her to move in with him. But she was put off by the threat of the return of bad habits. If Sly were ever turn over a new leaf, he would be the only one who could make himself stay away from the blow.

Sly grew ever more inaccessible to his biological family, including parents, siblings, and his three children. (Another daughter, Novena, had been born in the late '70s to Olenka Wallach of Sausalito, California.) "My brother's angry," Freddie told Spin in 1985, after withdrawing from his own cocaine habit. "He's been conned so many times, he's become a real con man himself." "I've cried into my pillow so many nights," added their mother, Alpha Stewart, "but I pray there's a God who can save Sly." Sly, in the same article, was dismissive of his connection with his own three offspring. "They do what they want," he stated. "I see them in and out."

Child-support bills, legal costs, and an estimated $3.4 million in back taxes, along with the disappearance of opportunities to record and perform, forced Sly to look for money. In September 1984, he sold his publishing interests to Mijac Music, owned by Michael Jackson, who was then on top of the music world (and a Sly admirer). Sly did manage to record several demos in the latter part of the '80s, some with fellow felon Billy Preston, but they weren't developed into moneymakers. For the 1987 movie Soul Man, Sly sang "Eek-A-Bo-Static" and a duet with Martha Davis of the Motels, "Love and Affection"; but neither charted.

Nostalgia-bound fans of the sounds of the Family Stone in the '60s and '70s might be tempted to assume that Sly's music would have faded in the '80s, even if its maker hadn't, due to changes in taste. Although the under-appreciation accorded Sly's post-bandbreakup recordings of the '70s may have been due in part their being out of step with the dominant disco sound, it's likely that Sly, who was always ahead of his time, could have stayed on the charts if his mental and financial resources hadn't been detoured