- 1963 (26 years old) | 1963
By the end of 1963, Bobby met Sharon (Didi, Dee Dee) Morrill, which resulted in a marriage officiated by Bob Alexander (a member of the Beat Generation). The wedding took place at Zack Walsh’s house. The marriage was never legalized since the paperwork was never filed. Bobby and Didi relocate to Beverly Glenn.
- 1964 (27 years old) | 1964
Sometime in 1964, Bobby and Didi tried to smuggle drugs into New York City. According to Sharon’s brother, Terry Morrill, he states: “they were both (Bobby and Didi) doing many drugs. The three of us then decided to go to New York planning to sell a bunch of pot, then fly to Crete, but we got ripped off, and Bobby and Didi fled to Montreal”. After hiding in Canada, Didi returned to Los Angeles, and Bobby went to New York.
In 1964, before the drug smuggling occurred, Bobby worked as a carpenter for a construction company in Los Angeles.
Bobby’s parole from his 1961 arrest expired later that year.
- 1965 (28 years old) | 1965
In 1965, a year after his parole expired, he relocated to New York. People from the Beat Generation relocated here as well. Bobby became part of Andy Warhol’s Greenwich Village art community known as the Factory, where he still focused on his artistic talents, such as making collages and writing poetry.
In 1965, early in his tenure at the Factory, Driscoll gave his last known film performance, in experimental filmmaker Piero Heliczer’s underground movie Dirt, alongside Sharon Morrill.
- 1966 (29 years old) | 1966
In the winter of 1966, Bobby wrote the poem titled “The Sunday Bonnett.” for his girlfriend Didi Morrilll.
- 1967 (30 years old) | 1967
In 1967, while he was 30 years old, his other poems were published in an underground book, The Great Society. By the end of 1967, he broke up with Didi. His funds depleted, he disappeared into the underground in late 1967 or early 1968, completely dispirited and very ill from Hepatitis due to his substance abuse.