Carradine was born on December 8, 1936 as John Arthur Carradine, in Hollywood, California, the oldest child of actor John Carradine and his wife Ardanelle Abigail (McCool). He was a half-brother of Bruce, Keith, Christopher, and Robert Carradine, and an uncle of Ever Carradine and Martha Plimpton, most of whom are also actors. Primarily of Irish descent, he was a great-grandson of Methodist evangelical author Beverly Carradine and a grandnephew of artist Will Foster. Called Jack by his family, Carradine's childhood was turbulent.

By his own account, in the late 1950s, while living in San Francisco, Carradine was arrested for assaulting a police officer. He pled guilty to a lesser charge of disturbing the peace. While in the Army, he faced court-martial, on more than one occasion, for shoplifting. After he became an established actor and had changed his name to David, he was arrested in 1967 for possession of marijuana.  At the height of his popularity in Kung Fu, in 1974 Carradine was arrested again, this time for attempted burglary and malicious mischief. While under the influence of peyote, Carradine began wandering nude around his Laurel Canyon neighborhood. He broke into a neighbor's home, smashing a window and cutting his arm. He then bled all over the homeowner's piano. At some time during this incident he accosted two young women, allegedly assaulting one while asking if she was a witch. The police literally followed a trail of blood to his home. The burglary charges were dropped when nothing was found to be missing. Carradine pleaded no contest to the mischief charge and was given probation. He was never charged with assault, but the young woman sued him for $1.1 million and was awarded $20,000.  In 1980, while in South Africa filming Safari 3000 (also known as Rally), which co-starred Stockard Channing, Carradine was arrested for possession of marijuana. He was convicted and given a suspended sentence. He claimed that he was framed, in this case, by the apartheid government, as he had been seen dancing with Tina Turner.  During the 1980s, Carradine was arrested at least twice for driving under the influence of alcohol, once in 1984 and again in 1989. In the second case, Carradine pleaded no contest. Of this incident, the Los Angeles Times reported: "legal experts say Carradine was handed a harsher-than-average sentence, even for a second-time offender: three years' summary probation, 48 hours in jail, 100 hours of community service, 30 days' work picking up trash for the California Department of Transportation, attendance at a drunk driving awareness meeting and completion of an alcohol rehabilitation program."  In 1994, while in Toronto filming Kung Fu: The Legend Continues, Carradine was arrested for kicking in a door at SkyDome while attending a Rolling Stones concert. When asked his reasoning, Carradine claimed he was worried about getting swarmed by people who recognized him, and so entered the building as quickly as possible. Answer this question using a quote from the following article:

When was he first arrested?
in the late 1950s, while living in San Francisco, Carradine was arrested for assaulting a police officer.