In Madrid, Spain, he became an accomplished blues player as he hitchhiked and supported himself by busking with his harmonica. While visiting Aberdeen, Scotland, with no money and nowhere to sleep, he claimed that the locals were very hospitable by offering him somewhere to stay. In later interviews, Lewis would reveal other encounters he had traveling around Europe. He talked about hanging out at the airport for three days until he stowed away on a plane to Europe. In an interview with David Letterman, Lewis talked about hitchhiking across the country back to New York City and how he learned to play the harmonica while waiting for rides. His mother was close friends with the Grateful Dead's manager and extended family.

Lewis credits Welch with inspiring him in his early teenage years. His mother had an extramarital affair with Beat Generation poet Lew Welch, who became his step father. Lewis attended Cornell University in Ithaca, New York. He was also an all-state baseball player. He attended and graduated from the Lawrenceville School, a then-all-male prep school in New Jersey, in 1967, and he achieved a perfect score of 800 on the math portion of the SAT.

Lewis was raised in Marin County, California, living in Tamalpais Valley and Strawberry, and attending Strawberry Point Elementary School (where he skipped second grade) and Edna Maguire Junior High School in Mill Valley.

His grandfather, Hugh Cregg, was district attorney of Essex County, Massachusetts from 1931 to 1959. His father, Hugh Anthony Cregg Jr., was an Irish-American from Boston, and his mother, Maria Magdalena Barcinska, was Polish, from Warsaw.

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