- Wold left home at 13 to avoid abuse at the hands of his stepfather, and lived rough and on the road in Tennessee, Mississippi and elsewhere, until 1973. He would travel long distances by hopping freight trains, looking for work as a farm laborer or in other seasonal jobs, often living as a hobo.
- Although he had been playing music for decades, he did not have his first major chart-topping success until he was sixty-five years old.
- He has played with Janis Joplin, Joni Mitchell, John Paul Jones, Jack White, Dave Grohl, Nick Cave,.
- His tours in October 2008 and January 2009 were all sold out and included performances at the Royal Albert Hall, the Edinburgh Queen's Hall, the Grand Opera House in Belfast, the Apollo in Manchester, the City Hall in Newcastle and the London Hammersmith Apollo.
- He has played at the V Festival, Glastonbury, and the North Sea Jazz festival.
- Experienced his first major success when he appeared on Jools Holland annual Hootenanny in 2006.
- Released his first album with ''The Level Devils'' at the age of sixty and his first solo album at sixty-three.
- Has been homeless multiple times throughout his life.
- Produced several albums for Modest Mouse in the nineties.
- Worked as a carnival worker, cowboy and migrant worker at various times.
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