His father played boogie-woogie piano and Wold tried to learn when he was five or six, but could not. At the age of eight, he learned to play the guitar from K. C. Douglas, who worked at his grandfather's garage, later realizing that he had been taught the blues.
Douglas wrote the song "Mercury Blues" and had played with Tommy Johnson in the early 1940s. 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 labourer or in other seasonal jobs, often living as a hobo. At various times, Wold worked as a carnie, a cowboy and a migrant worker.
Paraphrasing H. L. Mencken, Wold described this time of his life by saying "Hobos are people who move around looking for work, tramps are people who move around but don't look for work, and bums are people who don't move and don't work. I've been all three." When asked about his nickname, Wold has said: "because it's just true: I always get seasick".
When he was ill on a ferry from Norway to Copenhagen, later in his life, a friend began playfully using the name and, despite Wold not rising to it for a while, it stuck. When asked about his name on British Sunday morning television show, Something for the Weekend, he replied, "I just get sick on boats". On Top Gear, when asked about his name, Wold replied "Well, I guess I just don't like boats!" Wold made his first UK television appearance on Jools Holland's annual Hootenanny BBC TV show on New Year's Eve 2006. He performed a live rendition of "Dog House Boogie" on the "Three String Trance Wonder" and the "Mississippi Drum Machine".
After that show his popularity exploded in Britain, as he explained in an interview: "I can't believe it, all of the sudden I'm like the cat's meow!" He was well received in the UK, winning the 2007 MOJO Award for Best Breakthrough Act and going on to appear at major UK festivals such as Reading, Leeds and Glastonbury. In 2007 he played more UK festivals than any other artist. Wold toured early in 2008, playing in various venues and festivals in the UK. He was joined on stage by drummer Dan Magnusson. KT Tunstall also dueted with Wold at the London Astoria in January 2008. Wold also played many other festivals throughout the world in 2008, including Fuji Rock in Japan, East Coast Blues & Roots Music Festival in Australia, also in April 2008, and Roskilde in Denmark. Wold's major-label debut, I Started Out with Nothin and I Still Got Most of It Left was recorded with Dan Magnusson on drums, was released by Warner Music on September 29, 2008, and features Ruby Turner and Nick Cave's Grinderman. He has toured the UK extensively since 2007 being supported by Duke Garwood, Gemma Ray, The Sugars, Billie the Vision and the Dancers in January 2008, Amy LaVere in October 2008, Melody Nelson at the Brighton Dome on 7 October, and Joe Gideon & The Shark in January 2009.
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. In 2009, Wold was nominated for a Brit Award in the category of International Solo Male Artist, That same year, BBC Four broadcast a documentary of Wold visiting the southern USA entitled Seasick Steve: Bringing It All Back Home. On January 21, Wold hosted "Folk America: Hollerers, Stompers and Old Time Ramblers" at the Barbican in London, a show that was also televised and shown with the documentary on BBC Four as part of a series tracing American roots music. In an interview with an Australian magazine, Wold attributes much of his unlikely success to his cheap and weather-beaten guitar, "The Trance Wonder" and reveals the guitar's mojo might come from supernatural sources. "I got it from Sherman, who is a friend of mine down in Mississippi, who had bought it down at a Goodwill store. When we were down there last time he says to me, 'I didn't tell you when you bought it off me, but that guitar used to be haunted'. I say, 'What are you talking about, Sherman?'.
He says, 'There’s 50 solid citizens here in Como who'll tell you this guitar is haunted. It's the darnedest thing – we’d leave it over in the potato barn and we'd come back in and it would be moved. You'd put it down somewhere and the next morning you’d come back and it would have moved. When you took that guitar the ghost in the barn left'.
He told me this not very long ago and I said to him, 'Sherman! Why didn't you tell me this before?' and he said, 'Well the ghost was gone – I didn't want it around here no more!'" On January 3, 2010, Wold appeared on the popular BBC motoring show Top Gear as the Star In A Reasonably Priced Car. He was the last star to drive in the blue Chevrolet Lacetti. In February 2010, Wold was nominated for a Brit Award in the category of International Solo Male Artist for the second consecutive year. In 2010, Wold made numerous festival appearances throughout the summer, including the Pyramid Stage at the Glastonbury Festival, the main stage at V Festival, the main stage at the Hop Farm Festival and many more. In February 2011, Wold signed to Play It Again Sam to release his new album with the exception of the US, where it will be released on Third Man Records. Subsequently his new album You Can't Teach an Old Dog New Tricks was released on his new labels and it was announced that former Led Zeppelin bassist John Paul Jones had played on the new album, and performed alongside Wold to promote it. This caused some to believe that he will tour with Wold as a part of his backing band, joining his then-current drummer Dan. John Paul Jones did indeed appear onstage to play with Wold at the Isle of Wight 2011 festival and on the main stage of Rock Werchter 2011. On 16 August 2014 he was the headline act at Beautiful Days in Exeter, UK, and on the 24th August he headlined at 'Victorious Festival' in Southsea, Portsmouth, UK.
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