Where does the loveable-outlaw image of the professional trucker first come into play in a big way in American culture? Perhaps the earliest notable instance came with Dave Dudley’s hit, “Six Days on the Road.” American culture expert Todd Uhlman makes that association in this ongoing "Overdrive’s Songs of the Highway" series, part of Overdrive's ongoing 60th anniversary celebration with coverage of trucking history: http://overdriveonline.com/trucking-history

“Six Days” remains in contemporary times one of trucking’s most popular songs -- a decade ago around Overdrive's 50th anniversary, readers voted the track as the No. 1 trucking song of all time: https://www.overdriveonline.com/channel-19/article/14875984/results-the-top-10-trucking-songs-of-all-time

It was initially record by Paul Davis and released in 1961, but it was Dudley who put it on the map with his version in 1963. It reached number two on the Billboard Hot Country Songs chart and crossed over at No. 32 on its broader Hot 100 chart.

A former trucker, Dudley packed the lyrics with details from the road. The song included references to speeding, popping pills, a “Georgia overdrive,” emitting black exhaust, dodging scales and being behind on his logs. ...