His signature song was "Six Days on the Road", and he is also remembered for "Vietnam Blues", "Truck Drivin' Son-of-a-Gun", and "Me and ol' C.B.".

Born in Spencer, Wisconsin, United States,[1] Dudley's grandparents came from Königsberg in East Prussia, Germany.

[4] In the original version of the song as recorded by Dudley the lyrics include the words "...I'm taking little white pills and my eyes are open wide..." a reference to the stimulants some truckers used to keep driving (and make their delivery times) when they needed sleep.

[2] Dudley scored more big hits in the 1960s, including "Truck Drivin' Son-of-a-Gun", "Trucker's Prayer" and "Anything Leaving Town Today".

[1] "Six Days on the Road" was subsequently recorded by several other artists including George Thorogood and the Destroyers, Steve Earle, The Flying Burrito Brothers and Sawyer Brown.

By the late 1970s, his success on the charts was beginning to fade, although Dudley amassed thirty-three Top 40 Country hits.

Dudley died on December 22, 2003, aged 75, after suffering a heart attack in his car in a parking lot in Danbury, Wisconsin.