In addition to his solo material, Dudek has played guitar with Steve Miller Band, The Dudek-Finnigan-Krueger Band, Stevie Nicks, Cher, Boz Scaggs, The Allman Brothers Band, as well as Maria Muldaur, Bobby Whitlock, Mike Finnigan, Jim Krueger and Dave Mason.
Dudek's father, Harold, was born in Campbell, Nebraska, and was a World War II veteran in the United States Navy. His mother, Alma, born in Brooklyn, was a former Radio City Music Hall Rockette. Les has one older sister, Sandy, who was born in Brooklyn. The family is of Czech, German, Italian, and Russian descent. Six years after Les was born, his father retired from the Navy and the family moved to Florida where he grew up.
The Beatles caught Dudek's ear at an early age. In 1962, at the age of ten, Les asked his parents for a guitar for Christmas. They bought him an acoustic guitar from Sears & Roebuck. His musical influences, along with The Beatles, were Cream, Jimi Hendrix, and The Ventures. He had built quite a reputation around the Florida area as a proficient guitar player, having started playing in local bands as a teenager. Those bands were "The United Sounds", "Blue Truth" and "Power". That reputation would place him in the studio with the Allman Brothers Band for the recording of the Brothers & Sisters album. He played guitar harmonies with Dickey Betts on the well-known song "Ramblin' Man" and acoustic guitar on "Jessica". In Alan Paul's book, One Way Out: The Inside History of the Allman Brothers Band, Dudek claimed to have written the part in "Jessica" from when it modulated into G then eventually back to A.

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