Bob was born and raised in Orléans, Ontario. Bob’s early years were filled with the fiddle sounds of his father Rhéal and uncle Gérard. At age 14, he picked up his father’s 5 string banjo playing bluegrass music along with his brothers at family gatherings. A few years later, after hearing Merv Wilson play the pedal steel, Bob decided to purchase a pedal steel guitar of his own. He learned the rudiments of the pedal steel under the guidance of Claude "Quincy" Damphousse, Brian Ostrom and Al Bragg.
From 1979 to 1983, Bob was a proud member of Terry Carisse and Tracks travelling across Canada. Being his first professional road band, Bob had the opportunity to hone his skills with one of the best singer songwriters in the business. In the mid 80’s, Bob spent time in Manchester, England where he composed music for BBC TV with his brother Jean. The television contracts enabled Bob to use the pedal steel guitar in Country, Jazz, Blues, Folk, and Latin compositions.
Over the years, he worked on recording sessions and freelanced with various bands backing artists such as Anita Perras, Tim Taylor, Johnny Burke, Sneezy Waters, Joséphine, The BeBop Cowboys, The Royal Crowns and Thelonious Hank. In 1995, Bob released "Nouveau Steel", a recording that won the Durham Region best Jazz recording award. Bob’s brothers Jean and Michel contributed guitar solos and compositions to the project. A few years later, Bob produced "Northern Steel I" and "Northern Steel II" featuring top Canadian Steel players to critical acclaim. In 2005, Bob released "Bob Taillefer y Los Hermanos", a recording that also won the Durham Region best Jazz recording. The project featured compositions by his brother Michel. These recordings led to an opportunity to represent Canada at Scotty’s International Steel Guitar Convention in St Louis and other Steel Guitar Shows in the United States, Ireland and England.
In 2008, The Pedal Steel Guitar Association of Floral Park New York presented Bob with the Clay Savage Memorial Appreciation Award for outstanding contribution to the art of playing the steel guitar and furthering knowledge to players of the instrument.