Sonny began playing banjo at age 11, when he was in the sixth grade.  His brother, Bobby, was working in West Virginia with the Lonesome Pine Fiddlers at that time.  Larry Richardson was playing banjo with Bobby and sometimes he would come home with Bobby.  When Sonny saw and heard Larry play, he felt that he could learn to do that, and asked Larry to show him how to play.  However, Larry would play his banjo with his back to him so Sonny couldn't see his fingers.  Sonny vowed to learn how to play on his own, and he soon did just that.  He began by convincing his dad to buy him a $100 Kay five string banjo and they ordered it through the school music department.  Before the banjo arrived, Sonny remembers sitting in class at school, trying to figure out a Ralph Stanley break on "We'll Be Sweethearts in Heaven".   Sonny felt he had the right hand figured out for that song, and also "Cripple Creek".  A few weeks later when the banjo finally arrived, to the amazement of his Dad, music teacher and himself, Sonny was immediately able to play it.  He practiced at least five, and sometimes as much as 15 hours a day, out on the back porch swing.  Often he'd still be up at 4:45 a.m., at which time he would hurry off to bed and pretend to be asleep before his father awoke for work at 5:00 a.m. and checked on him.  Sonny says his father never was the wiser.  

Shortly thereafter, Sonny began playing music with some local musicians, Claude Stewart, Jerry Williams, and Carl Eldridge.  He also went on a trip with his family to West Virginia to see Bobby.  At that time, the Lonesome Pine Fiddlers band consisted of Bobby, Jimmy Martin, Ezra Cline, Charles Cline, and "Little Robert" (A. Vanwinkle). Sonny was allowed to stay a few weeks in West Virginia and play with them.  It was during this time period that Bobby and Jimmy Martin made the recordings for King.  Sonny was in the studio with them but did not play.  

Sonny played Junior High basketball and baseball, and in the 9th grade he made the Varsity football team.  Sonny states that he was "too lazy to play", even though he was approached by some colleges about going to school and playing football.  Bobby was in Korea at this time, in the United States Marine Corp.  When school was out in June of 1952,  Jimmy Martin and Sonny went to Beanblossom, Indiana to see Bill Monroe.    Bill hired Jimmy, and with Jimmy's insistance, also hired 14 year old Sonny. A week later they were off to Nashville.  On Sonny's first Grand Ole Opry appearance with the Bluegrass Boys, he performed "Rawhide".  It was during this time period when Sonny recorded nine tunes with Monroe. This was quite an experience for 14 year old Sonny, and he continued as a Bluegrass Boy through the summer until school started in September.    

Sonny describes his 10th grade year as a "disaster".  His parents had moved from the farm and the relatively small Jefferson Township High School to Dayton, Ohio and the very large Fairview High School.  Once again, the powers that be wanted him to play football and Sonny refused.  School was rather difficult, from that point.   However, it was around this time that Sonny met his wife, Judy, of over 40 years, who happened to live across the street from the Osborne family.   That following April, Bill Monroe came through Dayton.  Sonny persuaded his father to allow him to go with Bill to Toledo, Ohio and "play a date or two" with him.  By now, Sonny knew this was what he wanted to do with his life.  When they returned, Bill asked Sonny's father if he could go to work with him on a permanent basis.  Sonny's father agreed on the condition that Bill would "look out for him".    Sonny said that was the last he ever heard of that conversation, and at age 15, he found himself naive and out on his own, with Jimmy Martin, Charlie Cline and Bill Monroe to learn from.  Sonny stayed with Bill until Bobby's release from the Marine Corp.  

Sonny & Bobby began their career performing together on November 6, 1953, at WROL Radio in Knoxville, Tennessee.