As Cline's career took off in the late 1950's, Jim stayed around Winchester and kept his day job at Montgomery Wards. Finally, he had to make a choice when he was asked to become the morning disc jockey at WHPL, a new station that debuted in Winchester in December 1960. "I wasn't really sure I wanted to do that because I had a pretty good job there at Wards, making $40 a week," he says. But he decided to make the leap into a fulltime radio and musical career. Things moved fast for the next few years for Joltin' Jim.

In 1961, Jim's first record was released on Nashville Records, a subsidiary of Starday-King, a major country label. The record, called "That's What Makes The World Go Around," was produced by Tommy Hill, a country music pro who had written several hits. It made a small splash. During his trips to Nashville, Jim visited Patsy Cline and her husband Charlie Dick, and he became closer to Ernest Tubb. He was invited to Tubb's home and hung out with him and some of the other Music City personalities of the time, including Ray Price, Willie Nelson, and songwriter Harlan Howard.

A couple of years later, Jim looked like he was about to break into the top ranks himself. His new one, "Which A Way, What A Way, Any Way," was a pick hit by Billboard, Record World, and Cash Box, which predicted, "A catchy new song, watch it go." The record, a humorous Larry Kingston-penned song about a missing wife, sounds fresh even today. "But it didn't go," Jim says sadly. "You know the business. It's very rough to make it." About the same time, the master tapes for his first LP were lost when the record-pressing company went bankrupt. Jim is not one to dwell on his disappointments, however, saying only, "There's been heartaches from this business."

Wisely, McCoy kept joltin' around and didn't put all of his eggs in the Nashville basket. He continued to perform locally and made frequent appearances across the Eastern Panhandle. Some of these performances included Jack Waugh's place in Berkeley Springs; the Old Orchard Inn (now Rainbow Road) in Rippon; Moose, Eagles, and VFW halls in Martinsburg; and even the famous Berkeley Castle in Berkeley Springs. Meanwhile, he stayed on the air at WHPL and promoted concerts featuring some of the newer country music acts. He also started a music publishing firm, publishing his own songs and tunes by other writers.

About this time, he teamed up with Jean Alford, a Virginia singer-songwriter, and launched Alear Records. The third Alear release, "It's a Big Old Heartache" by Teenie Chenault of Richmond, looked like it would be the big payoff for their efforts. As the song gathered airplay, record distributors began calling, and they rushed to ship out more copies. Unfortunately, they were never paid for most of those records, Jim says.

McCoy and Alford recorded some of their product in Nashville, such as Al Hogan's version of "He Didn't Become Famous For His Song," a telling title if ever there was one. The records often featured tunes written by McCoy or Alford and were usually pressed by Rite Records or Queen City in Cincinnati.

By the late 1960's, the McCoy-Alford partnership became strained, and Jim started his own Winchester Records, complete with a label picturing a big apple to symbolize the Virginia city. A string of regional performers trooped through his studio at 314 Lanny Drive. Aside from recordings by Jim McCoy and Jean Alford themselves, the Alear and Winchester catalogues included material by country singers Mel McQuain and Frank Darlington, both of Martinsburg; gospel music performer Kenny Johnson of Hedgesville; and the fairly well-known Carroll County Ramblers from nearby Maryland. The majority of the singers they recorded were country artists, but there were also releases by The Lone Star - a folk-rock singer from Romney whose real name was John Mark Hott - and by The Smacks - a Winchester rock group. Most of the records were 45 rpm, but there were also a few album releases. The records were often well-received and won attention in their home areas.

McCoy generally produced and engineered the recordings himself, and even when a singer was less than inspiring, the sound quality of Winchester's output was surprisingly good. He mixed the sound while listening to small speakers, rather than big studio ones, so that he could hear what people would hear at home. Jim always sought what he calls a "bitey sound" for the guitar, a lively sound that could be heard on his own records. Jim says that he tried to keep a copy of everything he released, but just couldn't seem to hold on to them. Sometimes, a group would even walk out the door with the master recording.