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During his career, he released only two albums but charted 12 singles on the Billboard country charts, and 7 more after his death. He began his career there in , performing in Ralph Stanley 's band.

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Establishing himself as a lead singer in bluegrass music, Whitley moved to Nashville in and began his recording career there. Years of alcoholism severely compromised his health and he died of alcohol intoxication in at his Goodlettsville home at the age of While Whitley was a teenager in Sandy Hook, he and his friends would pass the time drinking bootleg bourbon and racing their cars down mountain roads at dangerous speeds.

The car wrecked, killing his friend and almost breaking Whitley's neck. In another incident, he drove his car off a foot 37 m cliff into a frozen river, escaping with only a broken collar bone. Whitley's older brother Randy was killed in an October motorcycle accident. Whitley is known for his neotraditional brand of country popularized by hit artists such as George Strait and Randy Travis.

In , he performed in a musical contest in Ezel, Kentucky , with brother Dwight on five-string banjo. Ricky Skaggs was also in the contest.

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Skaggs and Whitley instantly bonded and subsequently became close friends. Whitley and Skaggs, both sixteen years old, were discovered in Ft. Gay, West Virginia, by Ralph Stanley , who was 45 minutes late for a gig due to a flat tire. However, it was Whitley and Skaggs, who "sounded just like me and Carter in the early days". Whitley became lead singer for Stanley in His singing was heavily influenced by Carter Stanley and Lefty Frizzell.