Born Sept. 10, 1937, in Oklahoma City, the singer came by his talent naturally. His cousin Gene Austin (who he called his uncle) was a prominent entertainer starting in the 1920s. Overstreet recalled in a 2014 interview with Billboard, while promoting his book A Road Less Traveled, some important advice Austin gave him.
"My uncle told me that you had to sing from the heart and you had to have songs that touched and spoke to other people's hearts. That's what I tried to do with all of my songs. I tried to think about who I was singing to, and I wanted to touch their hearts."
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Overstreet decided he wanted to try his hand at a similar career and began performing on Slim Willet's television series in Abilene, Texas, when he was 17. Soon thereafter, he formed a band called the Shadows.
Overstreet recorded at Norman Petty's studio in Clovis, N.M., as well as a New York session that included future Tonight Show band member Doc Severinsen on trumpet. Still, success as a recording artist eluded the singer. He moved to Nashville in 1967 to manage the Music City operations at Dot Records. Though he enjoyed his work, the singer never gave up his dreams of the stage, electing to become a recording artist for the label.
He first charted with 1969's "Rocking a Memory (That Won't Go to Sleep)," which peaked at No. 73 on the Billboard Hot Country Songs chart. It wouldn't take long for him to eclipse that peak, with 1971's "Gwen (Congratulations)" making it all the way to No. 5. That would be the first of 23 appearances in the top 40. His biggest hit was 1972's "Ann (Don't Go Runnin)," which narrowly missed the top of the chart, settling in at No. 2.
Overstreet's rich voice, combined with his muscular build and movie-star looks, helped propel him into the spotlight as a frequent guest on the top TV variety shows of the day, such as Hee Haw and The Midnight Special. His final appearance on the charts came in 1986 with "Next to You," which made it to No. 74.
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In the late 1980s, the singer became one of the first country performers to base his operations in Branson, Mo., which became a haven for artists who still had devoted fanbases. He said it was love from the start.
"I had a friend who had moved there, and he said, 'Tommy, you've got to come see this place.' He had become a little disenchanted with Nashville. I fell in love with the area, and we lived there for about seven years."
It was a slower pace for the singer, who admitted that his fast pace of the 1970s might have cost him. "There were 329 one-nighters, then 36 days in Nashville in a year's time," he said. "I also recorded two albums and did a European tour for 18 days. Unfortunately, my ex-wife and I separated and divorced. The music business and what we do in that career is not great for relationships. You're gone too much. I wouldn't encourage anyone to work that hard. I shouldn't have. I should have stopped and smelled the roses and spent more time with my family. But you learn those things in hindsight. Hindsight is 20/20. As you go down this road, you do what you think is the best thing at the time, and I did. Unfortunately, it cost me some heartbreak and disappointments, but that's how life is."
Things ended on a happy note for the singer, who remarried and had two more children. "Life is dear to me," he said. "I've had a wonderful time, met some interesting people, and had some success along the way. I've had a blessed life, and I can't complain at all."
Arrangements for Overstreet's memorial servies are pending.