In the mid-1960s, Tillis switched to Kapp Records, and in 1965, he had his first Top 15 hit with "Wine". Other hits continued to follow, such as "Stateside" and "Life Turned Her That Way", which was later covered by Ricky Van Shelton in 1988, going to No. 1.
He wrote for Charley Pride ("The Snakes Crawl At Night") and wrote a big hit for Kenny Rogers and The First Edition called "Ruby, Don't Take Your Love to Town". He also wrote the hit "Mental Revenge" for Outlaw superstar Waylon Jennings. (It has also been covered by the Hacienda Brothers, Linda Ronstadt, Gram Parsons, Barbara Mandrell, and Jamey Johnson.) In 1968, Tillis achieved his first Top 10 hit with "Who's Julie". He also was a regular featured singer on The Porter Wagoner Show.
The height of his career
Things turned around in 1969 for Tillis. He finally achieved the success he always wanted with two Top 10 country hits, "These Lonely Hands of Mine" and "She'll Be Hanging Around Somewhere". In 1970, he reached the Top 5 with "Heart Over Mind", which peaked at No. 3 on the Hot Country Songs list.
After this, Tillis' career as a country singer went into full swing. Hits soon came quite easily, such as "Heaven Everyday" (1970), "Commercial Affection" (1970), "Arms of a Fool" (1970), "Take My Hand" (a duet with Sherry Bryce in 1971), and "Brand New Mister Me" (1971). In 1972, Tillis achieved his first chart-topper with his version of his song "I Ain't Never". Even though the song was previously a hit by Webb Pierce, Tillis' version is the better-known version of the two. Most of the above-mentioned song hits were recorded on MGM Records, Tillis' record company in the early part of the decade. He also appeared on Hee Haw singing ' I Talked About You All Over Town' and 'Living and Learning' with Sherry Bryce.
After the success of "I Ain't Never", Tillis had another hit, which came close to No. 1 (reaching No. 3), titled "Neon Rose", followed by "Sawmill", which reached No. 2. "Midnight, Me and the Blues" was another near chart-topper in 1974.
Other hits Tillis had on MGM include "Stomp Them Grapes" (1974), "Memory Maker" (1974), "Woman in the Back of My Mind" (1975), and his version of "Mental Revenge" (1976). Tillis achieved his biggest success with MCA Records, with which he signed in 1976. It started with a pair of two No. 1 hits in 1976, "Good Woman Blues" and "Heart Healer". (In an interview, he mentioned having written five hits in one week.)
Thanks to this success, in 1976 Tillis won the Country Music Association Awards' most coveted award, Entertainer of the Year, and was also inducted into the Nashville Songwriters Hall of Fame that year. He achieved another No. 1 in 1978 with "I Believe In You" and then again in 1979 with "Coca-Cola Cowboy", which was put in the Clint Eastwood movie Every Which Way but Loose, in which he also made a cameo appearance.