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On This Day in Country Music: October 14

Your daily look at this day in country history, from classic Opry nights to the newest No. 1 hits.

What happened on October 14 in country music history?

On October 14, 1985, George Strait won Male Vocalist and Album of the Year for Does Fort Worth Ever Cross Your Mind at the CMA Awards. In 1974, Johnny Cash hosted the eighth CMA Awards at the new Grand Ole Opry House. Melba Montgomery and Natalie Maines share this birthday.

THE BIG MOMENT1985

George Strait won Male Vocalist and Album of the Year for Does Fort Worth Ever Cross Your Mind at the CMA Awards

George Strait won Male Vocalist and Album of the Year for Does Fort Worth Ever Cross Your Mind at the CMA Awards. Reba McEntire was Female Vocalist, The Judds won Vocal Group, and Lee Greenwood's "God Bless the USA" was Song of the Year. Ricky Skaggs was Entertainer of the Year.

Country Stars Born on October 14

1938

Melba Montgomery

Melba Montgomery was born in Iron City, Tennessee. She sang a string of 1960s duets with George Jones and topped the country chart in 1974 with "No Charge." She also wrote songs for George Strait and Terri Clark. She died in Nashville in January 2025 at 86.

Read our story ›

1974

Natalie Maines

Natalie Maines was born in Lubbock, Texas. As lead singer of The Chicks, then called the Dixie Chicks, she sang on six No. 1 country hits, including "Wide Open Spaces," "Cowboy Take Me Away" and "Travelin' Soldier."

No. 1 Songs on This Date

1957

The Everly Brothers reached No. 1 on the country chart with "Wake Up Little Susie." Written by husband and wife Felice and Boudleaux Bryant, the song also topped the pop chart.

1969

Johnny Cash at San Quentin was No. 1 on the country album chart, part of a 20-week run on top. Cash recorded it live for the prison's inmates. Its hit "A Boy Named Sue" later earned him a Grammy.

2017

Thomas Rhett's Life Changes was No. 1 on the country album chart for a third week. The album, which also topped the all-genre Billboard 200, included the No. 1 duet "Craving You" with Maren Morris.

Big Awards Nights

1970

Merle Haggard was the big winner at the fourth CMA Awards at the Ryman Auditorium. He took Entertainer and Male Vocalist, and "Okie From Muskogee" won both Album and Single of the Year. Tammy Wynette was Female Vocalist, and Kris Kristofferson won Song of the Year for "Sunday Morning Coming Down."

1974

Johnny Cash hosted the eighth CMA Awards at the new Grand Ole Opry House. Charlie Rich was Entertainer of the Year and won Album of the Year for Very Special Love Songs. Ronnie Milsap and Olivia Newton-John won the vocalist awards, and "Country Bumpkin" won Song and Single of the Year.

2020

Luke Combs was named Top Country Artist at the Billboard Music Awards, and his What You See Is What You Get won Top Country Album. Maren Morris, Dan + Shay and George Strait also won. Garth Brooks became the first country star to receive the ICON Award.

Source: musicrow.com

New Music on This Date

1996

Alan Jackson released "Little Bitty," a Tom T. Hall song about enjoying the simple things. The lead single from Everything I Love went on to become his 14th No. 1 country hit.

Love, Family and Life Events

2021

Zach Bryan shared that he had been honorably discharged from the U.S. Navy after eight years of service so he could make music full time. The news came just before his first headlining run, the Ain't For Tamin' Tour.

Source: whiskeyriff.com

Remembering the Ones We Lost

2006

Freddy Fender died at his home in Corpus Christi, Texas, at 69. The Tejano singer's "Before the Next Teardrop Falls" topped both the country and pop charts in 1975. He later played with the Texas Tornados.

More on Freddy Fender ›

Quick Answers

Which country singers were born on October 14?

Melba Montgomery (1938) and Natalie Maines (1974) were all born on this date.

What was the No. 1 country song on this date?

It depends on the year. In 1957, The Everly Brothers reached No. 1 on the country chart with "Wake Up Little Susie." In 1969, Johnny Cash at San Quentin was No. 1 on the country album chart, part of a 20-week run on top.

This Week in Country Music History

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Every entry is checked by the Country Thang Daily editors. Spot something we got wrong? Let us know and we’ll fix it and note the change.