For 30 years, Country Music’s Biggest Night was hosted at the Grand Ole Opry House from 1974 to 2004. Ahead of this year's CMA Awards, we’re looking back at some of the show’s biggest moments to take place on the Opry House stage.

By Katie Quine ● November 8, 2018

1977 | Ronnie Milsap live Opry House album honored

Photograph courtesy of the Country Music Association

The consummate stage performer and master pianist, Ronnie Milsap recorded his first live album, Ronnie Milsap Live, at the Grand Ole Opry House in 1976, the same year that he became an Opry member.

A year later at the 11th annual CMA Awards, he’d find himself standing on the very same stage accepting three honors fueled by the success of the album. Album of the Year, Male Vocalist of the Year, and Entertainer of the Year all went to the singer.

1978 | Dolly Parton laughs through wardrobe mishap after top win

Photograph courtesy of the Country Music Association

Six years after Loretta Lynn became the first woman to win the CMA award for Entertainer of the Year, Dolly Parton became the second in 1978. Her acceptance speech stands out as one of the most memorable in all 52 years the award ceremony has been held. The sound of her name being called was accompanied by the mortifying rip of her dress. Kenny Roger’s then-wife Marianne offered her stole to Parton.

“I had this dress made in case I won. And about five minutes ago I was hoping I wouldn't win because I busted the front of it,” Parton endearingly joked to the crowd in the way only Dolly can. “My daddy said that's what I got for putting 50 pounds of mud in a five-pound bag."

1986 | Reba wins Entertainer of the Year after record-breaking year

Reba McEntire on stage the night she was inducted as an Opry member in January 17, 1986. She’d win big at the CMA Awards later in the year.

1986 was a good year for Reba McEntire. In January, she became a member of the Grand Ole Opry. The next month, Whoever’s in New England was her first album of twelve to reach No. 1 on Billboard’s Top Country Albums chart.

The success of the album’s title track and standout single “Little Rock” set the stage for an unforgettable 20th annual CMA Awards. Not only did McEntire snag her third consecutive Female Vocalist of the Year win (she’d win again in 1987), she took home the biggest award of the night: Entertainer of the Year.

In her acceptance speech, she recalled the time she was told that female country artists struggle to be successful. “Well, y’all just proved ’em wrong,” McEntire told the crowd. In 2018, she still holds the record as the most nominated woman in CMA Awards history.

1989 | Hank Williams honored for song 36 years after his death

Photograph courtesy of the Country Music Association

When Hank Williams Sr. recorded “There’s a Tear in My Beer” in 1950, country music was still 17 years away from having its first CMA Awards. Williams never officially released the song, but in 1988 his son did.

While Hank Williams Sr. died an untimely death in 1953, Hank Williams Jr. turned the song into a duet, building off the original recording. The song won Best Video and Vocal Event of the Year in 1989 and the father-son duo shared the honors as Hank Williams Sr. was posthumously recognized.

1993 | Vince Gill sweeps, tying Johnny Cash’s record

Photograph courtesy of the Country Music Association

Before the night of September 29, 1993, only one performer had ever taken home five trophies from a single CMA Awards. That was “The Man in Black,” Johnny Cash, and the year was 1969. Nearly a quarter century later, a virtuoso who had quietly become one of country music’s most respected artists tied the record with five wins of his own.

Vince Gill, who served as host of the CMA Awards for 12 years including 1993, cleaned house with the honors for Album of the Year, Entertainer of the Year, Male Vocalist of the Year, Song of the Year, and Vocal Event of the Year. “I’ve always operated under the theory that I don’t feel like I’m an entertainer,” a clearly humbled Gill said in his speech. “I just feel like I’m a musician and I sing songs.”

2001 | Alan Jackson’s performs “Where Were You When the World Stopped Turning”

Photograph courtesy of the Country Music Association

It hadn’t been two months since the September 11 terror attacks when Opry member Alan Jackson stood on stage at the CMA Awards and set the nation’s grief to music. His soul-bearing “Where Were You When the World Stopped Turning” precisely captured the collective disbelief and sorrow, yet the song felt deeply personal to the experiences of the listener.

Jackson was reluctant to record the song given its sensitive nature, but after some encouragement, he debuted it live at the CMA Awards. The positive response was immediate as country and pop radio stations started playing it regularly the very next day. The song earned him his first Grammy Award and is still admired today for consoling many in a dark time.