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Top 10 Country Grammy Awards Moments

Dixie Chicks
Vince Bucci, Getty Images

Since 1959, “Music’s Biggest Night” — the Grammy Awards — has featured the world’s top artists in every musical genre, from pop and R&B to country, bluegrass, folk and Americana. And there have been a slew of memorable Grammys moments involving some of The Boot’s favorite artists.

From LeAnn Rimes‘ win at the tender age of 14 to the Dixie Chicks‘ surprising sweep in 2007 — not to mention the woman who has more Grammys than any other and some truly amazing performances — these are our Top 10 country moments from Grammy Awards history.


Lady Antebellum Garner Five Grammys

54th Annual Grammy Awards (2011)



Lady Antebellum gave country music a huge moment to shine at the 54th annual Grammy Awards in 2011. The trio nabbed two of the evening’s biggest awards, the all-genre Record of the Year and Song of the Year, for their second studio album, Need You Now, and its title track, respectively. Lady A also performed at the ceremony and picked up Best Country Album, Best Country Song and Best Country Performance By a Duo or Group With Vocals, walking away with five of the six awards for which they’d been nominated and paving the way for their next album, Own the Night. Like Need You Now, the record debuted at the top of the Billboard 200 when it was released in September of 2011.



Carrie Underwood Wins Best New Artist

49th Annual Grammy Awards (2007)



Carrie Underwood is undoubtedly the biggest star from the singing competition show American Idol, and she proved it at the 49th annual Grammy Awards in 2007, beating out Corinne Bailey Rae, James Blunt, Chris Brown and Imogen Heap for Best New Artist. Underwood was only the second country artist in Grammys history, and the first in a decade, to win the accolade. That year, she also nabbed Best Female Country Vocal Performance, for “Jesus, Take the Wheel.” The trophies would be the first of several Grammys for the talented songstress.



Glen Campbell Wins Album of the Year

11th Annual Grammy Awards (1969)



In 1969, well-loved country artist Glen Campbell showed everyone that country music stars could play with the big boys. At the 11th annual Grammy Awards, he took home the trophy for Album of the Year, for By the Time I Get to Phoenix, and beat out legendary artists like the Beatles, Simon & Garfunkel, José Feliciano and Richard Harris. The “Wichita Lineman” hitmaker had won four Grammys the previous year.

Kevin Winter, Getty Images
Kevin Winter, Getty Images


Taylor Swift, Miley Cyrus Perform “Fifteen”

51st Annual Grammy Awards (2009)



Remember when Taylor Swift and Miley Cyrus were just teenagers? We barely do either, but the two singers converged at the 51st annual Grammy Awards in 2009 for an innocent, impactful and inspirational duet of Swift’s hit “Fifteen,” which she wrote when she was still a fresh-faced teen herself. Their performance was a sweet moment for the Grammys — and now, both women have gone on to be two of the world’s biggest superstars.



Dolly Parton Receives Most Grammy Nominations of Any Country Artist



Did you know that Dolly Parton has received the most Grammy nominations of any country artist? Her first came at the 12th annual Grammy Awards in 1970, when “Just Someone I Used to Know,” a with Porter Wagoner, was nominated for Best Country Vocal Performance By a Duo or Group; her most recent nomination was in 2014 at the 56th annual ceremony, for her duet “You Can’t Make Old Friends” with Kenny Rogers. With 46 nods to her name, Miss Dolly is the second-most nominated female artist in Grammys history, below only pop queen Beyonce.

Kevin Winter/Hulton Archive, Getty Images
Kevin Winter/Hulton Archive, Getty Images


Alison Krauss Awarded Most Grammys of Any Female Artist



There’s only one woman who has received a total of 27 Grammy Awards, and that woman is bluegrass aficionado Alison Krauss. Her first piece of hardware was awarded in 1991, at the 33rd annual ceremony, when she received the award for Best Bluegrass Recording, for I’ve Got That Old Feeling; Krauss’ most recent Grammy Award came at the 54th annual Grammy Awards in 2012, again for Best Bluegrass Album, for Paper Airplane. Among all artists, the established singer-songwriter is tied with Quincy Jones for second place for the most Grammys won, behind Chicago Symphony Orchestra conductor Sir Georg Solti, who’s received 31 awards.

Kevork Djansezian, Getty Images
Kevork Djansezian, Getty Images


Willie Nelson Takes Home Grammy Legend Award

32nd Annual Grammy Awards (1990)



In 1990, at the 32nd annual Grammy Awards, Willie Nelson was among the first class of recipients of the prestigious Grammy Legend Award, which recognizes “ongoing contributions and influence in the recording field.” Andrew Lloyd Webber, Liza Minelli and Smokey Robinson also received the award that year. Johnny Cash is the only other country artist to have received a Grammy Legend Award; his was given the following year, at the 33rd annual ceremony.

Kevork Djansezian, Getty Images
Kevork Djansezian, Getty Images


The Highwaymen Regroup for Grammy Awards Performance

56th Annual Grammy Awards (2014)



The year 1984 was a memorable one in country music, because it saw four of the genre’s biggest superstars — Waylon Jennings, Willie Nelson, Johnny Cash and Kris Kristofferson — come together as a supergroup. That year, the quartet recorded “Highwayman,” a single that birthed an album, inspired the quartet’s name and led to over 10 years of them hitting the stage together. Nearly 20 years later, the 56th annual Grammy Awards in 2014 were made extra special when the legendary group (sans Cash and Jennings, who passed away in 2003 and 2002, respectively) regrouped for a special performance: Kristofferson and Nelson performed “Highwayman,” were joined by Merle Haggard and Blake Shelton for “Okie From Muskogee” and then launched into a ragged but spirited rendition of “Mamas, Don’t Let Your Babies Grow up to Be Cowboys” to finish things off.



14-Year-Old LeAnn Rimes Wins Best New Artist

39th Annual Grammy Awards (1997)



On Sunday nights, most 14-year-olds are thinking about what they’ll say to the cute boy at school the next day — not planning an acceptance speech for the Grammy Awards! But LeAnn Rimes made history at the 39th annual Grammy Awards in 1997. With a voice that sounded well beyond her 14 years of age, she nabbed the all-genre Best New Artist trophy, setting records as the youngest Grammy winner and the first country act to win Best New Artist. Rimes beat out fan-favorite artists Jewel, Garbage, No Doubt and the Tony Rich Project in the category; she also picked up Best Female Country Vocal Performance, for her song “Blue.”

Jason Merritt, Getty Images
Jason Merritt, Getty Images


Dixie Chicks Sweep the Grammys

49th Annual Grammy Awards (2007)



After Dixie Chicks member Natalie Maines dissed President Bush at a 2003 concert in London, England, the trio was shunned by the country music industry overnight. So it was unclear how they would fare at the 49th annual Grammy Awards in 2007, where they were nominated for five awards: the all-genre Album of the Year, as well as Best Country Album, for their 2006 record Taking the Long Way, and Record of the Year, Song of the Year and Best Country Performance By a Duo or Group With Vocals, for “Not Ready to Make Nice.” However, the trio cleaned up at the Grammys, winning all five of their categories. It was the first Album of the Year, Record of the Year and Song of the Year sweep in 14 years.


NEXT: 10 Country Music Risk-Takers

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