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.

  • 10

    Lady A Garner Five Grammys

    54th Annual Grammy Awards (2011)

    Then known as Lady Antebellum, Lady A 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.

  • 9

    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 artist.

  • 8

    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
  • 7

    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.

  • 6

    'The Joke' Catapults Brandi Carlile Into the Spotlight

    61st Annual Grammy Awards (2019)

    Brandi Carlile performed at the Grammy Awards for the first time ever in 2019 -- and what a performance it was! After winning three trophies during the pre-telecast Premiere Ceremony, she took the stage during the live ceremony to sing and play “The Joke,” one of the standout tracks on her lauded album By the Way, I Forgive You. Fans who didn't know who Carlile is were immediately converted, and those who do appreciate her emotional, evocative singing and writing were stunned beyond belief. The high notes soared, the crowd was loving it, and it’s hard to believe that there was a dry eye in the house by the time she was through.

  • 5

    Kacey Musgraves Wins Album of the Year

    61st Annual Grammy Awards (2019)

    In a stunning finale to the 2019 Grammy Awards, Kacey Musgraves took home the all-genre Album of the Year trophy, besting Janelle Monae, Post Malone, Brandi Carlile and more. Despite having won Best Country Album, Best Country Song and Best Country Solo Performance earlier in the event, Musgraves looked genuinely shocked when she headed to the stage to accept her award, for her acclaimed 2018 album Golden Hour.

  • 4

    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.

    Olivier Douliery-Pool, Getty Images
  • 3

    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.

    Getty Images
  • 2

    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."

    Rick Diamond, Getty Images
  • 1

    The 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.

    Vince Bucci, Getty Images