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This is a list of notable events in country music that took place in the year 1999.
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- March 6 — George Jones, in the midst of a comeback this year, is seriously injured when he crashed his Lexus into a bridge. It is later revealed that alcohol was a factor in the accident, and he pleaded guilty to drunk driving charges.
- June — Comedian Jeff Foxworthy debuts his syndicated radio countdown show, "The Foxworthy Countdown." The radio show would end ten years later.
- September 4 — Lonestar's hit, "Amazed", spends its eighth week at No. 1 on the Billboard magazine Hot Country Singles & Tracks chart, becoming the first song to do so since Jack Greene's 1966 hit, "There Goes My Everything." In several other trade magazines, including Radio & Records, "Amazed" reigns for nine weeks, which made it the longest-lasting Number One single since 1966's "Almost Persuaded" by David Houston. By year's end, "Amazed" is gaining popularity on CHR and adult contemporary stations (in re-mixed versions, which excised the steel guitar).
- September 22 - Alan Jackson sings the chorus of George Jones' "Choices" in the middle of his performance of "Pop a Top" on the Country Music Association Awards broadcast, after TV producers required that Jones perform an abridged version, in which he refused and boycotted the show. The performance has become one of the best and most memorable moments in CMA history.
- September 28 - Garth Brooks releases In the Life of Chris Gaines, a compilation album of Brooks' alter ego, fictional Australian rock star Chris Gaines. The album was intended to be the soundtrack to a film called The Lamb, however the film was never filmed, due to financial and management problems. The album received disappointing sales in comparison to Brooks' other albums.
Singles released by American artists
Singles released by Canadian artists
Other top albums
| US | CAN | Album | Artist | Record Label |
|---|---|---|---|---|
| 47 | 16 Biggest Hits | Roy Orbison | Monument | |
| 65 | 20th Century Masters: The Millennium Collection | Conway Twitty | MCA Nashville | |
| 31 | All-Star Country Christmas | Various Artists | Hip-O | |
| 46 | Ancient Tones | Ricky Skaggs | Skaggs Family | |
| 32 | Being Human | Michael Peterson | Reprise | |
| 50 | Best of Country: 16 Original Country Hits | Various Artists | Madacy | |
| 37 | Chad Brock | Chad Brock | Warner Bros. | |
| 29 | Classic Country 1970–1974 | Various Artists | Time Life | |
| 30 | Classic Country Early '70s | Various Artists | Time Life | |
| 30 | Classic Country Late '60s | Various Artists | Time Life | |
| 34 | Closer | Susan Ashton | Capitol Nashville | |
| 37 | Country Fun | Various Artists | Warner Bros. | |
| 29 | Country Hits of the '70s | Various Artists | EMI | |
| 63 | Deryl Dodd | Deryl Dodd | Columbia | |
| 67 | Duets Volume 1 | Patsy Cline | Mercury Nashville | |
| 38 | For the Record – 43 Legendary Hits | Merle Haggard | BNA | |
| 69 | Full Western Dress | The Derailers | Sire | |
| 28 | Gettin' My Mind Right | Tim Wilson | Capitol Nashville | |
| 44 | Here's Your Christmas Album | Bill Engvall | Warner Bros. | |
| 63 | Hits and Highways Ahead | Lee Roy Parnell | Arista Nashville | |
| 45 | I've Got a Right to Cry | Mandy Barnett | Sire | |
| 44 | It's a Sorry World | Tim Wilson | Capitol Nashville | |
| 53 | John Denver Christmas | John Denver | Laserlight | |
| 48 | Juddmental | Cledus T. Judd | Razor & Tie | |
| 72 | King of the Hill Soundtrack | Various Artists | Elektra | |
| 61 | Live at Billy Bob's Texas: Motorcycle Cowboy | Merle Haggard | Smith | |
| 72 | Live with the Possum | George Jones | Asylum | |
| 38 | Make Up in Love | Doug Stone | Atlantic | |
| 63 | The Man in Black – His Greatest Hits | Johnny Cash | Legacy | |
| 61 | Old Dogs | Old Dogs | Atlantic | |
| 73 | Revolutions | The Great Divide | Atlantic | |
| 39 | Ryman Country Homecoming 1 | Various Artists | Coming Home | |
| 40 | Ryman Country Homecoming 2 | Various Artists | Coming Home | |
| 41 | Ryman Country Homecoming 3 | Various Artists | Coming Home | |
| 65 | Soldier of the Cross | Ricky Skaggs & Kentucky Thunder | Skaggs Family | |
| 70 | South Sixty-Five | South Sixty-Five | Atlantic | |
| 74 | Steve Austin's Stone Cold Country | Various Artists | Mars | |
| 43 | Super Hits | Brooks & Dunn | Arista Nashville | |
| 44 | Super Hits | Alan Jackson | Arista Nashville | |
| 73 | Suzy Bogguss | Suzy Bogguss | Platinum | |
| 30 | Tara Lyn Hart | Tara Lyn Hart | Epic | |
| 29 | There Will Come a Day | Shirley Myers | Stony Plain | |
| 30 | What I Deserve | Kelly Willis | Rykodisc | |
| 69 | Your Love Amazes Me: A Country Inspirational Collection |
Various Artists | MCA Nashville |
- February 8 – Lulu Belle (born Myrtle Eleanor Cooper), 85, one-half of the 1930s–1940s husband-and-wife duo Lulu Belle and Scotty, later a state Representative in the North Carolina Legislature.
- September 30 — Connie Eaton, 49, singer of the 1970s (cancer)
- October 2 — Danny Mayo, 49, writer of hit singles by Alabama, Confederate Railroad, Pirates of the Mississippi, and Tracy Byrd, father of songwriter Aimee Mayo (heart attack)
- December 17 — Rex Allen, 78, "The Arizona Cowboy" and traveling rodeo performer.
- December 20 — Hank Snow, 85, "The Singing Ranger," best known for "I'm Movin' On."
Bluegrass Music Hall of Fame inductees
Country Music Hall of Fame inductees
- Johnny Bond (1915–1978)
- Dolly Parton (born 1946)
- Conway Twitty (1933–1993)
Canadian Country Music Hall of Fame inductees
Grammy Awards
- Best Female Country Vocal Performance — "Man! I Feel Like a Woman!", Shania Twain
- Best Male Country Vocal Performance — "Choices", George Jones
- Best Country Performance by a Duo or Group with Vocal — "Ready to Run", Dixie Chicks
- Best Country Collaboration with Vocals — "After the Gold Rush", Emmylou Harris, Dolly Parton and Linda Ronstadt
- Best Country Instrumental Performance — "Bob's Breakdowns", Tommy Allsup, Asleep at the Wheel, Floyd Domino, Larry Franklin, Vince Gill and Steve Wariner
- Best Country Song — "Come on Over", Shania Twain and Robert John "Mutt" Lange
- Best Country Album — Fly, Dixie Chicks
- Best Bluegrass Album — Ancient Tones, Ricky Skaggs & Kentucky Thunder
Juno Awards
- Best Country Male Artist — Paul Brandt
- Best Country Female Artist — Shania Twain
- Best Country Group or Duo — The Rankins
Academy of Country Music
- Entertainer of the Year — Shania Twain
- Song of the Year — "Amazed", Marv Green, Aimee Mayo
- Single of the Year — "Amazed", Lonestar
- Album of the Year — Fly, Dixie Chicks
- Top Male Vocalist — Tim McGraw
- Top Female Vocalist — Faith Hill
- Top Vocal Duo or Group — Dixie Chicks
- Top New Male Vocalist — Brad Paisley
- Top New Female Vocalist — Jessica Andrews
- Top New Vocal Duo or Group — Montgomery Gentry
- Video of the Year — "Breathe", Faith Hill (Director: Lili Fini Zanuck)
- Vocal Event of the Year — "When I Said I Do", Clint Black with Lisa Hartman Black
ARIA Awards
(presented in Sydney on October 12, 1999)
Canadian Country Music Association
- CMT Maple Leaf Foods Fans' Choice Award — Shania Twain
- Male Artist of the Year — Paul Brandt
- Female Artist of the Year — Shania Twain
- Group or Duo of the Year — The Wilkinsons
- SOCAN Song of the Year — "26 Cents", Steve Wilkinson, William Wallace
- Single of the Year — "26 Cents", The Wilkinsons
- Album of the Year — Nothing but Love, The Wilkinsons
- Top Selling Album — Wide Open Spaces, Dixie Chicks
- Video of the Year — "That Don't Impress Me Much", Shania Twain
- Wrangler Rising Star Award — The Wilkinsons
- Vocal/Instrumental Collaboration of the Year — "From This Moment On", Shania Twain and Bryan White
Country Music Association
- Entertainer of the Year — Shania Twain
- Song of the Year — "This Kiss", Robin Lerner, Annie Roboff and Beth Nielsen Chapman
- Single of the Year — "Wide Open Spaces", Dixie Chicks
- Album of the Year — A Place in the Sun, Tim McGraw
- Male Vocalist of the Year — Tim McGraw
- Female Vocalist of the Year — Martina McBride
- Vocal Duo of the Year — Brooks & Dunn
- Vocal Group of the Year — Dixie Chicks
- Horizon Award — Jo Dee Messina
- Music Video of the Year — "Wide Open Spaces", Dixie Chicks (Director: Thom Oliphant)
- Vocal Event of the Year — "My Kind of Woman, My Kind of Man", Vince Gill and Patty Loveless
- Musician of the Year — Randy Scruggs
RPM Big Country Awards
- Canadian Country Artist of the Year — Shania Twain
- Best Country Album — Nothing but Love, The Wilkinsons
- Best Country Single — "26 Cents", The Wilkinsons
- Male Artist of the Year — Paul Brandt
- Female Artist of the Year — Shania Twain
- Group of the Year — The Wilkinsons
- Outstanding New Male Artist — Gil Grand
- Outstanding New Female Artist — Stephanie Beaumont
- Outstanding New Group or Duo — The Johner Brothers
- Canadian Country Video — "26 Cents", The Wilkinsons
- Top Country Composer(s) — Bruce Guthro
- Whitburn, Joel, "Top Country Songs 1944–2005 – 6th Edition." 2005.
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