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1999 in country music
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This is a list of notable events in country music that took place in the year 1999.
Events
- 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.
Top hits of the year
Singles released by American artists
| US | CAN | Single | Artist | Reference |
|---|---|---|---|---|
| 8 | 16 | All Things Considered | Yankee Grey | |
| 1 | 1 | Amazed | Lonestar | |
| 4 | 1 | Anyone Else | Collin Raye | |
| 1 | 1 | Breathe | Faith Hill | |
| 3 | 5 | Busy Man | Billy Ray Cyrus | |
| 19 | 22 | By the Book | Michael Peterson | |
| 21 | 8 | Can't Get Enough | Patty Loveless | |
| 12 | 1 | Crazy Little Thing Called Love | Dwight Yoakam | |
| 6 | 1 | Drive Me Wild | Sawyer Brown | |
| 2 | 1 | For a Little While | Tim McGraw | |
| 6 | 27 | For You I Will | Aaron Tippin | |
| 3 | 1 | God Must Have Spent a Little More Time on You | Alabama | |
| 4 | 2 | Gone Crazy | Alan Jackson | |
| 26 | 18 | The Greatest | Kenny Rogers | |
| 5 | 18 | Hands of a Working Man | Ty Herndon | |
| 1 | 5 | He Didn't Have to Be | Brad Paisley | |
| 15 | 11 | Hello L.O.V.E. | John Michael Montgomery | |
| 13 | 7 | Hillbilly Shoes | Montgomery Gentry | |
| 4 | 4 | Hold On to Me | John Michael Montgomery | |
| 2 | 8 | Home to You | John Michael Montgomery | |
| 1 | 1 | How Forever Feels | Kenny Chesney | |
| 5 | 2 | I Can't Get Over You | Brooks & Dunn | |
| 1 | 1 | I Don't Want to Miss a Thing | Mark Chesnutt | |
| 1 | 1 | I Love You | Martina McBride | |
| 10 | 2 | I'll Go Crazy | Andy Griggs | |
| 10 | 6 | I'll Still Love You More | Trisha Yearwood | |
| 2 | 1 | I'll Think of a Reason Later | Lee Ann Womack | |
| 3 | 10 | I'm Already Taken | Steve Wariner | |
| 17 | 37 | I'm Leaving | Aaron Tippin | |
| 14 | 8 | Keepin' Up | Alabama | |
| 2 | 2 | Lesson in Leavin' | Jo Dee Messina | |
| 19 | 21 | Lightning Does the Work | Chad Brock | |
| 3 | 7 | Little Good-Byes | SHeDAISY | |
| 3 | 4 | Little Man | Alan Jackson | |
| 5 | 11 | Lonely and Gone | Montgomery Gentry | |
| 12 | 13 | Love Ain't Like That | Faith Hill | |
| 19 | 25 | Make Up in Love | Doug Stone | |
| 16 | 24 | A Man Ain't Made of Stone | Randy Travis | |
| 17 | 24 | Maybe Not Tonight | Sammy Kershaw & Lorrie Morgan | |
| 4 | 1 | Meanwhile | George Strait | |
| 15 | 6 | Missing You | Brooks & Dunn | |
| 6 | 10 | A Night to Remember | Joe Diffie | |
| 1 | 4 | No Place That Far | Sara Evans | |
| 12 | 11 | (Now You See Me) Now You Don't | Lee Ann Womack | |
| 7 | 5 | One Honest Heart | Reba McEntire | |
| 3 | 10 | Ordinary Life | Chad Brock | |
| 24 | 8 | Ordinary Love | Shane Minor | |
| 1 | 1 | Please Remember Me | Tim McGraw | |
| 6 | 2 | Pop a Top | Alan Jackson | |
| 6 | 1 | Powerful Thing | Trisha Yearwood | |
| 2 | 3 | Ready to Run | Dixie Chicks | |
| 1 | 1 | Right on the Money | Alan Jackson | |
| 4 | 2 | The Secret of Life | Faith Hill | |
| 16 | 35 | She's Always Right | Clay Walker | |
| 7 | 18 | She's in Love | Mark Wills | |
| 1 | 1 | Single White Female | Chely Wright | |
| 20 | 8 | Slave to the Habit | Shane Minor | |
| 19 | 23 | Somebody's Out There Watching | The Kinleys | |
| 1 | 1 | Something Like That | Tim McGraw | |
| 2 | 7 | Spirit of a Boy, Wisdom of a Man | Randy Travis | |
| 1 | 1 | Stand Beside Me | Jo Dee Messina | |
| 18 | 19 | Steam | Ty Herndon | |
| 16 | 20 | Stranger in My Mirror | Randy Travis | |
| 4 | 10 | There You Have It | BlackHawk | |
| 17 | 10 | This Heartache Never Sleeps | Mark Chesnutt | |
| 6 | 4 | Tonight the Heartache's on Me | Dixie Chicks | |
| 2 | 5 | Two Teardrops | Steve Wariner | |
| 2 | 1 | Unbelievable | Diamond Rio | |
| 4 | 2 | What Do You Say to That | George Strait | |
| 2 | 6 | Whatever You Say | Martina McBride | |
| 1 | 1 | When I Said I Do | Clint Black with Lisa Hartman Black | |
| 12 | 11 | Who Needs Pictures | Brad Paisley | |
| 1 | 4 | Wish You Were Here | Mark Wills | |
| 9 | 7 | With You | Lila McCann | |
| 1 | 1 | Write This Down | George Strait | |
| 1 | 5 | Wrong Again | Martina McBride | |
| 6 | 6 | Wrong Night | Reba McEntire | |
| 1 | 1 | You Had Me from Hello | Kenny Chesney | |
| 36 | 19 | You Still Shake Me | Deana Carter | |
| 1 | 1 | You Were Mine | Dixie Chicks | |
| 2 | 11 | You Won't Ever Be Lonely | Andy Griggs | |
| 2 | 7 | You're Beginning to Get to Me | Clay Walker |
Singles released by Canadian artists
| US | CAN | Single | Artist | Reference |
|---|---|---|---|---|
| — | 9 | Ain't Nobody Like You | Patricia Conroy | |
| — | 8 | All My Life | Jim Witter | |
| — | 14 | Back in Your Life | Julian Austin | |
| — | 8 | Better Off Broken | Lisa Brokop | |
| — | 9 | Bit by Bit | John Landry | |
| — | 6 | Blue Horizon | Farmer's Daughter | |
| 50 | 3 | Boy Oh Boy | The Wilkinsons | |
| 6 | 1 | Come On Over | Shania Twain | |
| — | 8 | Direction of Love | Patricia Conroy | |
| — | 17 | Easy as 1, 2, 3 | The Spurs | |
| 12 | 2 | Everytime I Cry | Terri Clark | |
| 15 | 1 | Fly (The Angel Song) | The Wilkinsons | |
| — | 9 | Forever in Love | Shirley Myers with Duane Steele | |
| — | 15 | Freeway | Farmer's Daughter | |
| — | 20 | How Do I Get There from Her | George Fox | |
| 70 | 19 | I Already Fell | Gil Grand | |
| 65 | 7 | I Want a Man | Lace | |
| — | 19 | I Wish She Was Mine | Colin Amey | |
| 38 | 13 | It's a Beautiful Thing | Paul Brandt | |
| — | 12 | Ivey's Wall | Bruce Guthro | |
| — | 10 | Jumpin' Right In | Jim Witter | |
| — | 9 | Keep On Dreaming | Prairie Oyster | |
| — | 16 | Leslie's Wedding Day | Joel Feeney | |
| 4 | 2 | Man! I Feel Like a Woman! | Shania Twain | |
| — | 12 | Nothing but Love (Standing in the Way) | The Wilkinsons | |
| — | 9 | Running Away with You | Thomas Wade | |
| — | 15 | She Ain't Gonna Cry | Joel Feeney | |
| — | 14 | She'll Find Someone to Love Her | Jamie Warren | |
| — | 19 | She's Sittin' Pretty | Reese Klaiber | |
| — | 10 | Shiver 'n' Shake | Rick Tippe | |
| 67 | 6 | Stuff That Matters | Tara Lyn Hart | |
| — | 9 | Sure Fire Love | Sean Hogan | |
| 8 | 2 | That Don't Impress Me Much | Shania Twain | |
| 47 | 1 | That's the Truth | Paul Brandt | |
| — | 7 | There You Were | John Landry | |
| — | 18 | There's More Where That Came From | Jason McCoy | |
| — | 19 | Tired of Leavin' | Sean Hogan | |
| — | 12 | Triple Threat | Rick Tippe | |
| 47 | 15 | Unsung Hero | Terri Clark | |
| — | 10 | What a Woman Wants to Hear | Jamie Warren | |
| — | 12 | Who Needs the Moon | Chad Klinger | |
| — | 12 | Wild Wild West | Chris Cummings | |
| 13 | 1 | You've Got a Way | Shania Twain |
Top new album releases
| US | CAN | Album | Artist | Record label |
|---|---|---|---|---|
| 18 | *[16 Biggest Hits](16-biggest-hits-johnny-cash-album)* | Johnny Cash | Columbia | |
| 17 | *20 Greatest Hits* | Chris LeDoux | Capitol Nashville | |
| 21 | *[444](444-charlie-major-album)* | Charlie Major | Dead Reckoning | |
| 69 | 3 | *A&E Biography* | Kenny Rogers | Capitol Nashville |
| 2 | 2 | *Always Never the Same* | George Strait | MCA Nashville |
| 26 | 10 | *The Austin Sessions* | Kris Kristofferson | Atlantic |
| 15 | *The Best of Farmer's Daughter* | Farmer's Daughter | Universal | |
| 1 | 1 | *Breathe* | Faith Hill | Warner Bros. |
| 6 | *Classics* | Patty Loveless | Epic | |
| 30 | 8 | *CMT All Access – Girls Night Out* | Sara Evans, Martina McBride, | |
| Mindy McCready & Lorrie Morgan | RCA Nashville | |||
| 5 | 8 | *Cold Hard Truth* | George Jones | Asylum |
| 5 | *Country Heat 2000* | Various Artists | BMG | |
| 7 | 7 | *D'lectrified* | Clint Black | RCA Nashville |
| 10 | 9 | *Drive Me Wild* | Sawyer Brown | Curb |
| 3 | 5 | *Emotion* | Martina McBride | RCA Nashville |
| 5 | 5 | *Everywhere We Go* | Kenny Chesney | BNA |
| 1 | 1 | *Fly* | Dixie Chicks | Monument |
| 5 | 5 | *Forget About It* | Alison Krauss | Rounder |
| 1 | *Garth Brooks and the Magic of Christmas* | Garth Brooks | Capitol Nashville | |
| 24 | *The Grass Is Blue* | Dolly Parton | Blue Eye | |
| 17 | *Greatest Bits* | Jeff Foxworthy | Warner Bros. | |
| 2 | *Greatest Hits* | Chris Gaines | Capitol | |
| 12 | *The Greatest Hits Collection* | Michelle Wright | Arista | |
| 24 | *Heart Shaped World* | Jessica Andrews | DreamWorks Nashville | |
| 16 | 11 | *Home to You* | John Michael Montgomery | Atlantic |
| 13 | *How Big a Boy Are Ya? Volume 5* | Roy D. Mercer | Virgin Nashville | |
| 16 | *How Big a Boy Are Ya? Volume 6* | Roy D. Mercer | Virgin Nashville | |
| 9 | 8 | *How Do You Like Me Now?!* | Toby Keith | DreamWorks Nashville |
| 7 | *How Lucky I Am* | Bryan White | Asylum | |
| 6 | 6 | *I Don't Want to Miss a Thing* | Mark Chesnutt | Decca Nashville |
| 17 | 13 | *I'm Not So Tough* | Mindy McCready | BNA |
| 21 | *In Spite of Ourselves* | John Prine | Oh Boy | |
| 11 | *It's Christmas Time* | Elvis Presley | RCA | |
| 20 | *It's About Time* | Tracy Byrd | RCA Nashville | |
| 70 | 14 | *It's About Time* | Julie Reeves | Virgin Nashville |
| 5 | *Keepers: Greatest Hits* | Tracy Byrd | MCA Nashville | |
| 17 | 27 | *Keith Urban* | Keith Urban | Capitol Nashville |
| 17 | *Lace* | Lace | 143 | |
| 10 | 5 | *Last Chance for a Thousand Years: | ||
| Dwight Yoakam's Greatest Hits from the 90's* | Dwight Yoakam | Reprise | ||
| 1 | 2 | *LeAnn Rimes* | LeAnn Rimes | Curb |
| 24 | 21 | *The Life of the Party* | Neal McCoy | Giant |
| 7 | 14 | *Live in Texas* | Lyle Lovett | MCA Nashville |
| 5 | 23 | *Live, Laugh, Love* | Clay Walker | Giant |
| 3 | 2 | *Lonely Grill* | Lonestar | BNA |
| 14 | *Love in the Real World* | Sherrié Austin | Arista Nashville | |
| 15 | 11 | *A Man Ain't Made of Stone* | Randy Travis | DreamWorks Nashville |
| 7 | *Maybe Not Tonight* | Sammy Kershaw | Mercury Nashville | |
| 10 | *Merry Christmas Wherever You Are* | George Strait | MCA Nashville | |
| 9 | *More...* | Trace Adkins | Capitol Nashville | |
| 19 | 14 | *The Mountain* | Steve Earle & Del McCoury Band | E-Squared |
| 8 | *My Heart* | Lorrie Morgan | BNA | |
| 7 | *New Country 6* | Various Artists | Warner | |
| 23 | 25 | *A Night to Remember* | Joe Diffie | Epic |
| 4 | *Party Doll and Other Favorites* | Mary Chapin Carpenter | Columbia | |
| 63 | 21 | *The Pilgrim* | Marty Stuart | MCA Nashville |
| 1 | 2 | *A Place in the Sun* | Tim McGraw | Curb |
| 60 | 21 | *Play* | David Ball | Warner Bros. |
| 24 | *Ride with Bob* | Asleep at the Wheel | DreamWorks Nashville | |
| 10 | *The Secret of Giving: A Christmas Collection* | Reba McEntire | MCA Nashville | |
| 6 | 8 | *She Rides Wild Horses* | Kenny Rogers | Dreamcatcher |
| 15 | 16 | *Single White Female* | Chely Wright | MCA Nashville |
| 9 | 13 | *Smoke Rings in the Dark* | Gary Allan | MCA Nashville |
| 5 | 9 | *So Good Together* | Reba McEntire | MCA Nashville |
| 5 | 10 | *Something in the Air* | Lila McCann | Asylum |
| 7 | *Stampede Country* | Various Artists | Sony | |
| 14 | *Steam* | Ty Herndon | Epic | |
| 21 | *Stormy* | Hank Williams, Jr. | Curb | |
| 45 | 13 | *Super Colossal Smash Hits of the 90's: | ||
| The Best of The Mavericks* | The Mavericks | Mercury Nashville | ||
| 21 | *Superstar Country Hits* | Various Artists | UTV | |
| 10 | 4 | *Tattoos & Scars* | Montgomery Gentry | Columbia |
| 56 | 1 | *That's the Truth* | Paul Brandt | Reprise |
| 6 | 6 | *Tight Rope* | Brooks & Dunn | Arista Nashville |
| 4 | 4 | *Trio II* | Dolly Parton, Linda Ronstadt | |
| & Emmylou Harris | Asylum | |||
| 5 | 5 | *Twentieth Century* | Alabama | RCA Nashville |
| 6 | 6 | *Two Teardrops* | Steve Wariner | Capitol Nashville |
| 2 | 4 | *Under the Influence* | Alan Jackson | Arista Nashville |
| 41 | 19 | *Untamed* | Yankee Grey | Monument |
| 6 | *Western Wall: The Tucson Sessions* | Linda Ronstadt & Emmylou Harris | Asylum | |
| 4 | 6 | *What a Wonderful World* | Anne Murray | StraightWay |
| 6 | 4 | *The Whole SHeBANG* | SHeDAISY | Lyric Street |
| 13 | 13 | *Who Needs Pictures* | Brad Paisley | Arista Nashville |
| 43 | 12 | *Wildest Dreams* | John Berry | Lyric Street |
| 15 | 11 | *You Won't Ever Be Lonely* | Andy Griggs | RCA Nashville |
Other top albums
| US | CAN | Album | Artist | Record label |
|---|---|---|---|---|
| 47 | *[16 Biggest Hits](16-biggest-hits-roy-orbison-album)* | 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 |
Births
- May 3 – Ella Langley, rising singer-songwriter of the 2020s ("You Look Like You Love Me")
- November 5 – Tucker Wetmore, country music singer-songwriter of the 2020s ("Wind Up Missin' You")
Deaths
- 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.
- July 29- Anita Carter, 66, member of the Carter family
- 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."
Hall of Fame inductees
Bluegrass Music Hall of Fame inductees
- Kenny Baker
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
- Ronnie Prophet
- Walt Grealis
Major awards
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)
- Best Country Album - The Captain (Kasey Chambers)
- ARIA Hall of Fame - Jimmy Little
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
Hollywood Walk of Fame
Stars who were honored in 1999
Patsy Cline, Freddy Fender, and Charley Pride
Other links
- Country Music Association
- Inductees of the Country Music Hall of Fame
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