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 USCANSingleArtistReference816All Things ConsideredYankee Grey11AmazedLonestar41Anyone ElseCollin Raye11BreatheFaith Hill35Busy ManBilly Ray Cyrus1922By the BookMichael Peterson218Can't Get EnoughPatty Loveless121Crazy Little Thing Called LoveDwight Yoakam61Drive Me WildSawyer Brown21For a Little WhileTim McGraw627For You I WillAaron Tippin31God Must Have Spent a Little More Time on YouAlabama42Gone CrazyAlan Jackson2618The GreatestKenny Rogers518Hands of a Working ManTy Herndon15He Didn't Have to BeBrad Paisley1511Hello L.O.V.E.John Michael Montgomery137Hillbilly ShoesMontgomery Gentry44Hold On to MeJohn Michael Montgomery28Home to YouJohn Michael Montgomery11How Forever FeelsKenny Chesney52I Can't Get Over YouBrooks & Dunn11I Don't Want to Miss a ThingMark Chesnutt11I Love YouMartina McBride102I'll Go CrazyAndy Griggs106I'll Still Love You MoreTrisha Yearwood21I'll Think of a Reason LaterLee Ann Womack310I'm Already TakenSteve Wariner1737I'm LeavingAaron Tippin148Keepin' UpAlabama22Lesson in Leavin'Jo Dee Messina1921Lightning Does the WorkChad Brock37Little Good-ByesSHeDAISY34Little ManAlan Jackson511Lonely and GoneMontgomery Gentry1213Love Ain't Like ThatFaith Hill1925Make Up in LoveDoug Stone1624A Man Ain't Made of StoneRandy Travis1724Maybe Not TonightSammy Kershaw & Lorrie Morgan41MeanwhileGeorge Strait156Missing YouBrooks & Dunn610A Night to RememberJoe Diffie14No Place That FarSara Evans1211(Now You See Me) Now You Don'tLee Ann Womack75One Honest HeartReba McEntire310Ordinary LifeChad Brock248Ordinary LoveShane Minor11Please Remember MeTim McGraw62Pop a TopAlan Jackson61Powerful ThingTrisha Yearwood23Ready to RunDixie Chicks11Right on the MoneyAlan Jackson42The Secret of LifeFaith Hill1635She's Always RightClay Walker718She's in LoveMark Wills11Single White FemaleChely Wright208Slave to the HabitShane Minor1923Somebody's Out There WatchingThe Kinleys11Something Like ThatTim McGraw27Spirit of a Boy, Wisdom of a ManRandy Travis11Stand Beside MeJo Dee Messina1819SteamTy Herndon1620Stranger in My MirrorRandy Travis410There You Have ItBlackHawk1710This Heartache Never SleepsMark Chesnutt64Tonight the Heartache's on MeDixie Chicks25Two TeardropsSteve Wariner21UnbelievableDiamond Rio42What Do You Say to ThatGeorge Strait26Whatever You SayMartina McBride11When I Said I DoClint Black with Lisa Hartman Black1211Who Needs PicturesBrad Paisley14Wish You Were HereMark Wills97With YouLila McCann11Write This DownGeorge Strait15Wrong AgainMartina McBride66Wrong NightReba McEntire11You Had Me from HelloKenny Chesney3619You Still Shake MeDeana Carter11You Were MineDixie Chicks211You Won't Ever Be LonelyAndy Griggs27You're Beginning to Get to MeClay Walker

Singles released by Canadian artists USCANSingleArtistReference—9Ain't Nobody Like YouPatricia Conroy—8All My LifeJim Witter—14Back in Your LifeJulian Austin—8Better Off BrokenLisa Brokop—9Bit by BitJohn Landry—6Blue HorizonFarmer's Daughter503Boy Oh BoyThe Wilkinsons61Come On OverShania Twain—8Direction of LovePatricia Conroy—17Easy as 1, 2, 3The Spurs122Everytime I CryTerri Clark151Fly (The Angel Song)The Wilkinsons—9Forever in LoveShirley Myers with Duane Steele—15FreewayFarmer's Daughter—20How Do I Get There from HerGeorge Fox7019I Already FellGil Grand657I Want a ManLace—19I Wish She Was MineColin Amey3813It's a Beautiful ThingPaul Brandt—12Ivey's WallBruce Guthro—10Jumpin' Right InJim Witter—9Keep On DreamingPrairie Oyster—16Leslie's Wedding DayJoel Feeney42Man! I Feel Like a Woman!Shania Twain—12Nothing but Love (Standing in the Way)The Wilkinsons—9Running Away with YouThomas Wade—15She Ain't Gonna CryJoel Feeney—14She'll Find Someone to Love HerJamie Warren—19She's Sittin' PrettyReese Klaiber—10Shiver 'n' ShakeRick Tippe676Stuff That MattersTara Lyn Hart—9Sure Fire LoveSean Hogan82That Don't Impress Me MuchShania Twain471That's the TruthPaul Brandt—7There You WereJohn Landry—18There's More Where That Came FromJason McCoy—19Tired of Leavin'Sean Hogan—12Triple ThreatRick Tippe4715Unsung HeroTerri Clark—10What a Woman Wants to HearJamie Warren—12Who Needs the MoonChad Klinger—12Wild Wild WestChris Cummings131You've Got a WayShania Twain

Top new album releases

US CAN Album Artist Record label 18 16 Biggest Hits Johnny Cash Columbia 17 20 Greatest Hits Chris LeDoux Capitol Nashville 21 444 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