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October 25, 1999 As bluegrass music starts to take off in America, Dolly Parton releases The Grass Is Blue. The album gives her career a boost and wins the 2001 Grammy Award for Best Bluegrass Album.More

October 20, 1999 A year after nearly dying from pneumonia, Johnny Cash finds himself battling the condition again. Cash is listed in serious condition at Baptist Hospital in Nashville.

October 19, 1999 Primus issue their sixth studio album, Antipop. The song "Eclectic Electric" features guitar from James Hetfield of Metallica, and Jim Martin, formerly of Faith No More.

October 17, 1999 Steel guitarist Tommy Durden, who co-wrote Elvis Presley's "Heartbreak Hotel," dies at age 79.

October 10, 1999 Las Vegas' Grand Hotel holds an auction of several hundred thousand dollars' worth of Elvis memorabilia, including the King's wristwatch, cigar box, and his 1956 Lincoln Continental.

October 9, 1999 David Bowie, Sheryl Crow and George Michael are among the performers at NetAid, a set of three simultaneous concerts streamed live to harness the internet as a hub for activism. The shows, which are also broadcast on TV and radio, take place at Wembley Stadium, Giants Stadium and the Palais des Nations in Geneva. They go well but draw surprisingly little interest in activism, as folks would rather use their time online to find photos of Britney Spears than help eradicate third-world debt.

October 7, 1999 Garth Brooks releases an album as "Chris Gaines," a character he created that was intended for a movie. The ruse turns off many fans, and the album is Brooks' first since 1995 that fails to debut at #1, charting behind Creed's Human Clay.

October 5, 1999 After breaking up in 1983, The Who reform when Roger Daltrey announces that they will play a concert in Las Vegas.

October 4, 1999 15-year-old country music singer Jessica Andrews is honored in her native Carroll County, Tennessee, where she receives the first-ever Youth Achievement Award.

October 3, 1999 Tom Jones charts a UK #1 album for the first time in 25 years when his set Reload hits the top spot. Joining the 59-year-old Jones on the album are Robbie Williams, Stereophonics, Barenaked Ladies and the Pretenders.

October 2, 1999 Twenty-year-old Eve hits #1 in America with her debut album, Ruff Ryders' First Lady. It's the third chart-topper of 1999 for the red-hot Ruff Ryders label, following DMX' Flesh of My Flesh, Blood of My Blood and the collaborative Ruff Ryders Ryde or Die Vol. 1. Another female rapper doesn't claim the top spot until Nicki Minaj in 2012 with Pink Friday: Roman Reloaded.

September 29, 1999 Professional skateboarder Tony Hawk launches the video game Tony Hawk's Pro Skater with a punk and ska soundtrack that introduces gamers to acts like Goldfinger, Dead Kennedys, Primus, and The Vandals.More

September 28, 1999 Creed release their second album, Human Clay. It sells over 11 million copies in America thanks to songs like "With Arms Wide Open" and "Higher," but the crush of attention takes a toll on lead singer Scott Stapp, who sinks into an addiction and depression that break up the band in 2004.

September 24, 1999 Sting releases his sixth solo album, Brand New Day. Among the many collaborators is the Algerian singer Cheb Mami, who appears on "Desert Rose."

September 24, 1999 Hank Williams is the subject of the first-ever country music symposium at the Smithsonian Institution in Washington, D.C. "A Tribute To Hank Williams" begins with Lucinda Williams, Kim Richey, Kathy Mattea, and Steve Earle performing the works of the late country music godfather.

September 22, 1999 Vince Gill competes with himself in the vocal event category at the Country Music Association Awards in Nashville. Gill is up with Patty Loveless for "My Kind of Woman/My Kind of Man" and with Sara Evans for "No Place That Far."

September 21, 1999 An HBO live music show called Reverb makes its debut with performances from Alanis Morissette and Everlast.

September 19, 1999 The Dixie Chicks become the first country group to top the Billboard albums chart when Fly debuts at #1. More

September 17, 1999 Eminem's mother, Debbie Mathers-Briggs, files a lawsuit against him, claiming that his allegations in the press and on records that she was an unfit mother have ruined her life, as she can no longer get a job or a line of credit. In his song "My Name Is," Eminem raps: "I just found out my mom does more dope than I do." The case is eventually settled for $25,000.

September 10, 1999 Standin' On The Corner Park opens in Winslow, Arizona. Inspired by the city's famous mention in the Eagles song "Take It Easy," the park features a statue of a man with a guitar standing on the corner. The park quickly becomes a popular photo op for folks passing through Winslow.

September 7, 1999 Pop singer-songwriter Gracie Abrams is born in Los Angeles, California, to filmmaker JJ Abrams and producer Katie McGrath. The "I Love You, I'm Sorry" singer builds a following during the COVID-19 pandemic by livestreaming shows from her childhood bedroom over Zoom.

August 31, 1999 Led by the hit single "Ready To Run," the Dixie Chicks release their second major-label album, Fly. More

August 24, 1999 18-year-old Christina Aguilera releases her self-titled debut album, which includes three #1 hits: "Genie in a Bottle," "What a Girl Wants" and "Come On Over Baby (All I Want Is You)." It ushers in a new era of teen pop alongside her former Mickey Mouse Club star, Britney Spears.

August 18, 1999 Alanis Morissette and Tori Amos launch their 5 1/2 Weeks Tour in Ft. Lauderdale, Florida. It's sponsored by MP3.com, a hot tech company that lets users download songs for free. Morissette gets stock in the company as part of the deal.

August 17, 1999 Derek Longmuir of the Bay City Rollers is arraigned on charges of possession of illegal drugs and child pornography. He is sentenced to 300 hours of community service.

August 14, 1999 Before an in-store signing in Norridge, Illinois, the nine guys in Slipknot change into their masks and jumpsuits behind a jewelry store, and the cops show up, thinking they're going to rob the place. After they prove they're a theatrical metal band and not a crime ring, the police escort them to the signing.

August 8, 1999 It's a nu-metal moment at the Family Values Tour in Kansas City when Puddle Of Mudd frontman Wes Scantlin sneaks backstage and slips a demo tape to Fred Durst's security guard. The Limp Bizkit leader gives it a listen and signs the band to his label, Flawless Records.

July 25, 1999 Woodstock '99 comes to a fiery conclusion as the crowd loots and burns anything they can find while the Red Hot Chili Peppers play the last set. Poor conditions and a mostly collage-age crowd swelled by testosterone and nu metal have made the riot pretty much inevitable. Remarkably, there are relatively few injuries; when police arrive, the crowd seems more than happy to leave.

July 24, 1999 The rapper Treach (Anthony Criss) from Naughty by Nature ("O.P.P.") marries Pepa (Sandra Denton) of Salt-N-Pepa in a ceremony officiated by Reverend Run of Run-D.M.C., who says it's the first time a rapper has married two rappers. Among the guests are Salt, Queen Latifah and Vivica A. Fox. The couple divorce in 2001, with Pepa alleging abuse.

July 13, 1999 In support of their acclaimed synth-infused album The Soft Bulletin, The Flaming Lips embark on a "headphones tour" that combines pre-recorded material, provided to the audience through customized headsets, with the live stage show.More

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