January

• January 7
  • After eight years of marriage, musician husband Rod Stewart and supermodel wife Rachel Hunter announce their separation.
  • Paul McCartney attends the launch of his daughter Heather's first housewares collection in Georgia.
• January 11 – During the American Music Awards, Billy Joel is awarded the Special Award of Merit for his "inspired songwriting skills" and "exciting showmanship."
• January 12
  • Britney Spears releases her hit album ...Baby One More Time. The album is the second best-selling album of the 90s in the US and the third best-selling album of the 90s worldwide. It also enters the list of the top 20 best-selling albums of all time.
  • Fredrik Johansson is fired from Dark Tranquillity.^[1]
• January 15–31 – After a short hiatus in 1998, the Big Day Out festival returns to Australia and New Zealand, headlined by Hole and Marilyn Manson.^[2]
• January 21 – A&M Records is shut down and merged into the Universal Music Group umbrella label Interscope Geffen A&M. It would be relaunched in 2007.
• January 22 – German industrial band KMFDM announces that it has disbanded.
• January 28 – Kirk Franklin performs at the Baltimore Arena in Baltimore, Maryland for the video recording of "The Nu Nation Tour" featuring CeCe Winans, Trin-i-Tee 5:7 and Crystal Lewis
• January 30 – Britney Spears' hit album and single ...Baby One More Time both hit number one on the Billboard Charts. This is her first album (and song) to achieve this. The album spent 6 weeks on number 1 and a total of 103 weeks on the Billboard 200 Charts. It's number 16 on the Billboard list "Best Female Albums of all time" and number 41 on the Billboard list "Best Albums of all time". The single "...Baby One More Time" spent 2 consecutive weeks on number one on the Billboard Hot 100 and a total of 32 weeks on that same list.

February

• February 9 – NSYNC release their third single from their debut album, "(God Must Have Spent) A Little More Time on You", which peaks in the top 10 on the Pop charts.
• February 10 – Iron Maiden announces that singer Bruce Dickinson and guitarist Adrian Smith have rejoined the band.
• February 14 – Elton John appears as himself in a special episode of the animated series The Simpsons.
• February 15 – "Rolling Stones Day" is declared in Minnesota by Governor (and former Rolling Stones bodyguard) Jesse Ventura.
• February 19 – Marilyn Manson files a defamation countersuit against former Spin Magazine editor Craig Marks, in response to a multimillion-dollar lawsuit that Marks filed in January against the singer, the record label Nothing/Interscope, and Manson's bodyguard agency.
• February 20 – Trace Adkins performs his first concert following surgery for tendon damage and a broken ankle. Contrary to doctor's orders, Adkins does not remain seated during the performance.
• February 22 – In Los Angeles, California, Stevie Wonder is honored as the 1999 MusiCares Person of the Year.^[3]
• February 23 – Eminem releases his second studio album and major-label debut, The Slim Shady LP. It debuts at number two on the Billboard 200, selling over 200,000 copies in its first week. It remains on the Billboard 200 for 100 weeks.
• February 24 – Lauryn Hill makes history at the 1999 Grammy Awards by being the first female artist to win five Grammys in one night.
• February 25 – The Artist Formerly Known as Prince files a lawsuit against nine Web sites for copyright and trademark infringement, claiming that the websites sell bootlegged recordings and offer unauthorized song downloads.

March

• March 1 – Sony Music Distribution raises wholesale prices on audio compact discs by 8 US cents.
• March 2
  • Cher's song "Believe" reaches number one on the Billboard Hot 100, making Cher the oldest female artist (at the age of 52) to perform this feat. Cher also set the record for the longest hit-making career span, with 33 years between the release of her first and last Billboard Hot 100 #1 singles (1965 and 1999).
  • The House of Blues in Paradise, Nevada at the Mandalay Bay Resort. Bob Dylan performs a concert at the club and is joined by U2's lead singer Bono for an encore of "Knockin' on Heaven's Door".
• March 5 – Trauma Records files a $40 million breach-of-contract lawsuit against the members of Bush for failing to deliver a new album.
• March 6 – A 67-year-old George Jones is seriously injured in a car accident while on his way home. Jones' Lexus crashed into a bridge at about 1:30 p.m. It is later revealed that alcohol was a factor in the accident.
• March 15 – Marilyn Manson is injured when he slips and falls during a concert at the Great Western Forum in Inglewood, California. Manson's performance is cut short.
• March 16 – The Recording Industry Association of America introduces a new certification level, Diamond, for albums or singles selling ten million units.
• March 17 – Namie Amuro's mother Emiko Taira is murdered.
• March 21 – Irish girl band B*Witched score their fourth consecutive #1 with "Blame It On The Weatherman" on the UK singles chart. They become the first band to have all their first four singles enter at the top simultaneously and set a new record. It is broken a year later by Irish boy band Westlife.
• March 23 – Green Day release "Nice Guys Finish Last", the lead track as well as the fourth and final single off their 1997 album Nimrod, and was their last single to be released in the 20th century.
• March 27 – The Bee Gees end their One Night Only tour in Sydney, Australia.

April

• April 10 – A charity tribute, the Concert for Linda McCartney is held at the Royal Albert Hall in London. Here, There and Everywhere: A Concert For Linda, features performances by Paul McCartney, Chrissie Hynde of the Pretenders, Elvis Costello, Sinéad O'Connor, and George Michael. Proceeds raised at the event went to animal rights causes.
• April 19 – Neil Young performs at Madison Square Garden in New York City. Due to a mistake by a Madison Square Garden staff member, the marquee read "Bob Dylan, Tonight at 8pm". Young jokingly introduced one of his guitar players as Bob Dylan during the show.
• April 20
  • Billy Joel performs at Meadowlands in New Jersey. Joel announces that this would be his last public pop music concert. Joel also announces plans on devoting his future efforts to classical music.
  • The Columbine High School massacre takes place in Jefferson County, Colorado, sparking a widespread moral panic that ultimately tries to place the blame on violent media, including music perceived to be violent and/or connected to the goth culture. American rocker Marilyn Manson receives the brunt of the blame despite evidence that neither of the shooters were fans of his. Manson then withdraws, only to address the issue in the form of his fourth studio album. The finger is also pointed at German industrial metal acts Rammstein and KMFDM, of whom the shooters were fans. This sensationalism gradually wanes in the years following, and all three music acts ironically achieve more mainstream acceptance in the U.S. than they had prior to the massacre. Christian Contemporary Music artists respond to the concept that Atheism caused the shooting and in particular the Cassie Bernall urban legend (about a girl who was initially believed to have been shot in the head for answering "yes" when perpetrator Eric Harris asked her if she believed in God) with songs such as "A New Hope" by Five Iron Frenzy, about a band member's sister who had been trapped in the choir room returning to school after the shooting, and "This Is Your Time" by Michael W. Smith, a direct response to the Cassie Bernall story.
• April 26 – Musician and former bandleader of The Sound, Adrian Borland, commits suicide in London.
• April 28 – Tom Petty and the Heartbreakers receive a star on the Hollywood Walk of Fame.
• April 30 – Columbine High School massacre: Aerosmith visits Columbine High School shooting victim Lance Kirklin in a Colorado hospital before a concert in Denver, Colorado. Kirklin was one of 24 wounded in the April 20 shooting, 13 others were killed.

May

• May 1
  • "The Paintings of Paul McCartney" exhibit opens at the Lyz Art Forum in Siegen, Germany. The exhibit features around 70 paintings by the former Beatle.
  • Musical group Atari Teenage Riot starts a riot in Berlin with their anti-consumer and anti-government lyrics.^{[citation needed]}
• May 18
  • The Backstreet Boys release their third studio album Millennium both in the US and internationally.
• May 29 – The 44th Eurovision Song Contest, held at the International Convention Center in Jerusalem, is won by Swedish singer Charlotte Nilsson with the song "Take Me to Your Heaven".

June

• June 1
  • Peer-to-peer file sharing network Napster is launched.
  • Blink-182 release their third studio album Enema of the State, which debuted at #9 on the Billboard 200, skyrocketing the band into mainstream success and spearheading a second wave of pop-punk.
• June 2 – The Backstreet Boys smash the old first-week sales record of Garth Brooks' 1.08 million, with Millennium, which sold over 1.13 million in its first week and was the first album to sell over 500,000 copies at least 2 weeks. The album holds at No. 1 first-weeks sales record of the 1990s.
• June 13 – S Club 7 debut at #1 on the UK singles chart with their first single "Bring It All Back" and become the largest vocal group to enter at the top.
• June 22
  • Christina Aguilera releases "Genie in a Bottle", which becomes a worldwide hit, selling over seven million copies.
  • Limp Bizkit's second album, Significant Other, debuts at number one on the Billboard 200, with 643,874 copies sold in its first week. The album launches them into mainstream success.
• June 25
• June 25, 1999 was the 176th day of the year 1999, under the sign of Cancer & the day of the week was Friday.
• If You Had My Love by Jennifer Lopez
• June 28 – Britney Spears embarks on her first concert tour, ...Baby One More Time Tour. The tour only reached North America and garnered a positive review, but generated some controversy due to her racy outfit and accusation of lip syncing.
• June 29
  • Santana and Matchbox Twenty vocalist Rob Thomas release "Smooth", which peaks at #1 for 12 weeks.
  • Razor and Tie releases the single-disc version of Monster Ballads. It would eventually be certified platinum at the end of the year.

June 29, 1999; 25 years ago. Pokémon 2.B.A. Master is a 1999 album, the first soundtrack album released for the English localization of the Pokémon anime.

July

• July 1 – The new Scottish Parliament is formally opened with a rock concert in the shadow of Edinburgh Castle and is headlined by Garbage, whose lead singer Shirley Manson is at the time one of the biggest music stars from Scotland.
• July 3 – Indie rock icon Mark Sandman collapses on stage at the Giardini del Principe in Palestrina, Latium, Italy (near Rome) while performing with Morphine. He is soon pronounced dead of a heart attack at the age of 46. Morphine immediately disbands.
• July 8 – Adrian Erlandsson quits The Haunted as the drummer while the band hires Per Möller Jensen as Erlandsson's replacement.
• July 12 – Gregg Alexander issues a press release dissolving the New Radicals.
• July 13–18 – The third Yoyo A Go Go punk and indie rock festival opens in Olympia, Washington.
• July 20 – Powerman 5000 release their second studio album Tonight the Stars Revolt!
• July 22–25 – The highly anticipated Woodstock 99 festival takes place in Rome, New York. Performers include the Red Hot Chili Peppers, Korn, Kid Rock, Limp Bizkit, Rage Against the Machine, DMX, James Brown, and Jamiroquai.
• July 27 – Machine Head release their third studio album The Burning Red.

August

• August 14–15 – The Artist Formerly Known as Prince holds a weekend yard sale at his Paisley Park Studios, with part of the proceeds going to benefit underprivileged youth.^[4]
• August 24 – Christina Aguilera releases her self titled debut album. It will become one of the best selling albums of the year and sell over 14 million copies.
• August 27–29 – The third Terrastock festival is held in London.
• August 31 – Megadeth release eighth studio album Risk.

September

• September 1 – The Irish Music Hall of Fame opens; Van Morrison is the first inducted into the museum.
• September 9 – The MTV Video Music Awards of 1999 take place. Britney Spears has the most memorable performance of the event, performing her hit single "...Baby One More Time"; NSYNC joined her with their song "Tearin' Up My Heart".
• September 14 – Nu-Metal Band Dope Release their debut studio album Felons and Revolutionaries.
• September 17 – Rapper Eminem is sued by his mother for $10 million, claiming that public comments he made about her were slanderous and had caused emotional stress and financial harm.^[5] She eventually collects a mere $1,600 settlement in 2001.
• September 21 – David Bowie's twenty-first studio album Hours becomes the first complete album by a major artist legally available to download over the Internet, preceding the physical release by two weeks.^[6]
• September 30 – Billboard announces that Ministry of Sound Recordings Ltd is expanding into Australia after ending a partnership with MDS Dancenet and establishes Ministry of Sound Australia, known until 2005 as Ministry of Sound (UK) Pty Ltd. Ministry UK also secures a distribution deal with EMI Music Group Australasia Pty Ltd.^[7]

October

• October 9
  • "Heartbreaker", the lead single from Mariah Carey's seventh studio album, Rainbow, reaches #1 on the Billboard 100, becoming her 14th #1 single and also her 59th week atop the chart. When it stayed at #1 for a further week Carey surpassed The Beatles for the act with the most weeks spent at number one. The song also topped charts in Canada and New Zealand.
  • The first Coachella Valley Music and Arts Festival is held in California. The inaugural line-up consists of Beck, The Chemical Brothers, Tool, Morrissey and Rage Against the Machine.
  • The anti-poverty initiative NetAid is launched with simultaneous benefit concerts in London, New Jersey and Geneva.
• October 19 – 98 Degrees release their first Christmas album This Christmas.
• October 20 – Melissa Auf der Maur leaves Hole.

November

• November 5
  • Australian independent record label Liberation Music is formed.
  • Gary Cherone leaves Van Halen.
• November 11 – Toploader release their debut studio album, Onka's Big Moka.
• November 12 – 1970s rock star Gary Glitter is jailed for four months for downloading child pornography off the Internet.
• November 15 – Korn performs their entire album Issues at the Apollo Theater in New York City, becoming the first rock band ever to perform at the Apollo.
• November 16
  • Korn's fourth studio album, Issues, debuts at number 1 on the Billboard 200 with 575,000 copies sold in its first week.
  • Will Smith releases his second solo studio album Willennium.
• Released November 23–Michael W. Smith makes his nine album This Is Your Time.
• November 23 – University of Oregon student Jeffrey Levy, having downloaded MP3s without permission, is the first person ever convicted for copyright infringement under the NET Act of 1997. He is sentenced to two years of probation and a limit on Internet access.^[8]

December

• December 4 – The Spice Girls start their Christmas Tour around the UK, dubbed as the Christmas in Spiceworld Tour.
• December 14
  • BMI announces the most played songs on American radio and television in the 20th century BMI Announces Top 100 Songs of the Century (full list)
  • Paul McCartney returns to The Cavern Club to play a special concert for 300 fans.
  • Boy George is injured by a 62-pound disco ball that falls from a concert venue's ceiling during a rehearsal, nearly killing him as it almost landed on his head.
• December 27 – Puff Daddy and fellow rapper Shyne are arrested for weapons violations and other charges after a shooting in a Manhattan nightclub that leaves three people injured.
• December 30 – George Harrison survives a knife attack by an intruder in his Friar Park home.^[9]
• December 31 – Many special New Year's Eve concerts are held around the world to celebrate the arrival of the year 2000. Big shows include Barbra Streisand at The MGM Grand Las Vegas, The Eagles at the Staples Center in Los Angeles, Billy Joel at Madison Square Garden, and Metallica with Kid Rock and Ted Nugent playing for 54,000 the Pontiac Silverdome. The biggest concert that night is by Phish, however, playing for 75,000 people at the Big Cypress Indian Reservation in Florida.^[10]

Unknown

• Vocalist Lawrence Mackrory quits Darkane. The band hires by Andreas Sydow as his replacement after.

January–March

April–June

July–September

October–December

Release date unknown

• Amalgamation – Trapt
• Ella in Budapest, Hungary – Ella Fitzgerald
• Face Down – Serial Joe
• In Stereo – Bomfunk MC's
• A Matter of Time – Hilltop Hoods
• Mi Día de la Independencia – Lynda Thomas
• Motor Driven Bimbo – Rockbitch
• My Fruit Psychobells...A Seed Combustible – maudlin of the Well
• Retrograss – John Hartford, David Grisman, & Mike Seeger
• Side Show Freaks – 40 Below Summer
• Simple Pleasure – Tindersticks

Other Chart hit singles

Other Notable singles