- Jan 3 "Side Show," closes at Richard Rodgers NYC after 91 performances
- Jan 4 "Funny Thing Happened on the Way to the Forum" closes at St James NYC after 715 perform
- Jan 4 "Ivanov" closes at Vivian Beaumont Theater NYC after 51 performances
- Jan 4 "Triumph of Love" closes at Royale Theater NYC
- Jan 11 "Proposals" closes at Broadhurst Theater NYC after 76 performances
- Jan 13 "Patti LaBelle On Broadway" opens at St James Theater NYC
- Jan 18 "Ragtime" opens at Ford Theater NYC
- Jan 25 Musical "Grease" closes at Eugene O'Neill Theater NYC after 1,503 performance
- Jan 25 "Patti LaBelle On Broadway" closes at St James Theater NYC
Event of Interest
Jan 25 Spice Girl Victoria Beckham (Posh) and soccer player David Beckham get engaged
Victoria Beckham
David Beckham
- Jan 26 25th American Music Awards: Spice Girls & Babyface win
- Jan 29 "Capeman," opens at Marquis Theater NYC
- Jan 29 Singers Bobby Brown found guiilty of DWI in Fort Lauderdale, Florida
- Feb 1 "Street Corner Symphony" closes at Brooks Atkinson NYC after 79 performances
- Feb 12 "Freak" opens at Cort Theater NYC
Event of Interest
Feb 18 Andrea Bocelli makes his operatic debut as Rodolfo in "La bohème" at the Teatro Comunale in Cagliari
Andrea Bocelli
- Feb 22 "King & I" closes at Neil Simon Theater NYC after 781 performances
Knighthood
Feb 24 Elton John knighted by Queen Elizabeth II at Buckingham Palace in London
Elton John
Elizabeth II
- Feb 25 40th Grammy Awards: "Sunny Came Home" best song, Paula Cole best new artist
Music Awards
Feb 27 12th Soul Train Music Awards: Puff Daddy, Whitney Houston win
Puff Daddy
Whitney Houston
- Mar 12 "Sound of Music" opens at Martin Beck Theater NYC
Event of Interest
Mar 15 "Cabaret" opens at Club Expo Theater, NYC, starring Alan Cumming and Natasha Richardson
Natasha Richardson
- Mar 19 "Ah Wilderness!" opens at Vivian Beaumont theater
Music Awards
Apr 22 33rd Academy of Country Music Awards: Garth Brooks, Trisha Yearwood and George Strait win
Garth Brooks
Trisha Yearwood
- May 9 43rd Eurovision Song Contest: Dana International for Israel wins singing "Diva" in Birmingham
Event of Interest
Jun 15 32nd Music City News Country Awards: Neal McCoy, Lorrie Morgan & Billy Ray Cyrus wins
Billy Ray Cyrus
- Jun 21 "Don't Be Cruel" 2nd studio album by Bobby Brown is released (Grammy Award Best Male R&B Vocal Performance 1990)
Music Single
Aug 3 Irish band Boyzone release their best-selling single "No Matter What" composed by Andrew Lloyd Webber and Jim Steinman
Album Release
Aug 25 "The Miseducation of Lauryn Hill" debut album by Lauryn Hill is released (5 Grammy Awards including Album of the Year, Billboard Album of the Year 1998)
Lauryn Hill
Video Music Awards
Sep 10 15th MTV Video Music Awards: Madonna & Will Smith win
Madonna
Will Smith
- Sep 23 32nd Country Music Association Award: Garth Brooks, Trisha Yearwood & George Strait win
Music Single
Oct 23 Britney Spears releases her debut single "Baby One More Time"
Britney Spears
- Oct 31 American jam band Phish performs The Velvet Underground's "Rock and Roll" as a musical costume during a show at the Thomas & Mack Center at the University of Nevada in Paradise, Nevada
- Nov 3 "400 Degreez" 3rd studio album by Juvenile is released (Billboard no. 1 year end Top R&B/Hip Hop Albums 1999)
Event of Interest
Nov 17 Whitney Houston releases "My Love is Your Love"
Whitney Houston
#1 in the Charts
Nov 17 Mariah Carey releases "#1's"
Mariah Carey