1998

• Jan (7) Madonna begins filming "Frozen" video in the Mojave Desert, CA, directed by Chris Cunningham.
• (13) Madonna is #3 on Mr. Blackwell's 38th annual list of the worst-dressed women of 1997.
• (18) Madonna presents the award for Best Actor In A Motion Picture, Musical Or Comedy to Jack Nicholson in As Good As It Gets at the 55th annual Golden Globe Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
• Feb (14) Madonna performs a surprise mini-concert at 2:00 am to a sold-out crowd of 2,500 at The Roxy Club, New York, NY to promote her new CD Ray Of Light - it is her first club performance in 14 years.
• (16) "Frozen" video premieres on MTV.
• (17) Madonna arrives in London, England to begin her European promotional tour for Ray Of Light.
• (21) Madonna performs "Frozen" on BBC1-TV's National Lottery Show in London, England.
• (24) Madonna performs "Frozen" at the San Remo Song Festival in San Remo, Italy.
• (27) Madonna performs "Frozen" and is interviewed on TF1's Les Années Tubes TV show in Paris, France.
• (28) Madonna performs "Frozen" on Wetten Dass TV show in Duisberg, Germany.
• Mar (1) Inside Madonna TV special premieres on MTV.
• (2) Madonna completes her European promotional tour for Ray Of Light in Madrid, Spain.
• (3) Ray Of Light CD and "Frozen" single are released.
• (6) Madonna visits Toronto, ON, Canada to promote Ray Of Light: she attends a press conference at The Sutton Place Hotel and is interviewed live at 6:00 pm on MuchMusic TV.
• (10) "Don't Cry For Me Argentina" wins Favorite Song From A Movie (Evita) at the 4th annual Blockbuster Entertainment Awards at the Pantages Theatre, Los Angeles, CA.
• (13) Madonna guests and performs "Frozen" on NBC-TV's The Rosie O'Donnell Show.
• (15) Madonna attends the New York premiere of film Wide Awake (starring Rosie O'Donnell) at the Ziegfeld Theatre.
• (21) Ray Of Light hits US #2.
• (23) Madonna presents the Oscar for Best Original Song to James Horner and Will Jennings for "My Heart Will Go On" from Titanic at the 70th annual Academy Awards at the Shrine Auditorium, Los Angeles, CA.
• (24) Evita is released on DVD.
• (25) Madonna begins filming "Ray Of Light" video in Los Angeles, CA and New York, NY, directed by Jonas Akerlund.
• Apr (1) Madonna attends the premiere of film Mercury Rising in Beverly Hills, CA.
• (4) Madonna presents the Kids' Choice Blimp Award for favorite movie to Titanic and introduces a live performance by Cleopatra at the 11th annual Nickelodeon's Kids' Choice Awards at the UCLA Pauley Pavilion, Los Angeles, CA. "Frozen" hits US #2.
• (12) Madonna Rising TV special premieres on VH1.
• (22) Madonna attends the New York premiere party of film Two Girls And A Guy at the club Moomba. Ray Of Light is certified 2x platinum (2 million units).
• (27) Madonna performs "Frozen" with the East Harlem Violin Project at the 9th annual Rainforest Foundation Benefit Concert at Carnegie Hall, New York, NY, and also joins Elton John, Sting, James Taylor, Billy Joel, Herbie Hancock, Roberta Flack, Emmylou Harris and Joe Cocker in a rendition of The Beatles' "With A Little Help From My Friends" and "Twist & Shout".
• (28) Madonna attends the New York premiere of film Artemisia.
• (30) "Frozen" single is certified gold (500,000 units).
• May (8) Madonna is signed to co-star with Rupert Everett in Paramount Pictures film The Next Best Thing.
• (12) "Ray Of Light" video premieres on MTV.
• (18) "Don't Cry For Me Argentina" is honored as one of the Most Performed Songs Of 1997 at the 15th annual ASCAP Pop Music Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
• (21) Like A Virgin is certified 10x platinum (10 million units).
• (29) Madonna guests on CBS-TV's The Oprah Winfrey Show: she performs "Ray Of Light" and "Little Star".
• Jun (23) "Ray Of Light" single and video single are released.
• (25) Madonna begins filming "Drowned World/Substitute For Love" video in London, England, directed by Walter Stern.
• (30) Madonna - BIOrhythm TV special premieres on MTV.
• Jul (1) Madonna and Lourdes attend a Spice Girls concert at Madison Square Garden, New York, NY.
• (7) Madonna is the centre of a controversy when The London Daily Mirror accuses her of exploiting the late Princess Diana's tragic death in "Drowned World/Substitute For Love" video; a spokeswoman for Madonna releases a statement explaining that the video has nothing to do with Princess Diana and her life or her death.
• (11) "Ray Of Light" hits US #5. "Ray Of Light" video single hits US #4 on Top Music Videos chart.
• (25) "Drowned World/Substitute For Love" video premieres in Europe. "Ray Of Light" wins Video Of The Year at the 1998 VH1 Viewer's Vote Awards.
• Aug (1) Madonna is named VH1's Artist Of The Month.
• (8) Madonna begins filming "The Power Of Good-Bye" video in Los Angeles, CA, directed by Matthew Rolston.
• (12) Madonna is interviewed on ABC TV's Entertainment Tonight.
• (14) Madonna wins Best International Act at the German VIVA Comet Media Awards at the Akropolis in Cologne, Germany.
• (16) Madonna celebrates her 40th birthday. Madonna: Behind The Music documentary premieres on VH1.
• (24) "Drowned World/Substitute For Love" is released as a UK single.
• (25) Madonna reads the poem "Bittersweet" on Deepak Chopra's 2-CD set A Gift Of Love - Deepak & Friends Present Music Inspired By The Love Poems Of Rumi.
• (31) Madonna is interviewed on the set of "The Power Of Good-Bye" video on ABC-TV's Entertainment Tonight.
• Sep (5) "Drowned World/Substitute For Love" hits UK #10.
• (10) Madonna performs "Shanti/Ashtangi" and "Ray Of Light" at the 15th annual MTV Video Music Awards at the Universal Amphitheatre, Los Angeles, CA; "Ray Of Light" wins Best Video, Best Female Video, Best Direction, Best Choreography, Best Editing and "Frozen" wins Best Special Effects. "Ray Of Light" single is certified gold (500,000 units).
• (9,10) Madonna is featured in a 2-part interview on ABC-TV's Good Morning America.
• (11) "The Power Of Good-Bye" video premieres on MTV.
• (16) The World Vaishnava Association (WVA) condemns Madonna's performance of "Shanti/Ashtangi" at the MTV Video Music Awards on Sept 10 as sacrilegious in which she wore a holy facial marking and a see-through blouse. The New York Post announces that Madonna is dating 29-year-old British film director Guy Ritchie.
• (17) Madonna releases a statement against the WVA's criticism of her MTV performance: "The essence of purity and divinity is non-judgement… they should practice what they preach… if they're so pure, why are they watching MTV?"
• (24) Madonna accepts the Best International Video award for "Ray Of Light" via taped message at the 9th annual MuchMusic Video Awards at the Chumcity Building, Toronto, ON, Canada.
• (27) Madonna is guest of honor at the 14th annual AIDS Walk Los Angeles at Paramount Studios, Hollywood, CA.
• (28) Madonna narrates a chapter of "The Emperor's New Clothes" story on the Starbright Foundation benefit CD The Emperor's New Clothes: An All-Star Retelling Of The Classic Fairy Tale.
• (29) "The Power Of Good-Bye" single is released.
• Oct (15) Madonna is featured in book Ladies Home Journal's 100 Most Important Women Of The 21st Century.
• (21) Madonna presents the Man Of The Year Award to Sting at GQ's Men Of The Year Awards at Radio City Music Hall, New York.
• (22) "Borderline", "Papa Don't Preach", "True Blue" and "You Must Love Me" singles are certified gold (500,000 units).
• (23) Madonna performs "The Power Of Good-Bye" at the 4th annual VH1 Fashion Awards at the Theatre in Madison Square Garden, New York, NY; she is honored with the Gianni Versace Tribute Award and wins Most Fashionable Artist.
• (30) Madonna begins a European promotional tour for "The Power Of Good-Bye" single.
• Nov (1) Madonna makes a surprise appearance in London, England to present a lifetime achievement award to film director Alan Parker (Evita) at the Directors' Guild of Great Britain dinner in his honor on a boat on the River Thames.
• (7) Madonna performs "The Power Of Good-Bye" on Wetten Dass TV show in Linz, Austria.
• (9) Madonna is interviewed on NRJ Radio Show in Paris, France.
• (10) Madonna performs "The Power Of Good-Bye" and "Drowned World" on TF1's Les Années Tubes TV show in Paris, France.
• (12) Madonna performs "The Power Of Good-Bye" at the 5th annual MTV Europe Music Awards at the Fila Forum in Milan, Italy and wins 2 awards: Best Female and Best Album (Ray Of Light).
• (14) Madonna attends a press conference at the Grand Hotel in Stockholm, Sweden - her first visit to Sweden in 8 years.
• (15) Madonna performs "The Power Of Good-Bye" and is interviewed on Luuk TV show in Stockholm, Sweden.
• (17) Madonna performs "The Power Of Good-Bye" and "Drowned World" on El Septimo De Caballeria TV show in Madrid, Spain.
• (19) Madonna performs "The Power Of Good-Bye" on BBC1-TV's Top Of The Pops in London, England.
• (20) Madonna is interviewed by Johnny Vaughan on his BBC-TV show in London, England.
• (28) "The Power Of Good-Bye" hits US #11.
• Dec (6) Madonna narrates "The Camel Dances" story on animated HBO-TV special Rosie O'Donnell's Kids Are Punny.
• (7) Madonna congratulates Tony Bennett on his 50th anniversary in show business via taped message during his A&E-TV special Tony Bennett - Live By Request: An All-Star Tribute.
• (9) Madonna attends the 9th annual Fire & Ice Ball at Universal Studios, Los Angeles, CA.
• (11) Ray Of Light is certified 3x platinum (3 million units).
• (26) Madonna wins 2 Billboard Music Awards: Top Dance Club Play Artist and Top Dance Club Play Single ("Ray Of Light").
• (30) In Denmark, Madonna and Ray Of Light are named the most popular artist and album of 1998.

1999

• Jan (1) Madonna is voted Artist Of The Year by readers of the music internet website Rock On The Net.
• (4) Ray Of Light is voted Favorite Album Of The Year by Billboard magazine.
• (5) Madonna and Ray Of Light are nominated for 6 Grammy Awards: Album Of The Year, Record Of The Year, Best Pop Album, Best Dance Recording, Best Recording Package and Best Short-Form Music Video.
• (9) Madonna begins filming "Nothing Really Matters" video in New York, NY, directed by Johan Renck.
• (12) Madonna is #2 on Mr. Blackwell's 39th annual list of the worst-dressed women of 1998.
• (18) Madonna guests on CNN-TV's Larry King Live.
• (21) Madonna wins Best Female Artist and Best Dance/Electronica Artist in Rolling Stone magazine's 23rd annual Readers Poll.
• (29) Ray Of Light is voted Pop/Rock Album Of The Year by Playboy magazine.
• Feb (2) Madonna signs a long-term licensing and marketing contract with Sony Signatures: she will lend her name and image to fashion designers and manufacturers of fragrances, cosmetics and collectibles, and Swiss watchmaker Ebel.
• (5) Madonna is interviewed on ABC-TV's Entertainment Tonight.
• (6) Madonna wins Best International Female Artist and Best International Album (Ray Of Light) at the 10th annual Dansk Grammy Awards at Tivoli's Garden Concert Hall in Copenhagen, Denmark.
• (8) Madonna wins Female Artist Of The Year at the 1st annual NRJ Radio Awards at Cirkus in Stockholm, Sweden.
• (10) Madonna attends a reception at Astra in the D&D Building, New York, for the unveiling of Esquire magazine's March 1999 issue about the AIDS crisis in which she is featured on the cover with other AIDS activists.
• (13) "Nothing Really Matters" video premieres on MTV.
• (16) Madonna attends the Los Angeles premiere of Guy Ritchie film Lock, Stock And Two Smoking Barrels.
• (22) Max Factor announces a $6.5 million agreement with Madonna to collaborate on a line of several new cosmetic products, and she will also appear in TV commercials and ad campaigns which will run in Europe, Japan and Asia.
• (24) Madonna performs "Nothing Really Matters" at the 41st annual Grammy Awards at the Shrine Auditorium, Los Angeles, CA; Ray Of Light wins Best Pop Album, Best Dance Recording, Best Recording Package and Best Short-Form Music Video.
• Mar (2) Maverick Recording Company and Warner Bros. Inc. announce a long-term extension of their joint venture which also includes a new long-term contract with Maverick partners Madonna, Guy Oseary and Ronnie Dashev.
• (3) Madonna is voted Electronic Artist Of The Year and Ray Of Light is voted Electronic Album Of The Year in the 2nd annual Sonicnet / Addicted To Noise Readers Poll.
• (4) Madonna wins Best International Female Artist at the 39th annual Edison Music Awards in Amsterdam, Holland.
• (9) "Madonna - Ciao Italia: Live From Italy" (1988) is released on DVD.
• (15) Madonna is named one of People magazine's "25 Legends Of The Past 25 Years".
• (17) Madonna wins Best Dance Artist - Solo and Best Dance Video ("Ray Of Light") at the 14th annual International Dance Music Awards at the Winter Music Conference in Miami, FL.
• (19) Madonna attends Sony Music's pre-Academy Awards party at Mondrian Hotel's Asia de Cuba restaurant, Los Angeles, CA.
• (20) Madonna begins filming Max Factor commercial in Los Angeles, CA, directed by Alek Keshishian.
• (21) Madonna attends the Vanity Fair post-Academy Awards party at Morton's restaurant, West Hollywood, CA.
• (29) Evita: The Complete Motion Picture Music Soundtrack is certified 5x platinum (5 million units).
• Apr (5) Madonna is voted the Most Positive & Influential Sexual Voice Of The Past 35 Years in a USA Today online survey.
• (9) "Ray Of Light" wins Pop Video Of The Year and "Frozen" wins Best Special Effects In A Music Video at the 8th annual Music Video Production Association (MVPA) Awards at the Egyptian Theatre, Los Angeles, CA.
• (13) "Nothing Really Matters" single is released.
• (14) Ray Of Light wins Best Foreign Album Of The Year at the Fryderyk Music Awards in Warsaw, Poland.
• (20) Four Rooms (1995) is released on DVD.
• (23) Madonna begins filming The Next Best Thing, starring Rupert Everett and Benjamin Bratt, directed by John Schlesinger.
• (25) Madonna is featured in various photographs in The UK Sunday Times for the Max Factor campaign.
• (30) The Max Factor commercial premieres on TV in Europe.
• May (1) Madonna begins filming "Beautiful Stranger" video at Universal Studios, Los Angeles, CA, directed by Brett Ratner.
• (2) Madonna wins Best International Pop/Rock Album (Ray Of Light) and Best International Music Video ("Frozen") at the 6th annual Croatian Porin Music Awards in Makarska, Croatia.
• (8) "Nothing Really Matters" hits US #93.
• (11) Madonna & Ricky Martin duet "Cuidado Con Mi Corazon (Be Careful With My Heart)" is featured on his CD Ricky Martin.
• (13) Ray Of Light is named one of Rolling Stone magazine's "Essential Recordings Of The 90s".
• (17) "Frozen" is honored as one of the Most Performed Songs Of 1998 at the 16th annual ASCAP Pop Music Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
• (19) "Beautiful Stranger" video premieres on MTV. Madonna is interviewed by Charlie Rose on CBS-TV's 60 Minutes II.
• (23) Guinness Book of Records - Top 100 Singles includes "Crazy For You" #16 and "Holiday" #33.
• (26) "Ray Of Light" is honored as Top ASCAP Dance Song at the 12th annual ASCAP Rhythm & Soul Music Awards in the Hammerstein Ballroom at Manhattan Center, New York, NY.
• Jun (1) "Beautiful Stranger" single (from film Austin Powers: The Spy Who Shagged Me) is released.
• (8) "The Immaculate Collection" (1990) is released on DVD.
• (10) Madonna and Rupert Everett attend the Los Angeles premiere of his film An Ideal Husband.
• (16) Madonna is interviewed on ABC-TV's Entertainment Tonight.
• (29) Madonna files a $2.5 million lawsuit against her ex-financial advisors, Padell, Nadell, Fine, Weinberger & Co. for malpractice and breach of contract: she claims to have paid $2 million in New York state income taxes in 1992 after the firm prepared her taxes saying she was a California resident; Madonna seeks $2 million in compensatory damages and $500,000 in punitive damages.
• (30) Madonna completes filming The Next Best Thing in Los Angeles, CA.
• Jul (15) "Beautiful Stranger" is the most-played song on radio ever in UK: it was played 2,462 times in only one week.
• (17) During a 2-week vacation in Europe, Madonna attends the Versace Fashion Couture party at Man Ray Club in Paris, France.
• (24) "Beautiful Stranger" hits US #19.
• (26) "Beautiful Stranger" wins Best Pop Song Of The Year on BBC2-TV's Gaytime TV Awards in London, England.
• Aug (2) Madonna attends the Talk magazine launch party on Liberty Island, Manhattan, NY.
• Sep (9) Madonna wins Best Video From A Film for "Beautiful Stranger" and co-presents with Paul McCartney the Best Video Of The Year award to Lauryn Hill for "Doo Wop (That Thing)" at the 16th annual MTV Video Music Awards at the Metropolitan Opera House, New York, NY. (Madonna is crowned Most Honored Artist Of The 20th Century in the 15-year history of the MTV Video Music Awards with a career total of 18 awards).
• (12) Madonna and Lourdes attend the Versace Spring 2000 Show at the Roseland Ballroom, New York, NY.
• (30) "Blond Ambition Tour" is named The Greatest Concert Of The 1990s by Rolling Stone magazine.
• Oct (7) Madonna wins Favorite Female Artist at the 1st annual ARTIST Direct Online Music Awards in Los Angeles, CA.
• (13) Madonna attends the Details magazine party at the Metropolitan Pavilion, New York, NY.
• (17) Madonna receives death threats from a telephone caller on her way to London, England to begin work on a new album; upon their arrival at Heathrow Airport, Madonna and Lourdes are escorted by police but there are no incidents.
• Nov (1) Guinness World Records: Madonna is the most successful female solo artist for selling 120 million albums worldwide.
• (7) Madonna is #5 on "Top Entertainers Of The Half-Century (1950-2000)" list by Entertainment Weekly magazine.
• (9) "Madonna: The Video Collection 1993-99" is released on home video and DVD. Madonna is named Top-Selling Female Rock Artist Of The Century by the Recording Industry Association Of America (RIAA).
• (13) In UK, Madonna is voted Female Performer Of The Millenium on Channel 4's Music Of The Millenium Poll.
• (17) Madonna is voted Favorite Female Music Artist Of The 80s (37.8% votes) on AccessHollywood.com - Millenium Poll.
• (27) "Madonna: The Video Collection 1993-99" hits US #3 on Top Music Videos chart.
• (30) MTV & TV Guide's Top 100 Videos Ever Made includes "Vogue" #2, "Express Yourself" #10 and "Lucky Star" #50.
• Dec (1) Madonna is crowned Artist Of The Millenium by MTV Asia. Madonna is voted #3 Artist Of The Decade and "Beautiful Stranger" is #2 Song Of The Decade in RollingStone.com and TDK's "90s Music Time Capsule" Online Survey.
• (5) Madonna presents the Male Celebrity Style Award to Rupert Everett at the 5th annual VH1/Vogue Fashion Awards at the Lexington Avenue Armory, Manhattan, NY.
• (12) Madonna is #8 on The Detroit Free Press newspaper's "100 Greatest Artists & Entertainers Of Michigan's Century".
• (14) Madonna is voted Female Artist Of The Century by readers of SongLink International, a UK songwriters and music magazine.
• (18) Madonna is #3 on VH1-UK's "Millenium Honors List" of the top 100 greatest artists of the millenium.
• (25) Madonna is featured in Billboard magazine's "Totally 90s - Diary Of A Decade": Top Pop Artist Of The Decade #6, Top Pop Female Artist Of The Decade #4, Hot 100 Singles Of The Decade "Take A Bow" #24 and "Vogue" #93.
• (28) Madonna is honored as Female Artist Of The Millenium by Radio Tel Aviv in Israel.
• (30) In Australia, Madonna is voted #1 "Female Music Star Of The Millenium" in a Virtual Time Capsule by 2DayFM radio station.
• (31) MuchMusic: Top 100 Videos Of The Century includes "Express Yourself" #3, "Ray Of Light" #8 and "Like A Prayer" #47.

Read more of Madonna's Career Diary...