On May 20, 1996, Madonna’s “Take A Bow” was honored as one of the Most Performed Songs Of 1995 at the 13th annual ASCAP Pop Music Awards at the Beverly Hilton Hotel, Beverly Hills, CA.
On May 19, 1990, Madonna’s single “Vogue” hit #1 on the Billboard Hot 100 in the USA.
“Vogue” reached number one in over 30 countries worldwide, becoming Madonna’s biggest hit at that time. It was also the best-selling single of 1990 with sales of more than two million, and has sold more than six million copies worldwide to date.
On May 17, 1991, “Madonna: Truth Or Dare” was released in 538 US movie theatres.
“Madonna: Truth or Dare” (renamed “In Bed with Madonna” outside of North America) chronicled the life of Madonna during her 1990 Blond Ambition World Tour. The film was well received by critics and was successful at the box office, at that point becoming the highest-grossing documentary of all time with a worldwide gross of $29,012,935.
On May 16, 1994, Madonna’s “I’ll Remember (Theme From With Honors)” became the number-one single in Canada. The song remained at the top of the Canadian singles chart for five weeks before finally being dislodged on June 20th by All-4-One’s hit, “I Swear”. Incidentally, it was the same song that blocked “I’ll Remember” from reaching the top spot on the Billboard Hot 100 in the U.S., where it spent four weeks in its peak position of number-two.
On May 14, 1993, the 1000th episode of The Arsenio Hall Show aired, featuring Madonna as the headline act.
The 1000th episode was an AIDS benefit concert and it was filmed at the Hollywood Bowl.
Madonna performed “Fever” as well as “The Lady Is A Tramp” with Anthony Keidis from the Red Hot Chilli Peppers.