On October 23 1993, Madonna’s Rain peaked at #7 on Billboard’s Hot Adult Contemporary chart in the USA. Rain is Madonna’s longest charting single on the Hot AC chart, spending 125-weeks on the chart. Her second longest charting Hot AC single is Take A Bow (with 35-weeks on the chart).
On October 22 2005, Madonna made a surprise appearance at the Roxy in New York, with her Confessions on a Dance Floor producer, Stuart Price.
Madonna got hold of a microphone and told the crowd:
“You know I have a long history with the Roxy so I only thought it appropriate that I come here to share my new album with you and dance. It all started here with 12 inches. Some girls have all the luck. Are you fucking ready? Ok, let’s go.”
A remix of her single Hung Up played as Madonna danced and pulled people up on stage to dance with her. After Hung Up, DJ Peter Rauhofer played a mix of I Love New York.
After about 15-20 minutes of dancing and singing along to music, Madonna left.
On October 21 1995, the music video for I Want You by Madonna with Massive Attack hit #11 on VH1’s weekly chart in the U.S.
The video for I Want You is somewhat of an anomaly in Madonna’s career. The song was initially intended to be a joint release to promote both Inner City Blues (a Marvin Gaye tribute album on Motown Records) and Madonna’s own Something To Remember ballads collection on Sire/Maverick. Naturally, a music video was commissioned to accompany the planned single.
Unfortunately, legal wranglings between the two record companies ensued when Motown insisted on releasing the tribute album ahead of Madonna’s album. Concerned that the move could negatively impact sales of Something To Remember, Madonna’s label apparently backed away from plans to fully promote I Want You.
Fortunately for fans, the song’s excellent music video, which had already been completed by director Earle Sebastian, was not shelved. It was serviced to video channels ahead of the release of both albums and received moderate support despite the song’s absence from radio.
The video quickly faded into obscurity, however, once Madonna’s You’ll See single and its accompanying video were given a full promotional push from her label less than a month later.
On October 20 1984, Madonna’s debut album, Madonna, hit #8 on the Billboard 200 albums chart in the USA. It took the album over a year to reach its peak (it debuted on the Billboard 200 at #190 on September 3 1983), and went on to sell 10-million copies worldwide (5-million in the USA).
The artwork for Madonna was shot by photographer Gary Heery. Heery had this to say about the shoot:
“Madonna arrived at my Broadway studio in New York with a small bag of clothes and jewellery, and no entourage. Then, in front of the camera she was explosive, like a great model, but with her own unique style. She came over the next day to see some prints and the proofs, and there was shot after shot to choose from. We agreed on every choice and whittled it down to the album cover images. I had no idea what I had just been a party to.”
On October 12 1991, Madonna and Freddy DeMann attended the wedding of entertainment attorney Allen Grubman and real estate broker Deborah Haimoff.
The wedding was held at the New York Public Library. Other guests included Robert De Niro, David Geffen and Mariah Carey.
On October 11 1993, Madonna opened the North American leg of The Girlie Show at the SkyDome in Toronto, Canada.
The original Toronto date was October 12 (Thanksgiving Day in Canada), but due to overwhelming demand, a second show was added on October 11.
Madonna performed for 50,880 fans during the two Toronto shows.
The above two ads are the original Toronto Star ads from my (Jay’s) personal collection. Because the newsprint is so old I had to pump up the contrast on my scans to make them more visible.
Here is the full itinerary for The Girlie Show:
September 25 – Wembley Stadium, London England
September 26 – Wembley Stadium, London England
September 28 – Bercy, Paris France
September 29 – Bercy, Paris France
October 01 – Bercy, Paris France
October 02 – Festhalle, Frankfurt Germany (cancelled)
October 05 – Park, Tel Aviv Israel
October 07 – Inonu Stadium, Istanbul Turkey
October 11 – Toronto Skydome, Toronto Canada
October 12 – Toronto Skydome, Toronto Canada
October 14 – Madison Square Garden, New York United States
October 15 – Madison Square Garden, New York United States
October 17 – Madison Square Garden, New York United States
October 19 – The Spectrum, Philadelphia United States
October 21 – The Palace, Michigan United States
October 23 – Olympic Stadium, Montreal Canada
October 26 – Juan Ramon Stadium, Bayamon Puerto Rico
October 30 – River Plate Stadium, Buenos Aires Argentina
October 31 – River Plate Stadium, Buenos Aires Argentina
November 03 – Estadio Do Morumbi, Sao Paulo Brazil
November 06 – Estadio Do Maracana, Rio De Janeiro Brazil
November 10 – Foro Sol (Sun Forum), Mexico City Mexico
November 12 – Foro Sol (Sun Forum), Mexico City Mexico
November 13 – Foro Sol (Sun Forum), Mexico City Mexico
November 19 – Cricket Ground, Sydney Australia
November 24 – Anz Stadium, Brisbane Australia
November 26 – Cricket Ground, Melbourne Australia
November 27 – Cricket Ground, Melbourne Australia
November 29 – Cricket Ground, Melbourne Australia
December 01 – Oval, Adelaide Australia
December 03 – Cricket Ground, Sydney Australia
December 04 – Cricket Ground, Sydney Australia
December 07 – Fukuoka Dome, Fukuoka Japan
December 08 – Fukuoka Dome, Fukuoka Japan
December 09 – Fukuoka Dome, Fukuoka Japan
December 13 – Tokyo Dome, Tokyo Japan
December 14 – Tokyo Dome, Tokyo Japan
December 16 – Tokyo Dome, Tokyo Japan
December 17 – Tokyo Dome, Tokyo Japan
December 19 – Tokyo Dome, Tokyo Japan
On October 10, 2025, the second pressing of Madonna’s Veronica Electronica companion EP for the Ray of Light album was released — expanded beyond its original vinyl-only run to include a CD edition for the first time ever.
Originally released July 25, 2025, Veronica Electronica first appeared on silver nugget metallic vinyl, exclusive to the original 2025 pressing. Conceived by Madonna in 1998 as a companion remix project under her “Veronica Electronica” alter ego, the long-rumoured collection finally emerged nearly three decades later, featuring newly edited versions of remixes by Peter Rauhofer, William Orbit, Sasha, BT, and Victor Calderone.
Following overwhelming fan demand, the EP returned on October 10 — re-pressed on ultra-clear vinyl in a silver-printed mylar jacket, and newly issued in Deluxe CD format for the first time.
Track List:
Today In Madonna History 