On December 22 1985, John “Jellybean” Benitez’ Sidewalk Talk (featuring Madonna) debuted at #48 on the Billboard Hot Dance/Disco chart (not to be confused with the Hot Dance Music/Maxi-Single Sales chart). The hit dance single peaked at #1 on the Dance/Disco chart on February 2 1986.
Sidewalk Talk was written by Madonna, arranged by Jellybean and Stephen Bray and mixed by Jellybean.
On December 21 1985, Madonna was awarded seven Billboard Music Awards, reflecting her significant impact on the Billboard charts in the preceding year:
On December 20 2005, Madonna’s official website confirmed that Jamie King would direct the music video for Sorry, the second single from Confessions On A Dance Floor.
The video was conceived as a sequel to the album’s first single, Hung Up.
On December 19 1987, Madonna’s haunting ballad The Look Of Love peaked at number nine on the UK Singles Chart. The third and final Madonna single from the Who’s That Girl soundtrack, it was released only in select European countries and in Japan.
The Look Of Love was written, produced and recorded by Madonna and Patrick Leonard during the second of a three-day studio session, with the title track of the soundtrack being written and recorded on the first day. Additional musicians were brought in for overdubs and mixing was completed for both tracks by the end of the third day.
Despite being a set-list staple on the Who’s That Girl tour – the song’s limited release, moderate chart success, along with the fact that it has not been included in any of Madonna’s subsequent retrospective collections has led to it being largely forgotten, although fans frequently cite it as an underrated gem.
In a 1991 interview with ICON magazine, background vocalist Niki Haris expressed fond memories of performing the track with Madonna during the 1987 tour:
“My favorite song ever to perform with Madonna was a song called The Look Of Love from the Who’s That Girl Tour [Niki sings: Nowhere to run, nowhere to hide…]. That is one of the greatest songs and Madonna sings it really great. That’s my favorite song of all time as far as singing with her.”
The single reached number six in Ireland, number eight in the Netherlands and number ten in Belgium, while it peaked outside the top-ten in Germany, Switzerland, France and Japan.
On December 18 2001, the first of a two-part interview with Matt Lauer to promote GHV2 aired on the Today show in North America. The second part aired the following day.
Coming off a busy year for Madonna, her involvement in promoting the retrospective was limited, with this being her only television interview that tied in with its release.
On December 17 2019, Cyndi Lauper posted this message on Facebook about Tracy Young’s Grammy nomination for her remix of Madonna’s I Rise:
I’m so excited to hear that Tracy Young has been nominated for a Grammy! This is a BIG deal. Not only did she do a killer remix of “Shine” for me in 2002, but she has been breaking ground for women for years. I can’t wait to vote for her and I urge all Recording Academy / GRAMMYs voting members to join me.
Tracy’s nomination is for her remix of Madonna’s I Rise – a great song with a really powerful message. One of my faves off the Madame X album. Tracy’s nomination marks the FIRST time a female Producer/Remixer has EVER been nominated in the Best Remixed Recording category since its inception in 1998, despite Tracy being eligible in previous years. Tracy has had over 60 #1 Billboard Club Chart Hits. She also worked with Michelle Obama on her This Is For My Girls song. Tracy is a true pioneer and I hope this inspires future generations of female Producers/Remixers. We NEED more of ya! #SheIsTheMusic
On December 16 1989, Dear Jessie debuted at #9 on the UK Singles Chart.
The single would climb to its peak position of #5 on December 30th, where it remained for three weeks before beginning its descent.
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