On September 11 1988, Madonna participated in the Sport Aid 88: The Race Against Time marathon in New York.
“We can make future generations look back on this decade, and remember us as the generation who began to shape a world in which children enjoy a future free from hunger and pain. Please join the Race Against Time and help CARE and Sport Aid make a difference in a hungry child’s life.” – Madonna
On July 1 1988, Madonna made a surprise unscheduled appearance on NBC-TV’s Late Night With David Letterman. Sandra Bernhard was David’s scheduled guest.
On June 27 1988, Madonna and Sean Penn attended the Mike Tyson vs. Mike Spinks fight at the Trump Plaza Hotel & Casino in Atlantic City, New Jersey.
On May 3 1988, David Mamet’s Speed-the-Plow premiered on Broadway at the Royale Theatre in a production by the Lincoln Center Theater, closing on Dec 31, 1988 after 279 performances. The original Broadway cast featured Joe Mantegna, Ron Silver and Madonna until August 30 1988, after which the production was recast with David Rasche, Bob Balaban and Felicity Huffman for the remainder of its run.
The play was nominated for a Tony Award for Best Play and Best Direction of a Play (Gregory Mosher). Silver won a Tony Award for Best Actor (Play).
It has since been produced countless times for regional and national theatre audiences worldwide.
On January 23 1988, Madonna’s You Can Dance remix album hit #14 (and peaked) on the Billboard 200 chart.
Here is Stephen Thomas Erlewine’s review (from AllMusic.com) of You Can Dance:
Released in 1987 as a stopgap, the remix album You Can Dance reworks material from Madonna’s first three albums. Actually, it keeps the spotlight on her first record, adding non-LP singles like “Into the Groove” for good measure, along with a bonus track of “Where’s the Party.” Since it’s a dance album, it doesn’t matter that “Holiday” and “Into the Groove” are here twice, once each in dub versions, because the essential grooves and music are quite different in each incarnation. It is true that some of this now sounds dated — these are quite clearly extended mixes from the mid-’80s — but that’s part of its charm, and it all holds together quite well. Not essential, but fun.
On January 12 1988, Possessive Love, a song written by Madonna, Patrick Leonard & Jai Winding and performed by Marilyn Martin was released as the lead single from Martin’s second album for Atlantic Records, This Is Serious. Martin is perhaps best known for her chart-topping duet with Phil Collins, Separate Lives. Though Possessive Love failed to make any chart impact, Madonna’s involvement in the song has kept it from being completely forgotten.
In an interview by Breathe Cast writer Timothy Yap, Martin was asked about the circumstances surrounding the song:
I met Pat Leonard when I began the search for a producer for my second album. He’s the one who approached Madonna with the idea of writing a song for me and she graciously agreed. Pat called me one day while he was working on her Like a Prayer album and asked if I would like to come and sing backgrounds [on Cherish]. Talk about an ‘Are you kidding?’ moment! That was the only time I met her. She was impressive to say the least. Very in charge. She absolutely knows her mind and insists on her music being true to her vision. She was very focused and a tad intimidating, but that’s not surprising given her amazing success over the years. I thought it was pretty cool that before agreeing to write Possessive Love for me to sing on my album she asked Pat Leonard if I was a nice person.”
Martin’s claim that the song was written specifically for her rather than being a leftover from one of Madonna’s album sessions is likely accurate, given the fact that Winding was never involved in songwriting sessions for any of Madonna’s albums. Winding’s involvement as a musician in the Who’s That Girl Tour suggests that the song may have been written at some point during the 1987 tour.
The sentiments expressed in Possessive Love appear to align with the issues Madonna was reportedly facing in her marriage to Sean Penn at the time, with reports of their initial separation dominating the tabloids in late 1987. Madonna would revisit and further elaborate on her marital woes on the Like A Prayer album track, Til Death Do Us Part, which was written later in 1988.
On January 9 1988, Spotlight peaked at #15 on Billboard’s Hot Crossover Singles chart in the U.S.
Despite not being released as a single commercially outside Japan and receiving no direct promotion in the U.S., Spotlight managed to garner enough airplay for an eight-week run on the Crossover chart. It also appeared on the Hot 100 Airplay chart for five weeks, peaking at #32 in February, 1988.
