So why did Warner UK decided to randomly re-release Holiday in 1991? It was a slow Madonna year? Why Holiday and not something more recent like Keep It Together or something off I'm Breathless?
The promo campaign went well into 1991 and the Immaculate Collection remained near the top of the charts for a considerable portion of 1991.
The four singles from the album were basically:
Justify My Love
Crazy For You
Rescue Me
Holiday
I guess after the success of Crazy For You (at the time of release promo indicated it was chosen by fan poll as the UK’s favourite Madonna single) it was obvious she could re-release anything at that point and it would make top ten if not top five.
Im not sure why Holiday was chosen again, especially as it had been released twice before and had no video and the released version wasn’t even the remix from the album.
There were even plans to release Into The Groove again later in the year after Holiday. The Immaculate Collection went back up to #3 around that time (August).
The tour video of Holiday seemed to get some kind of promo in the US that year so maybe they were thinking of sticking to re-releasing songs she had done on the Blond Ambition Tour (which ruled out Lucky Star)?