For this album, Madonna goes back in time to a completely different musical age - the 1940's, when pop music was very different, although the 1940's style is obscured somewhat by a 1990's production style. This is a light-hearted album, more in keeping with (though very different from) the song-and-dance music that Betty Grable did than the pop music of Dinah Shore or Jo Stafford. Some songs are covers of songs from that period but most are original songs written in style of the time, even including some novelty songs that you either love or hate. Madonna's big hit of the time, Vogue, was added to the album to help sales but it doesn't really blend in.
Stephen Sondheim composed three of the songs, these being Sooner or later, More and What can you lose - a duet with Mandy Patinkin. Madonna's performances on these songs are impressive. Of Madonna's own songs, Hanky panky and Vogue were huge hits but the outstanding song is Something to remember, which later became the title track of a compilation of her ballads. He's a man and Back in business are also wonderful. I also enjoyed Cry baby but I can imagine that some people will not like this at all. Madonna did not write the two other original songs - I'm going bananas (a slightly sill but entertaining novelty song) and Now I'm following you parts 1 and 2 (a lot of fun but definitely not a novelty).
I had to play this album a few times before I really appreciated it, but I liked it more with each listen. Although this album is just for fun, Madonna's covers of the Sondheim songs suggest that she could record a serious jazz album if she ever wants to.
This is not like any of Madonna's other albums so some of her fans may not like it. At the same time, I'm not sure that it will win her any new fans. Nevertheless, this is a fascinating album that proves just how versatile Madonna really is.