After a controversy fueled period, Madonna's personal life had started to dominate over her musical career, "She knew it was time to make a change" as said by one anonymous member of her management team who claimed that she wanted to prove there was more to her than the constant media circus surrounding her. Described as a "love letter from Madonna to her fans and music lovers alike" the compilation seemed to notify her contemporaries of her musical talent with Madonna jokingly commenting "...And these are just my ballads".
During the development Madonna worked with such producers as Massive Attack and Richard Page, but her work on the two tracks, "You'll See" and "One More Chance," saw her work with a well-known producer, which was unusual for Madonna, David Foster.
The packaging included with the release showed Madonna looking "deliciously cosmopolitan" as she wore a tight-fit white cocktail attire, whilst the back cover artwork is predominantly more playful. The front cover artwork presented Madonna leaning against a wall with an expression of "romantic loss or absorption". Designed as the Madonna album which would appeal to a larger audience in contrast to her previous records, Bedtime Stories and Erotica, the booklet featured red roses inside and a golden yellow flower on the back cover.
The title of the of the album derives from the Madonna song of the same name, featured on Madonna's Dick Tracy soundtrack entitled I'm Breathless. This Patrick Leonard-produced track was listed as the album's title because it had received little attention at the time of the soundtrack release.