Happy 30th Anniversary to Madonna’s I’m Breathless: Music from and Inspired by the Film ‘Dick Tracy’ originally released May 22, 1990.

1990 was most definitely a defining year in Madonna’s career. In fact, it may just be her most definitive. Fresh out of the career resplendent ‘80s and hot off the heels of the success of Like A Prayer (1989), Madonna entered 1990 with a massive bang by releasing “Vogue,” a song that remains synonymous with the singer until this very day. Paying homage to ballroom culture and with thumping house beats, “Vogue” was the epitome of what a classic dance track should and could be.

After the release of “Vogue” and its incomparable success, Madonna embarked on the now infamous Blonde Ambition Tour causing controversy wherever she went. The show had a heady focus on Religion, her Like A Prayer album and of course “Vogue,” but it also included three songs from her then upcoming film, Dick Tracy. Honoring her character, night club singer Breathless Mahoney, she wore a green showgirl outfit as she sang “Sooner Or Later,” “Hanky Panky” and “Now I’m Following You.” Both the stage and choreography were inspired by the classic movie performances of Fred Astaire and Ginger Rogers and were an interesting departure from the rest of the show.

Given the high profile Madonna had at the time, coupled with the controversy surrounding her on stage performance of “Like A Virgin,” it not only seemed like a logical extension to hock her latest film and accompanying album, but it was also an incredibly smart business move. Dick Tracy was set in the 1930s and Madonna—who at the time had a hyper-sexualized, religious angst-riddled persona—seemed to be the furthest thing from the somewhat brassy, but gentle character of night club singer Breathless Mahoney. Whilst the film adaption of Mahoney was different from the original comic strip, Madonna again managed the unimaginable and brought not only a new dimension to Mahoney, but essentially also brought the character to life.

It’s true that I’m Breathless is a collection of big band pop songs that make up a film soundtrack, but more than this, the album finds Madonna taking on music by the legendary Stephen Sondheim. Sondheim, who is arguably one of the most important figures in musical theatre, contributed three tracks to the album; the sultry “Sooner Or Later,” the jazzy “More” and the beautiful duet with Mandy Patinkin, “What Can You Lose.” Madonna took to these songs like a duck to water and showed that pop was not her only repertoire. Her singing is given great range and she not only tackles genres like Jazz and Big Band, but conquers them with great aplomb.

As per usual, Madonna had an immense amount of input on the album, co-writing six of the album’s twelve songs and co-producing every track. Joined by (then) long time collaborators Patrick Leonard and Shep Pettibone, Madonna also managed to bring a playful vibe to the album. The seductiveness of the album opener “He’s A Man” also has a devilish element that allows for songs like “Hanky Panky,” a cheeky double entendre, to breathe life amongst its peers.

“I’m Going Bananas” provides a fun, lighthearted, almost Carmen Miranda-like energy with its latin flavored sound. The impassioned “Something To Remember” played to a conversation on self-love, a topic that Madonna would go on to explore more later in her career. Never one to sit in the “comfort zone,” as the album draws to a close, Madonna and then boyfriend and co-star Warren Beatty duet on the two-part “Now I’m Following You.” Part one continues the album’s big band theme before segueing into a ‘90s dance track for part two. Complete with background tap dancers, Madonna breathily quoting Socrates (“An unexamined life is not worth living”), another double entendre with Tracy’s first name (Dick) and a line from “Hanky Panky” (“My bottom just hurts thinking about it”) being morphed into a sexual mashup, Madonna again manages to get her exposition to the forefront.