The singer wanted to create music that would fit the style and production of the film, set in the days of the Untouchables law enforcement, and sang the songs accordingly.

Roger Ebert from the Chicago Sun-Times praised the matte paintings, art direction and prosthetic makeup design, stating: "Dick Tracy is one of the most original and visionary fantasies I've seen on a screen".

She would be inclined to develop a soundtrack for Dick Tracy and the film studio would see this as a promotional opportunity before the release of their product, since Madonna was popular as a recording artist.

According to J. Randy Taraborrelli, author of Madonna: An Intimate Biography, by the 1980s record labels started to release albums which were closely associated with a film, thereby gaining double promotion.

[6] The songs on the album reflect Madonna's showgirl personality where her singing ranged from "rootsy, rocking" in nature to slow, "laid-back and soulful" vocals.

"[24] O'Brien said that the songs on I'm Breathless had a "coquettish" and "pandering nature", and was the polar opposite to Madonna's previous release, Like a Prayer, which had an introspective composition.

[24] I'm Breathless opens with the sound of an intercom and a shuffle, and power ballad "He's a Man" starts, a song which Madonna sings as if she was a "hooker stalking the boulevard".

[25] According to Rooksby, "the chorus bursts into life, with Madonna clearly relishing the lyrics about good guys finishing last... the coldness of her delivery is apt for the topic."

[30] The word "Dick" is continuously repeated in the main melody structure until the song ends with the sound of a record being snatched off a music player.

The song also has a rap section, where Madonna names various "golden era" Hollywood celebrities, including Greta Garbo, Marilyn Monroe and Marlene Dietrich.

Madonna's performance recreated the royal court of Marie Antoinette, dripping with sexual innuendo; at one point the singer flipped open her large skirt, allowing one of the dancers to crawl inside.

Consisting of 57 dates, the concert was divided into five sections, the first inspired by the 1927 German expressionist film Metropolis, the second by religious themes, the third by Dick Tracy and cabaret, the fourth by Art Deco, and the fifth was an encore.

The concert was criticized for its sexual content and religious imagery; in Toronto, Canada, Madonna was threatened of being arrested for obscenity,[42] and Pope John Paul II later called for a boycott, with one of the three Italian dates being cancelled.

[43] The performance of the I'm Breathless songs began with "Sooner or Later" sung atop a grand piano, followed by "Hanky Panky", with Madonna standing in front of a microphone.

[52] "Vogue" has been continuously acclaimed since its release; reviewers have praised its anthemic nature, calling it a "funky" and "catchy" song, and listed it as one of the singer's musical highlights.

[53] The music video for "Vogue", directed by David Fincher, showed Madonna paying homage to various golden era Hollywood actresses.

[54] Critics noted the way in which Madonna used her postmodern influence to expose an underground subcultural movement to the masses and for making the sex and gender roles ambiguous in its portrayal of people.

[74] Lucky Lara from Manila Standard Today denoted the album as a "surprise career decision" for Madonna and found that it showcased the singer's versatility and other facets of her pop personality.

[75] Writing for the Sarasota Herald-Tribune, Liz Smith gave another positive review, calling the album "excellent, different from anything [Madonna] has ever attempted", and listing the Sondheim songs as highlights.

[76] Ray Boren from Deseret News was impressed with Madonna's vocals, calling them "sultry" and "cutesy", listing "Vogue" and "Something to Remember" as highlights.

[77] Greg Sandow of Entertainment Weekly gave I'm Breathless an A rating, praising Madonna for "invent[ing] a new Broadway vocal persona, built around a chest voice not yet perfectly under control but still much richer and duskier than her low range sounded before.

[72] Mark Coleman from Rolling Stone gave the album a rating of three-and-a-half out of five stars and positive review, claiming that Madonna "pulls it off with brass and panache".

"[78] Dave Tianen from Milwaukee Journal Sentinel described the album as a "mixed bag of period pieces, some of them too cute for their own good", adding that "I'm Breathless never becomes more than the sum of its mannerisms".

[79] AllMusic critic Stephen Thomas Erlewine claimed that the songs are just "cutesy novelty numbers", and listing "Vogue" as a standout track.

[26] Mark Cooper from Q magazine lamented, in its June 1990 review, "It's something of a disappointment because the lady herself stays so firmly committed to a character who's less original than the persona she evolved during the '80s.

[1] While reviewing the album on its 30th anniversary, Mike Wass from Idolator wrote that its "genius" lied in the ability to "find the middle ground between Broadway fare and top 40 pop", concluding that "[Madonna] wasn't trying to bend and twist into another genre, she simply dismantled it and took the bits and pieces that pleased her".

[81] Rolling Stone's Joe Blistein deemed it one Madonna's most "fascinating" albums; "she could have easily recorded the three Sondheim songs for Dick Tracy and called it a day.

He did finish his review by expressing: "[I'm Breathless] remains a compelling snapshot of a pivotal moment in Madonna's life and career, when the world rolled in ecstasy at her feet and she had the power to push it any which way she wanted, to mold it to suit her ideal".

[105] In his article titled, "Madonna puts '30s in vogue", music critic Jon Pareles described that the record represented the tie-in as triple play, with the album, tour, and film promoting "one another".

[112] Others discussed how Madonna would introduce Stephen Sondheim to a newer audience in her generation, including Elizabeth Wurtzel from New York and Rolling Stone's Mark Coleman.