Madonna’s “The Immaculate Collection”

Released: November 13, 1990

Genre: pop

Label: Sire • Warner Bros.

Producer: Madonna • Lenny Kravitz • Shep Pettibone • Reggie Lucas • John “Jellybean” Benitez • Nile Rodgers • Stephan Bray • Patrick Leonard

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Madonna doesn’t need an introduction. Madonna has become a powerful force in the music industry since her self titled debut album in 1983, and now is one of the greatest pop artists of all time. Madonna has dabbled in every music genre possible, and broke down many barriers so much that I have to give her that credit. Throughout her almost 50 year career, Madonna’s work has incorporated social, political, sexual and religious themes. Now I don’t go up for many white artists, but Madonna Louise Ciccone will always receive her flowers from me.

The Immaculate Collection pays homage to Madonna’s career up until that time, containing fifteen previous released singles in chronological order from 1983 to 1990, with two unreleased tracks at the end. The title of the greatest hits collection is a pun of the Immaculate Conception , a conception of the Virgin Mary without the stain of original sin. Released in the United States on November 13, 1990 by Sire Records, The Immaculate Collection has since sold over 30 million copies worldwide, making it not only the best-selling compilation album ever by a solo artist, but of the world’s best-selling albums of ALL TIME. The power of Madonna is real.

Ladies & Gentlemen, I present to you: Madonna’s The Immaculate Collection.

Holiday (from Madonna, 1983)


Written by Curtis Hudson • Lisa Stevens-Crowder

The album opens with 1983’s Holiday, which pays homage to the common desire to take a break from everyday life, and celebrating to the best of your abilities with the people in your life. Holiday became Madonna’s breakthrough record, peaking at 16 on the Billboard Hot 100.

Lucky Star (from Madonna)


Lucky Star has a special place in my heart. I love this song because it’s my best friend’s favorite Madonna song period.  One of the quintessential records of Madonna’s before her superstardom, Lucky Star is a song that captures the essence of 80s pop culture, from the lyrics using a double entendre of comparing a lover’s body to stars in the sky…to the catchy post-disco beat that Madonna’s fan base has loved for generations.

Released as the fourth single from her self-titled debut album, Lucky Star gave Madonna her first top-five hit on the Billboard Hot 100 (peaking at number 4). The music video became an instant success and had a huge impact on pop culture due to Madonna’s fashion and style, which influenced the younger generation at the time to emulate her style. Just iconic!

***Lucky Star was sampled by Carly Rae Jepsen for her 2017 single Cut to the Feeling.

Borderline (from Madonna)


Borderline is my favorite song from Madonna, and rightfully so! From a lyrical perspective, Borderline is about the singer expressing how she dislikes her boyfriend’s sexist ways. 

The music video to Borderline is known for its use of power as symbolism. Madonna is credited for breaking the taboo of interracial relationships with the music video, and is one of her career-making moments. Released as the fifth and final single from the album, Borderline gave Madonna a top ten hit on the Billboard Hot 100 and has since been certified Gold by the RIAA.

***Borderline has been covered by Jody Watley.

Like A Virgin (from Like A Virgin, 1984)


Written by Thomas Kelly • William Steinberg

Like a Virgin is a song where it can have various types of meanings for anyone: an ode to someone’s lover who makes the singer feel like a brand new person, actual virgins who can appreciate the song before their first sexual experience and someone who can relive their first time as well. The song was released as the lead single of the album of the same name. Like a Virgin became Madonna’s first number one hit on the Billboard Hot 100, and also gave her a top ten hit on the Billboard R&B charts, at number 9.

Material Girl (from Like A Virgin)


Written by Peter Brown • Robert Rans

Material Girl is yet another song that established Madonna as the icon she is today. With influences of new wave and post disco, Material Girl is lyrically about the singer preferring to only date men who offer her the materialistic lifestyle she desires. The music video alone is remarkable with Madonna paying homage to Marilyn Monroe’s performance of Diamonds Are a Girl’s Best Friend in the 1953 film Gentlemen Prefer Blondes. Material Girl also peaked at number 2 on the Billboard Hot 100.

***Material Girl was sampled for:

  • Sparkling Diamonds by Nicole Kidman
  • Yo P My D by Willie D

***Material Gworrlllllllll by Saucy Santana & Madonna contains elements of Material Girl.

Crazy for You (from Vision Quest soundtrack, 1985)


Written by John Bettis • Jon Lind

Recorded for the soundtrack to the 1985 film Vision Quest, Crazy for You is lyrically a record about the sexual desires and attraction two people are having for one another. The song became Madonna’s second number-one on the Billboard Hot 100, and gave her a Grammy nomination for Best Female Pop Vocal Performance.

Into the Groove (from Like a Virgin, 1985 reissue)


Written by Madonna • Stephen Bray

Into the Groove was recorded for the soundtrack for the 1985 Desperately Seeking Susan, and is a classic Madonna record for the dance floors! Into the Groove is lyrically about self-liberation and invitation for someone to join her on the dance floor and let yourself be free.. Into the Groove was released as a single in the UK on July 15, 1985, peaking at number 1 on the charts.

Live to Tell (from True Blue, 1986)


Written by Madonna • Patrick Leonard

Live to Tell was released as the lead single to her third studio album True Blue, and is one of her best and strongest ballads. From a lyrical perspective, the song touches on resilience in the face of hardship, trauma, deceit and mistrust. Live to Tell became Madonna’s third number-one on the Billboard Hot 100, and is often still praised to this day by critics in retrospective reviews.

***Live to Tell was sampled for:

  • ILLumninate by Ab-Soul featuring Kendrick Lamar

Papa Don’t Preach (from True Blue)


Written by Brian Elliott • Madonna

Papa Don’t Preach is one of the songs where Madonna pushed the envelope as an artist, and was ahead of her time. Lyrically, the song drew inspiration conversations Brian Elliott heard amongst teenage girls in Hollywood…and teenage pregnancy was one of the topics. Papa Don’t Preach was eventually birthed with a story where a teen confesses to her father that she is with child, and intends to keep it. Papa Don’t Preach peaked at on the Billboard Hot 100 chart, becoming Madonna’s fourth number-one hit.

Papa Don’t Preach was sampled for:

Open Your Heart (from True Blue)


Written by Madonna • Gardner Cole • Peter Rafelson

Open Your Heart was released as the fourth single from the True Blue album, and is one of Madonna’s best dance records. Originally conceived as a rock and roll song for Cyndi Lauper, Madonna was eventually offered the song and changed the title and some lyrics. From a lyrical perspective, Open Your Heart was about the singer’s determination to get a man to be more vulnerable with her and get to know her. Open Your Heart became Madonna’s fifth number one single on the Billboard Hot 100, became the second female artist behind Whitney Houston to obtain three number ones from one album.

La Isla Bonita (from True Blue)


Written by Madonna • Patrick Leonard • Bruce Gaitsch

La Isla Bonita (which is Spanish for ‘The Beautiful Island,’) was a song that showcased Madonna’s versatility as an artist. Although she received criticism for cultural appropriation, the singer’s vocal delivery made it La Isla Bonita one of the standout tracks on the True Blue album. Released as the fifth and final single from True Blue, the song peaked at number four on the Billboard Hot 100.

La Isla Bonita was sampled for:

  • Spanish Fly by Black Rob & Jennifer Lopez
  • My Harlem Lullaby by Ma$e

Like A Prayer (from Like A Prayer, 1989)


Written by Madonna • Patrick Leonard

Like a Prayer is one song that has always stood out to me when it comes to Madonna’s catalog, and one song I was introduced to when it came to her as a whole. I grew up in a Baptist upbringing so gospel music means a lot to me. Like A Prayer can be interpreted in many ways, but has been described by Madonna as “a song of a passionate young girl so in love with God that it is almost as though he was the male figure in her life.”

The inclusion of double entendres in Like A Prayer can make the song sexual, religious or BOTH. A real music lover loves when a song can having multiple meanings behind it. Like A Prayer’s production is stellar and that’s why I love and admire Madonna as an artist. The influences of heavy rock, gospel, R&B and dance makes the song one of the most remarkable songs ever released. Released as the lead single of the album of the same name, Like A Prayer peaked at number one on the Billboard Hot 100, and number twenty on the Billboard R&B charts.

Like A Prayer was sampled for:

  • The Boss by Rick Ross and T-Pain

Express Yourself (from Like A Prayer)


Written by Madonna • Stephen Bray

Express Yourself is a quintessential female empowerment anthem, and is one of Madonna’s best songs period. From a lyrical perspective, the singer is giving a message to women to not settle for second-best, and tell those men to express what it is they want from them. The song was written in mind to pay tribute to the legendary funk band Sly & The Family Stone. Peaking at number 2 on the Billboard Hot 100, Express Yourself was also released as the second single from the album. It has left a huge impression and impact on artists who have came after Madonna.

Cherish (from Like A Prayer)


Written by Madonna • Patrick Leonard

Released as the third single from the album, Cherish has the singer yearning for a meaningful love affair that’s not casual. I love the 1960s inspired production, and Madonna’s vocals! Cherish peaked at number 2 on the Billboard Hot 100.

Vogue (from I’m Breathless soundtrack, 1990)


Written by Madonna • Shep Pettibone

Vogue was recorded for the soundtrack of the is one of the most legendary house music records ever released. The lyrics of escapism and elements of disco, house and the phenomenon of voguing on the ballroom scene has made the song one of the best dance songs and LGBTQ+ anthems of all time. Vogue peaked at number 1 on the Billboard Hot 100, and 16 on the Hot R&B Singles charts respectively.

Vogue has been sampled for:

  • Vou 787 by Bad Bunny
  • Deeper and Deeper by Madonna
  • Break My Soul (The Queens Remix) by Beyoncé and Madonna

Justify My Love (1990)


Written by Lenny Kravitz • Ingrid Chavez • Madonna

Justify My Love is a song of Madonna’s that introduced me to the genius of this amazing legend. From a lyrical perspective, Justify My Love challenges listeners to release their inner freak and women being in control sexually. The elements of hip hop, trip hop, and trance, makes it one of Madonna’s daring records.

Released as the first single from this compilation, the song was a commercial success despite the controversy when it came to the music video and musical lyrics. Justify My Love peaked at number 1 on the Billboard Hot 100, giving Madonna her 9th number one record. Also, fun fact: THE Lenny Kravitz wrote and produced this timeless record.

Justify My Love contains a sample of:

  • Security of the First World by Public Enemy

Justify My Love was sampled for:

  • Justify My Thug by Jay-Z

Waiting by Madonna

Rescue Me (1990)


Written by Madonna • Shep Pettibone

The album closes with Rescue Me, which was released as the second single from the compilation. Lyrically, the song is making allusions to rescue her from love. The gospel and house music influences makes the song more eventful and important to Madonna’s catalog. The song peaked at number 9 on the Billboard Hot 100.

Greatest hits albums are very complex and gives me the clarity I need when it picked out what the music consumer loves about it. One thing about Madonna that makes me love her artistically, is that she doesn’t allow anyone to put her in a box. The material listed on the track list for The Immaculate Collection will stand out for showcasing the most essential songs to her catalog. A masterpiece! -MW

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