My Top 5 Madonna Songs !

Updated on July 9, 2020
Madonna circa 1993
Madonna circa 1993

Honorable mentions :

Those would be in my Top 10 : Live to Tell, Like A Prayer, Holiday, Drowned World/Substitute For Love, Get Together

5. Nothing Fails (from American Life, 2003)

This song is an underrated gem from Madonna's equally underrated but uneven 2003 album American Life, which in my mind contained some of her very best and worst material. This is one of the best, as it remains one of her most touching tracks. The song is mostly acoustic and there is an impressive and unexpected gospel choir appearance, giving the song a sense of grandeur that is totally hair-rising. The poignant lyrics are sure to touch anybody who has a soul and Madonna's rendition is totally heartfelt. The song in its studio version was not a hit upon release but was strangely a club smash due to a number of great remixes available on the CD single. It is the only one in this list that has sadly never received a music video.

4. Justify My Love (from The Immaculate Collection, 1990)

Obviously Madonna's sexiest song. Few know that the song was written by Prince-protégé Ingrid Chavez, who released her own album, May 19, 1992, in which many tracks sound just like Justify My Love. Anyway, Madonna's delivery of the lyrics is sexually charged and pretty arousing. There is a dreamy quality in the music that makes the song stick in my head for a long time every time I have the joy to listen to it. The song was a huge hit, perhaps due to the attention its controversial accompanying music video received. Directed by Jean-Baptiste Mondino, it is my personal favorite and manages to be sexy without being pornographic, something pop stars of today should take note of. The song remains a Madonna classic and was featured in all her concerts since its release.

3. Hollywood (from American Life, 2003)

Another cut from American Life that nobody noticed upon release, Hollywood is to me a perfect pop gem and the quintessential track from the Madonna-Mirwais Ahmadzai collaboration. It is a perfect blend between a pop rock and folk song. The lyrics are as catchy as they can get and Mirwais's guitar work is incredible throughout the song, blending seamlessly with the electronica elements. Unlike other songs from the early 2000's, Hollywood still feels fresh today and could be released now. It was never performed in its complete studio version during one of her concerts, except for the short promo tour for the album back in 2003. The video is a fun one, directed again by Mondino and highlighting the highs and lows of Hollywood. This track deserves much more attention than it got and rightfully so remains a fan favorite.

2. Secret (from Bedtime Stories, 1994)

The Bedtime Stories album was significantly less adventurous than its 1992 predecessor Erotica as the album mostly contains love songs and has a warm R&B sound instead of raunchy lyrics over cold dance beats. The album is nonetheless an amazing listen and Secret remains one of Madonna's best. The song features a prominent acoustic guitar (something that was relatively new in a Madonna song until then) over a classic 90's R&B beat, but it somehow doesn't sound too dated. Madonna's vocal delivery is spot-on and the chorus is surprisingly soulful ; I can't help but hum every time I hear it. Secret was a hit on the worldwide charts and the single release notably contained excellent dance remixes by Junior Vasquez. The video, shot in Harlem in black and white, is quite sensual and displays Madonna at her most elegant, just like the song.

1. Deeper & Deeper (from Erotica, 1992)

The Erotica era (1992-1993) saw Madonna at her most controversial as she was trying to break all boundaries regarding sexuality, releasing her coffee-table book Sex, the Erotica album and the Basic Instinct-clone Body of Evidence around the same time. Despite the controversy that overshadowed Erotica (it sold significantly less than its predecessors), the music remained excellent and it is frequently listed as one of Madonna's best efforts by contemporary critics. I think Deeper & Deeper is Madonna's best dance song (yes, even surpassing Vogue) and one of the greatest early-90's club hits. The lyrics have a dual meaning, some saying it is about sexual desire or about learning to live with bisexuality. Anyway, the track remains a classic for the ages and is also a surprising one, as it features a flamenco guitar in the middle of it, something that would seem rather out of place in that kind of song but that feels right at home here. The accompanying video is very odd in every way possible and looks a bit like a home movie, making it unique and fun to watch. The cold dance beat is contagious and anybody who claims to be human will likely start to dance listening to it. It clearly is my case.


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    • Dianelle profile image


      4 years ago

      Hmmm I wonder why you mentioned mostly her sensually-sexual songs ;) she has so other great ones as well)


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