FEATURE: Express Yourself: Madonna at Sixty: Her Finest Songs




Express Yourself


IN THIS PHOTO: Madonna on the T.V. programme, Saturday Show, in 1984/PHOTO CREDIT: Rex

Madonna at Sixty: Her Finest Songs


THIS time tomorrow…


IN THIS PHOTO: Madonna in Desperately Seeking Susan (1985)/PHOTO CREDIT: Rex

will see the Queen of Pop enter her seventh decade of life and it will be a big moment! If she were unhappy about turning sixty – and not willing to make a fuss – then I would feel guilty for publishing so much. In contrast, she is looking forward and planning a big shindig. It will be great to see her embrace her birthday. The music industry places emphasis on age and being ‘mature’ – signals that, once you get to a certain point, you need to slow it all down and be a bit quiet. In honour of the Pop legend turning sixty; I have selected her very best songs. Have a look at these tracks and maybe you disagree with the selection; you might have some personal opinions or want to cast your own vote. It is hard to narrow down the brilliance of her music but I hope, in this piece, I have gone some way to…

IN THIS PHOTO: Madonna performing on the Blond Ambition Tour (1990) in Tokyo, Japan/PHOTO CREDIT: Rex

HIGHLIGHTING the cream of the crop.





Released: 15th February, 1984

Album: Madonna (1983)

Trivia: The song became Madonna’s first top-ten in the U.S. on the Billboard Hot 100 and charted for thirty weeks. Borderline has been covered by the likes of The Flaming Lips and Duffy and the music video for the song is considered one of her finest and most enduring.

Like a Virgin

Released: 31st October, 1984

Album: Like a Virgin (1984)

Trivia: Like a Virgin was written by Billy Steinberg and Tom Kelly and was inspired by Steinberg’s time living in his father's Coachella Valley vineyard. Steinberg stated it was not intended for Madonna when he wrote it – it was based on his personal experiences. Producer Nile Rodgers did not want Madonna to record the song as he felt it was bubble-gum and there was no good hook (he grew to like the song!). Family organisations wanted the video and song banned because they felt Madonna was unsavoury and was promoting sex without marriage.  The song is listed in the Rock and Roll Hall of Fame’s list of 500 Songs That Shaped Rock and Roll – a satisfying middle-finger to those who snubbed and criticised the track!

Material Girl

Released: 23rd January, 1985

Album: Like a Virgin (1984)

Trivia: The music video was a mimicry of Marilyn Monroe’s performance of the song Diamonds Are a Girl’s Best Friend from the 1953 film, Gentlemen Prefer Blondes. Everyone from Britney Spears and Haylie Duff have covered the song and, despite it being considered one of her most iconic songs; Rikky Rooksby, in the book, The Complete Guide to the Music of Madonna, called it a “pungent satire on the Regan/Thatcher young-guns-go-for-it era” and stated that Pop music and irony do not mix!

Papa Don’t Preach


Released: 11th June, 1986

Album: True Blue (1986)

Trivia: The music video saw Madonna adopt a complete makeover. She got rid of the heavy jewellery and thrift store looks of previous shoots/videos and sported a more toned physique, cropped hair and a look that was described as a mixture of tomboy and Shirley MacLaine. The song hit the Billboard Hot 100 at number-forty-two and, within eight weeks of release, it had reached the top – making it Madonna’s fourth number-one single in the U.S.

La Isla Bonita

Released: 25th February, 1987

Album: True Blue (1986)

Trivia: Madonna co-wrote the song with Patrick Leonard. It was Madonna’s first single to incorporate Latino influences and the lyrics are a tribute to a beautiful island – Madonna has said it was a tribute to the beauty of Latinos. It became her fourth number-one in the U.K. and set the record for the most number-ones for a female artist. In the music video, Madonna plays two characters – a young, pious Catholic woman and a glamorous, passionate Latina.

Like a Prayer

Released: 3rd March, 1989

Album: Like a Prayer (1989)

Trivia: Although its video turned heads and caused some controversy, the song debuted the Billboard Hot 100 at number-thirty-eight and impressed critics who noted Madonna’s growing confidence and move from a more-simple Pop artist to someone able to fuse sweet-sounding elements with raw, sexual lyrics - a mixture of the sacred and profane. Like a Prayer has been featured during five of Madonna’s concert tours, most recently on the Rebel Heart Tour in 2015-2016.

Express Yourself


Released: 9th May, 1989

Album: Like a Prayer (1989)

Trivia: The video for the song was directed by David Fincher and was inspired by the Fritz Lang classic, Metropolis (1927). The video’s budget was $5 million which made it the most expensive video ever at that time – it is currently the third-mostexpensive of all time. Madonna’s inspiration behind the song was to express what you feel and not hiding it because, if you do not let it out, you will regret it. No matter how sexually confident you are in a relationship she said, there is that power struggle and compromise (that quote is attributed to the author Mick St. Michael).


Released: 27th March, 1990

Album: I'm Breathless: Music from and Inspired by the Film Dick Tracy (1990)

Trivia: Vogue is considered, musically and stylistically, a career highlight. The song remains one of Madonna’s biggest international hits and has topped the charts in over thirty countries. It became the world’s best-selling single of 1990 and sold over six-million copies. The video was directed by David Fincher and takes stylistic inspiration from the 1920s and 1930s. The video won three gongs at the 1990 MTV Video Music Awards and is seen as one of the greatest music videos ever.

Justify My Love


Released: 30th October, 1990

Album: The Immaculate Collection (1990)/B-side of Express Yourself

Trivia: Musically, Justify My Love is a Trip-Hop-inspired track with mid-tempo settings and instrumentation. The lyrics look, primarily, at sex and romance. Critics were mixed when the song was released but Justify My Love has been seen by contemporary critics as one of her very best. The track became Madonna’s ninth number-one and reached the top-ten in several countries.



Released: 29th September, 1992

Album: Erotica (1992)

Trivia: Like Justify My Love; Erotica experiments with Spoken Word and it (Erotica) is an ode to S&M – Madonna used the pseudonym, ‘Dita’.  In the song (and video), she asks her lover to be passive whilst making love to her and leads him to explore the boundaries of pleasure and pain.



Released: 5th August, 1993

Album: Erotica (1992)

Trivia: Rain was written and produced together by Madonna and Shep Pettibone. Madonna wanted the song for a musical adaptation of the 1939 film, Wuthering Heights, to be directed by Alek Keshishian. The video premiered on 21st June, 1993 on MTV and won two categories for Best Art Direction and Best Cinematography at the 1993 MTV Video Music Awards. It was ranked number-seventy on SLANT Magazine’s 100 Greatest Music Videos.

Take a Bow

Released: 6th December, 1994

Album: Bedtime Stories (1994)

Trivia: Produced by Madonna and Babyface; the song became Madonna’s eleventh number-one and received favourable reviews from critics – impressed by the poetic, soulful lyrics and mature sound. Take a Bow was backed by a full orchestra and it was the first time Babyface had worked with a live orchestra (per Madonna’s suggestion). The pentatonic strings give the song an impression of Chinese or Japanese Opera.

Human Nature


Released: 6th June, 1995

Album: Bedtime Stories (1994)

Trivia: A reaction to the pressure Madonna was getting regarding sexual content in her music; Human Nature is a shit against critics and their rather conservative attitude. It sees her at her most confident and brash as she counteracts fussy and ridiculous critisisms with an excepptional vocal peerforemance.


Released: 23rd February, 1998

Album: Ray of Light (1998)

Trivia: The first single from the critically-celebrated album, Ray of Light; Frozen is seen as a huge creative leap and masterpiece by critics. The video was directed by Chris Cunningham in the Californian desert and (the video) portrayed Madonna as a witch-like figure who shapeshifts into a flock of birds and a black dog. The song has been covered by artists such as Talisman and Thy Disease.

Ray of Light


Released: 6th May, 1998

Album: Ray of Light (1998)

Trivia: Another track from the Ray of Light album that gained massive critical love; the music video was directed by Jonas Åkerlund – who had previously directed the controversial Smack My Bitch Up video (The Prodigy). Madonna insisted the video should be edited in Los Angeles as, during the Frozen video, she had a number of back-and-forths with director Chris Cunningham (who was in London during the process) – something she was not keen to repeat.

The Power of Good-Bye


Released: 22nd September, 1998

Album: Ray of Light (1998)

Trivia: The Power of Good-Bye received acclaim from critics who recognised the track as one of Ray of Light’s best cuts. They praised Madonna going in an instrumental and Electronic direction and praised the strong and nuanced vocals. The song attained commercial success across Europe and reached the top-ten in charts of over nine nations.


Released: 21st August, 2000

Album: Music (2000)


Music was inspired by a Sting concert Madonna attended and was written and produced by her with Mirwais Ahmadzai. It is a Disco/Electro-Funk song in the static key of G minor and Madonna’s vocals are electronically manipulated in the track – the lyrics have political and social undertones. The video sees Madonna and her friends enjoying themselves in a limousine driven by Ali G. Critics noted the use of American image in the video – especially with Madonna’s cowboy imagery and clothing.

What It Feels Like for a Girl


Released: 17th April, 2001

Album: Music (2000)

Trivia: The song opens with a Spoken Word sample by actress Charlotte Gainsbourg – taken from the 1993 film, The Cement Garden. The music video was directed by her then-husband Guy Ritchie and premiered on 22nd March, 2001. It features Madonna on a reckless crime spree – causing MTV to ban the video before the 9.00 P.M. watershed.

Hung Up


Released: 17th October, 2005

Album: Confessions on a Dance Floor (2005)

Trivia: The famous ABBA (instrumental) sample we hear on Hung Up is from their hit, Gimme! Gimme! Gimme! (A Man After Midnight). Many critics felt Madonna has suffered a creative slump during her 2003 album, American Life, and were back on-board with this song. The music video is a tribute to John Travolta and his dancing films - whilst the song became Madonna’s thirty-sixth top-ten song.

Bitch I’m Madonna


Released: 15th June, 2015

Album: Rebel Heart (2015)

Trivia: Although the song sees a fair few co-writers in the mix (including SOPHIE and Maureen McDonald); Bitch I'm Madonna talks of Madonna having fun because of who she is – not really caring about age, limitations and opinions. Many critics were offended by the usage of the word ‘bitch’. Madonna shot back and was annoyed. She realised that word could be taken out of context and offensive but, in her song, it was a more affectionate and harmless term.