FEATURE: Cherished: Madonna’s Essential Twenty Singles

FEATURE:

 

 

Cherished

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IN THIS PHOTO: Madonna shot for Cosmopolitan in July 1987

Madonna’s Essential Twenty Singles

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AS the iconic Madonna

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IN THIS PHOTO: Madonna in 2018/PHOTO CREDIT: Paul Zimmerman/Getty Images

celebrates her birthday on 16th August, I am putting out a few features. For this one, I am collating, in my view, her twenty best singles. It is hard to narrow down the list, as she has released eighty-eight singles and twenty-four promotional singles! That said, there are some that are definitely better than others. Here are my rankings regarding the very best singles from the Queen of Pop (I am considering promotional singles alongside standard singles). Some might disagree with my placements – we all have our views on the singles that are the great and those which are average. As you will see from the rundown and rankings below, Madonna has produced some of the best Pop music…

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IN THIS PHOTO: Madonna in the video for Take a Bow (from 1994’s Bedtime Stories)

WE have ever seen.

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20. Nothing Really Matters

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From the Album: Ray of Light (1998)

Release Date: 2nd March, 1999

Producers: Madonna/William Orbit/Marius De Vries

Critical Reaction:

Stephen Thomas Erlewine from AllMusic, Kevin C. Johnson from the St. Louis Post-Dispatch and Chris Gernard from Metro Weekly highlighted "Nothing Really Matters" as one of Ray of Light's best tracks. Erlewine, who also wrote Madonna's biography for the website, cited the song as one of her career standouts. Chuck Taylor from Billboard labeled the song as a "gem" and commended the "irresistible hook".From the same publication, Jason Lipshutz commented, "What if the suave dance of 'Nothing Really Matters', the eye-popping 'Ray of Light' music video or the stark beauty of 'Frozen' never existed? Luckily, we never need to find out." Paul Moody from NME noted that the song "floats by almost as if it's asleep, a knowing return to the disco diva-effortlessness of 'Vogue', but with Madonna free from the narcissistic outer-shell of old, free to announce: "I've realised/No-one wins..." Rolling Stone said, "Songs like the title track and 'Nothing Really Matters' are filled with warmth and wonder.” "A bubbly, infectious piece of shufflebeat…" Stuart Maconie wrote in a Q review of Ray of Light, "but aberrant items continually swim into view, like a tumbling, atonal piano solo right out of Schoenberg." Sunday Mirror said it is the "best pop tune" from the album. Stephen Thompson from The A.V. Club was positive, stating that the "chugging" chorus and composition "should ring across dance floors for years to come[...]" Nathan Smith from the Houston Press was also positive, stating, "Few singles illustrated [Madonna's change in musical approach] better than 'Nothing Really Matters'". He concluded, "It's a great, bouncy dance track that never received the love it deserved, and its family-friendly themes are a good fit for the event" – Wikipedia

US Billboard Hot 100 Position: 93

19. Erotica

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From the Album: Erotica (1992)

Release Date: 29th September, 1992

Producers: Madonna/Shep Pettibone

Critical Reaction:

Erotica" received generally positive reviews from music critics. Stephen Thomas Erlewine from Allmusic highlighted the song as an album standout, calling it "some of Madonna's best and most accomplished music". Larry Flick from Billboard described it as a "sexy pop/hip-hop gem" and a "sensual slice of aural sex." He added, "With the aid of collaborator Pettibone, she has crafted a deep and complex arrangement rife with intriguing Middle Eastern influences." Randy Clark from Cashbox commented, "Okay, there's nothing new musically on this virtually melody-less, "Vogue'-esque single, although the Material Girl does seem to want to continually push the barriers out a little further (fortunately, there’s not much further to go)." Alan Jones from Music Week said it "takes up the story where Justify My Love left off. The same hypnotic Soul II Soul shuffle underpins the moaning, groaning superstar as she raps/sings what are faintly ludicrous lyrics." Rolling Stone's Arion Berger wrote: "'Erotica' [...] promise[s] a smorgasbord of sexual experimentation, like the one portrayed in the video for 'Justify My Love'. But the sensibility of 'Erotica' is miles removed from the warm come-ons of 'Justify', which got its heat from privacy and romance [...] The Madonna of 'Erotica' is in no way interested in your dreams; she's after compliance"; he called the song "'Vogue' with a dirty mouth, where all the real action's on the dance floor". Stephen Holden from The New York Times, commented that the "foggy growl" that Madonna uses in the spoken-word sections of the song "contrast dramatically with the shrill little-kid voice from Madonna's earliest records that she still often uses to project a bratty teen-age exuberance". J. Randy Taraborrelli, author of Madonna: An Intimate Biography, wrote that "['Erotica'] wasn't a surprise for anyone who had been paying attention to Madonna's recent music. She had shown her hand earlier with Breathless when she sang 'Hanky Panky', the song about spanking [...] then there was her single 'Justify My Love' [...] 'Erotica' though, was the full-blown music exploration, an exhibition, of what we were to believe was Madonna's sexual reality". Authors Allen Metz and Carol Benson, called it "a bondage update on 'Justify My Love'". Matthew Jacobs from The Huffington Post, placed it at number 23 of his list "The Definitive Ranking Of Madonna Singles"; Jacobs wrote "Released at the apex of Madonna's sex appeal, 'Erotica' and its accompanying title album are remarkable as a period of innovation for the singer" – Wikipedia

US Billboard Hot 100 Position: 3

18. Beautiful Stranger

From the Album: Austin Powers: The Spy Who Shagged Me (soundtrack, 1999)

Release Date: 19th May, 1999

Producers: Madonna/William Orbit

Critical Reaction:

Beautiful Stranger" received generally positive reviews. Chuck Taylor from Billboard denoted the song as a "new shift in the wind for [Madonna]", calling it another creative high for her. He also complimented the production saying that "this latest partnership with [Orbit] taps into a walloping romp of guitars and enough cascading organs to prompt an urge to listen to your Monkees collection." Taylor ended the review with positive feedback for Madonna's vocals, likening them to those for the Evita album, along with commending the chorus. In a different article for Billboard talking about the song's remixes, Paoletta described the track as "effervescent blast of psychedelic electronica". Writing for the Philippine Daily Inquirer, Gino DeLa Paz found it "cute but forgettable". Gwen Ihnat, from the entertainment website The A.V. Club, labeled it as "Madonna's best song that never appeared on one of her regular albums [...] a psychedelic pop confection that offered a few of her most indelible hooks". Ihnat also wrote that "although less ethereal than 1998's Ray of Light, ['Beautiful Stranger'] is just as dance-floor ready [...] dance flute has never sounded so enticing, and Madonna's voice so sweetly seductive".  AllMusic's Jose F. Promis listed the track "as one of the singer's more memorable moments, coupling 1960s go-go rock with 1990s electronica, resulting in nothing less than a true slice of old fashioned rock & roll"; Promis also praised the two Calderone mixes” – Wikipedia

US Billboard Hot 100 Position: 19

17. Hung Up

From the Album: Confessions on a Dance Floor (2005)

Release Date: 17th October, 2005

Producers: Madonna/Stuart Price

Critical Reaction:

 “Hung Up received critical acclaim. Keith Caulfield from Billboard, while reviewing Confessions on a Dance Floor, called the song "a fluffier cut". Chris Tucker from Billboard explained that "Madonna returns with a song that will restore faith among her minions, fans of pop music and radio programmers". Jon Pareles of The New York Times said that Madonna kept her pop touch in "Hung Up" and called it a love song which is both happy as well as sad. Alan Light from Rolling Stone called the song candy coated. David Browne from Entertainment Weekly was impressed by the song and said "'Hung Up' shows how effortlessly she [Madonna] can tap into her petulant inner teen". Sal Cinquemani of Slant Magazine compared the song to the remix of Gwen Stefani's 2004 single "What You Waiting For?". Ed Gonzalez from the same magazine called the song the biggest hit of her career. Margaret Moser from The Austin Chronicle said that the song strobes and pulses along with another album track "Forbidden Love". Peter Robinson from The Observer commented that "Hung Up" is Madonna's "most wonderfully commercial single since the mid Eighties". Alexis Petridis from The Guardian called the track a "joyous...single that could theoretically have been more camp, but only with the addition of Liza Minnelli on backing vocals and lyrics about Larry Grayson's friend Everard” – Wikipedia

US Billboard Hot 100 Position: 7

16. Justify My Love

From the Album: The Immaculate Collection (greatest hits collection, 1990)

Release Date: 6th November, 1990  

Producers: Lenny Kravitz/André Betts

Critical Reaction:

 “Justify My Love" received acclaim from many music critics. In a separate review from AllMusic, they gave the song four-and-a-half stars out of five, stating "[Justify My Love] stands as one of the best of Madonna's long history of well-packaged maxi-singles, and further helped set a precedent for the maxi-single market." Larry Flick from Billboard commented that "her steamy collaboration" with Lenny Kravitz "has the juice to become the '90s equivalent" of Donna Summer's "Love to Love You Baby". He noted that "the chameleonlike singer writhes and whispers on top of a sparse, hypnotic hip-hop beat that strays miles away from the chirpy pop of her past. Break a sweat." In a review from Entertainment Weekly by David Browne, he gave it a positive remark saying that people who have a "hoo-haa" surrounding the banning of the single "underestimate her". Music & Media commented, "The unlikely collaboration of Madonna and Lenny Kravitz is a marriage made in heaven. Kravitz brought that beat back, while Madonna's sultry moans would make the Pope faint with certain desires. Atmospheric, yet brutal in an unconventional manner, this record whispers the word SEX very loudly and very convincingly. Most of all, it's a gutsy product.” Music Week called it a "mumbling sexy judderer". Rolling Stone said that the song and contemporaneous Rescue Me were "worthy sensual newies". While reviewing Celebration, Bill Lamb from About.com said "Songs such as "Justify My Love" that sounded a little over-indulgent when first released have worn very well over time." Alexandra Capotorto from PopCrush.com said "'Justify My Love' is perfectly constructed lovemaking music. While this track might be oozing sex, it's the NSFW music video that caused the most drama [...]" – Wikipedia

US Billboard Hot 100 Position: 1

15. Borderline

From the Album: Madonna (1983)

Release Date: 15th February, 1984  

Producer: Reggie Lucas

Critical Reaction:

 “Author J. Randy Taraborrelli, in his biography of Madonna, called "Borderline", along with "Holiday", the two key recordings that helped establish Madonna's base in the music industry. He added that Madonna's sober voice made the track "as close to an old Motown production as a hit could get in the dance-music-driven eighties." Author Maury Dean, in his book Rock 'n' Roll Gold Rush, called the song "echoey boogie" with "saucy-style and come-hither magnetism." Author Rikky Rooksby in his book, The Complete Guide to the Music of Madonna, called it harmonically the most complex track of her debut album. Stephen Thomas Erlewine from AllMusic called the song effervescent. Sal Cinquemani of Slant Magazine called the song soulful. Commentator Dave Marsh in his book, The Heart of Rock & Soul, said that the "music's too damn good to be denied, no matter whose value system it disrupts." Journalist Roxanne Orgill in her book, Shout, Sister, Shout!, commented that "Borderline" was the song that made Madonna the star that she is. Thom Duffy of Orlando Sentinel commented that "Borderline" was a song that "introduced Madonna, the helium-induced pop star, and a siren kitten” – Wikipedia

US Billboard Hot 100 Position: 10

14. Into the Groove

From the Album: Desperately Seeking Susan (soundtrack, 1985)

Release Date: 15th July, 1985  

Producers: Madonna/Stephen Bray

Critical Reaction:

 “Ever since its release, "Into the Groove" has received critical acclaim. J. Randy Taraborrelli, author of Madonna: An Intimate Biography, said that the song demonstrated Madonna's ability to create infectious dance music. Rikky Rooksby, author of Madonna: the complete guide to her music, said that "'Into the Groove' will make you feel like you're a winner either way. And that's one of the best things pop music can do for ya. [It's] Madonna's first great single." Clive Barker and Simon Trussler, authors of New Theatre Quarterly, felt that the song was the first disco-anthem of the 1980s.

Toby Cresswell, author of 1001 Songs: The Great Songs of All Time and the Artists, Stories and Secrets, said that the song is a "sweet, limited white tune on the top, and there's Madonna – all the right-shop chic – dragging the straight world into this subterranean paradise. All the magic of the eighties is right here." Matthew Rettenmund, author of Totally Awesome 80s: A Lexicon of the Music, Videos, Movies, TV Shows, Stars, and Trends of that Decadent Decade, declared "Into the Groove" as the ultimate 1980s song and felt that it "cemented Madonna's place as the dancing queen of the era". Dawn Keetley and John Pettigrew, authors of Public Women, Public Words: A Documentary History of American Feminism, called it a "mesmerizing theme song" – Wikipedia

US Hot Dance Club Songs (Billboard) Position: 12

13. Cherish

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From the Album: Like a Prayer (1989)

Release Date: 1st August, 1989  

Producers: Madonna/Patrick Leonard

Critical Reaction:

 “Wayne Robins from Newsday believed that "Cherish" exemplified the "kind of random pop we'd get if [postmodern author] William Burroughs were the program director of a Top 40 radio station." Burt compared the song and Madonna's delivery of the lyrics with the dialogues spoken by Shakespeare's Juliet, and found similarity in the, "Sweet so would I, Yet I should kill thee with much cherishing" from the play, with the lyrics of "Cherish". Allen Metz, one of the authors of The Madonna Companion, felt that "Cherish" as the opening song of the B-side of Like a Prayer, reaffirmed the sweet and happy romanticism that was missing from the A-side of the album adding, "As much a child of pop as of the church, Madonna is restored by music's healing power, in this case with a mixture of classic sweet soul and L.A. pop moderne."

Music critic J. D. Considine, while reviewing the Like a Prayer album for Rolling Stone complimented the song for creating an effective balance, contrasting its lighthearted nature with the trauma of "Oh Father", the next song. Considine also found retro-rock references in the song. Freya Jarman-Ivens, one of the authors of Madonna's Drowned Worlds, felt that the song was one of the last works on pure romanticism by Madonna. "She should come back to the formula from time to time, but I guess she has moved beyond all of that", Jarman-Ivens added. Carol Clerk, author of Madonnastyle noted that the "refreshing" nature of the song was particularly noticeable if one follows Madonna's catalog chronologically, especially embedded between the anthem like nature of the previous release, "Express Yourself", and the lament of the succeeding release, "Oh Father” – Wikipedia

US Billboard Hot 100 Position: 2

12. Express Yourself

From the Album: Like a Prayer (1989)

Release Date: 9th May, 1989  

Producers: Madonna/Stephen Bray

Critical Reaction:

 “Biographer Mary Cross noted in her book Madonna: A Biography, how the song paved the way for its music video and became a testament to freedom Authors Allen Metz and Carol Benson noted in their essays on Madonna, how she decimated "patriarchal, racist and capitalist constructions", by the way she pronounced the word "self" in "Express Yourself". They added that the opening line "Don't go for second best, baby" transformed the song into a postmodernist anthem. Scholar Sheila Whiteley noted in her book Women and Popular Music: Sexuality, Identity, and Subjectivity, that Madonna's acknowledgment of the pastiche and of being capable of imitating musical style was interesting to her, but given Madonna's ability to manipulate image, the musical exuberance of "Express Yourself" did not appear surprising.Mark Bego, author of Madonna: Blond Ambition declared that "the song that most reflected the Madonna everyone had come to know and be shocked by was 'Express Yourself'." O'Brien was impressed with the song, and gave a detailed review:

"Express Yourself" is a feminist call to arms, complete with muscular brass-playing and soulful voice. Here Madonna is the anti-materialism girl, exhorting her audience to respect themselves. That means having a man who loves your head and your heart. If he doesn't treat you right (and here's the revolutionary rhetoric) you're better off on your own. Like a female preacher, Madonna emphasizes each word of the chorus, invoking God and the power of orgasm. In parts Cosmo-woman, girl-talk, and swinging dance track, it presages the deliciously declarative stance of "Vogue" and shows Madonna moving from introspective to survivalist mode” – Wikipedia

US Billboard Hot 100 Position: 2

11. Like a Prayer

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From the Album: Like a Prayer (1989)

Release Date: 3rd March, 1989

Producers: Madonna/Patrick Leonard

Critical Reaction:

 “Following the release of "Like a Prayer" on March 3, 1989, it received widespread acclaim from critics, journalists and academics. Taraborrelli commented that the track "deserved every bit of the curiosity it generated. While being devilishly danceable, the song also shows Madonna's uncanny ability to inspire strong, conflicting emotions during the course of a single song, leaving the listener scratching his head for answers—and craving for more.” Stephen Holden from The New York Times, while writing about Madonna's re-invention of her image, observed how her sound had changed from the "simple blaring dance-pop to the rich, fully rounded pop of 'Like a Prayer'". Lucy O'Brien felt that the most remarkable aspect of "Like a Prayer" was Madonna's usage of liturgical words. "There is the surface meaning, forging sexuality with pop lyrics that sound so sweet. But underlying that is a rigorous mediation on prayer. In shorter words, 'Like a Prayer' really takes you there," she concluded. This view was shared by Mary Cross, who wrote in her biography of Madonna that "the song is a mix of the sacred and the profane. There-in lies Madonna's triumph with 'Like a Prayer'. It still sounds catchy and danceable."

From the academic world, positive reviews came from Michael Campbell, author of Popular Music in America: And the Beat Goes On, who felt that the soothing melody of the track resembles British singer Steve Winwood's 1986 single "Higher Love". The author noted the song for merging disparate and contradictory musical features in it. He found that the simple melody of "Like a Prayer" offered an easy listen, but the contrasts in sound, rhythm and texture appealed to different target audiences. Australian rock music journalist Toby Creswell wrote in his book 1001 Songs that "'Like a Prayer' is a beautifully crafted devotional song in the guise of perfect pop. God is the drum machine here." Scholar Georges Claude Guilbert, author of Madonna as Postmodern Myth: How One Star's Self-Construction Rewrites Sex, Gender, Hollywood and the American Dream, noted that there is a polysemy in "Like a Prayer" since the singer addresses either God or her lover, and in doing so "Madonna achieves the gold-card of attaining her own divinity. Whenever someone calls her name, it alludes to the song". Theologian Andrew Greeley compared "Like a Prayer" with the biblical Song of Songs. Greeley, although focusing more on the video, acknowledged the fact that sexual passion may be revelatory, and complimented Madonna for glorifying ideologies of female subjectivity and womanhood in the song” – Wikipedia

US Billboard Hot 100 Position: 1

10. Papa Don’t Preach

From the Album: True Blue (1986)

Release Date: 11th June, 1986

Producers: Madonna/Stephen Bray

Critical Reaction:

 “Papa Don't Preach" was met with acclaim from music critics. Davitt Sigerson from Rolling Stone magazine in a review of the album True Blue said that if there is a problem with the album "it's the lack of outstanding songs", adding that "only the magnificent 'Papa Don't Preach' has the high-profile hook to match 'Like a Virgin', 'Dress You Up' and 'Material Girl'.” In its review of True Blue, Allmusic's Stephen Thomas Erlewine said that "she is using the music to hook in critics just as she's baiting a mass audience with such masterstrokes as 'Papa Don't Preach'". Robert Christgau in a review for The Village Voice felt that "she [Madonna] doesn't speak for the ordinary teenaged stiff any more than Reagan speaks for the union members", adding that "while the antiabortion content of 'Papa Don't Preach' isn't unequivocal, and wouldn't make the song bad by definition if it were, the ambiguity is a cop-out rather than an open door, which is bad."

Sal Cinquemani from Slant Magazine said that "with songs like 'Papa Don't Preach', Madonna made the transition from pop tart to consummate artist, joining the ranks of 80s icons like Michael Jackson and Prince." David Browne from Entertainment Weekly in a review of her first compilation album The Immaculate Collection, commented that "In theory, a 30-ish urban sophisticate singing in the voice of a pregnant teen [...] ought to sound ridiculous", but added that "With the help of collaborators like Stephen Bray and Patrick Leonard, though, [the song] turns into a perfectly conceived pop record." In 2005, the same magazine placed the song at number 486 on its list of "The 500 Greatest Songs Since You Were Born". In 1987, the song was nominated for Best Female Pop Vocal Performance at the 29th Grammy Awards, but lost to Barbra Streisand's The Broadway Album” – Wikipedia

US Billboard Hot 100 Position: 1

9. Music

From the Album: Music (2000)

Release Date: 21st August, 2000

Producers: Madonna/Mirwais Ahmadzaï

Critical Reaction:

 “Upon release, the song received generally positive reviews from critics. J. Randy Taraborrelli, author of Madonna: An Intimate Biography, declared "Music" as a dance-anthem "that reaches into the future but also slyly conjures images and feelings of the good ol' disco days”. In a similar review, Lucy O'Brien, author of Madonna: Like an Icon, relegated the track as "a resurrection of the disco girl" image. She listed "Music" as a career-defining moment for Madonna, like previous singles "Vogue" and "Justify My Love" (both released in 1990). O'Brien clarified the song as "the same genre defining quality, robotic, tinny, trashy and audacious... She resurrects the Madonna imperative. Dance. Party. Surrender". Stephen Thomas Erlewine of AllMusic called it "a thumping track which sounds funkier, denser, sexier with each spin". Jim Farber of the New York Daily News gave a positive feedback, stating that it is "everything a single should be: pithy, simple and maddeningly catchy, her most instantly embraceable single since 'Holiday'". Farber also highlighted the lyrics, which he felt covered familiar ground for Madonna by talking about the power of dance music. This thought was shared by Fouz-Hernández, who believed that like her debut single "Everybody", "Music" defined Madonna's artistic credibility.

Reviewing the parent album for Rolling Stone, Barry Walters also compared it to Madonna's earlier work. Sal Cinquemani from Slant Magazine called it Madonna's best dance track since "Vogue", also comparing it to her 1985 single, "Into the Groove". In his review of Madonna's 2001 compilation GHV2, Cinquemani praised the single's "retro club beats and vintage synth sound". Giving it a B rating, he concluded that "only a former material girl living in a NASDAQ world could get away with a song like this". Dimitri Ehrlich from Vibe found "Music" to be "a bouncing parade of synthesizers that pose the question 'Do fortysomething baby-mamas still have the divine right to get down?' (The answer is yes)". Chuck Arnold from Entertainment Weekly, called it one of Madonna's "most eccentric hits ever" and found it to be reminiscent of her earlier works, specifically "Holiday” – Wikipedia

US Billboard Hot 100 Position: 1

8. Holiday

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From the Album: Madonna (1983)

Release Date: 7th September, 1983

Producer: John ‘Jellybean’ Benitez

Critical Reaction:

 “The song received critical acclaim. Author Rikky Rooksby in his book The Complete Guide to the Music of Madonna commented that "'Holiday' was as infectious as the plague. One listen and you could not get the damn hook out of your mind." He also likened the track as getting on a carousel and enjoying the ride, or get really bothered by the song going "on-and-on" for six minutes. Jim Farber of Entertainment Weekly commented that "Holiday" satisfied the musical ear of both the sides of the Atlantic. While reviewing The Immaculate Collection album, David Browne from Entertainment Weekly commented that "Holiday" was a "spunky dance-beat trifle". He also complimented the song's expert production. 

Mary Cross in her biography of Madonna, described "Holiday" as "a simple song with a fresh appeal and a good mood." According to author Lucy O'Brien, who wrote in the biography Madonna: Like an Icon, the track was an example of Madonna's early musical endeavors being about the "power of dance". She believed that the song cemented her style of music with its "bubbling Latin undertow, crunchy bass and strings and Fred Zarr's elegant closing piano riff". O'Brien declared "Holiday" as Madonna's "most" persuasive dance song with its "tension, release, resolution and celebratory" nature enhanced by Madonna's "playful commands and exhortations". Sal Cinquemani of Slant Magazine described the song as airy. Stephen Thomas Erlewine from AllMusic called it effervescent and one of the great songs of the Madonna album. While reviewing The Immaculate Collection, he called it one of her greatest hits. Don Shewey of Rolling Stone commented that the simple lyrics of the song sound clever” – Wikipedia

US Billboard Hot 100 Position: 16

7. Human Nature

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From the Album: Bedtime Stories (1994)

Release Date: 6th June, 1995

Producers: Madonna/Dave Hall

Critical Reaction:

 “Human Nature" received mostly positive reviews from music critics. Sal Cinquemani of Slant Magazine gave the song a positive review, stating that "for years, Madonna spoke in metaphors, fantasies and blatant shock tactics, but the performer indignantly struck back at her critics on 'Human Nature'. She didn't just hold up a mirror, she became the mirror". Barbara O'Dair from Rolling Stone also gave a positive review of the song, commenting that "Madonna does a drive-by on her critics, complete with a keening synth line straight outta Dre", adding that "Madonna's message is still 'Express yourself, don't repress yourself.' This time, however, it comes not with a bang but a whisper". Scott Kearnan of The Boston Globe included the track at number 11 on his list of "30 Ultimate Madonna Singles", stating that the line "Absolutely no regrets" was a "Madonna mantra if ever there was one". Medium's Richard LaBeau deemed it "one of Madonna’s best forays into R&B, this all-around-clever song features bold, unapologetic lyrics that serves as her unofficial manifesto".

Larry Flick from Billboard was also positive, and expected "radio to hungrily come to the table and dine on this wickedly catchy jeep/pop jam in which La M unapologetically snaps at her more close-minded critics". He complimented her vocals which were "playfully snide and aggressive, holding strong against a forceful hip-hop groove and a host of ear-pleasing funk guitar links and synth hoops". Music Week gave it four out of five, adding that "Maddy gets quirky on the hippest and most memorable track from Bedtime Stories". Author Chris Wade wrote in his book, The Music of Madonna, that "Human Nature" lifted the sadness emanated from the first few tracks from the album. "There's a great beat to this, a brilliant vocal where Madonna answers herself with whispers and an unforgettable chorus," Wade added. Matthew Rettenmund wrote in his Encyclopedia Madonnica that "in spite of the chart performance", the song has become a modern "self-empowerment anthem". Charles Aaron from Spin described the song as "slinking through [Hall's] low-ridin', gum-smackin' groove, Maddy's hard-bitten ingenue expresses no regrets, but this time you feel for her." Aaron highlighted the lyrics "Would it sound better if I were a man?" as subversive and coy. Author Lucy O'Brien described in her book, Madonna: Like an Icon, that "Human Nature" was one of the "quirkiest" tracks on Bedtime Stories, "throbbing with a tightly restrained but devastating anger” – Wikipedia

US Billboard Hot 100 Position: 46

6. La Isla Bonita

From the Album: True Blue (1986)

Release Date: 25th February, 1987

Producers: Madonna/Patrick Leonard

Critical Reaction:

 “Rikky Rooksby, in his book The Complete Guide to the Music of Madonna called the song "a little escapism". Dawn Keetley in his book Public Women, Public Words called the song one of Madonna's most perfect songs capturing her inner emotional life. William McKeen called the song "tranquil" and "Up on the Roof type imaginary escapes from the city snarl, the kind of Latin-flavored sweets that Blondie could never resist." Ken Barnes of Creem wrote the song is "no "Open Your Heart", but its lilting (yet reflective) quality transcends the south-of-the-border cliches."

Jon Pareles of The New York Times said that "La Isla Bonita" was one of Madonna's "friendlier" love songs. Don McLeese of the Chicago Sun-Times believed that the song was the best song on the album, as well as the most memorable. Meanwhile, Steve Morse of The Boston Globe believed that it was one of her "prettier" songs. Joey Guerra of the Houston Chronicle, while reviewing Madonna's Sticky & Sweet Tour, called the song a true retro one. Marty Racine, from the same newspaper, believed that the song was one that stood out on the album. Los Angeles Daily News, when discussing Madonna's style of music, believed that "La Isla Bonita" was a song that was "pointing in [a] welcome direction” – Wikipedia

US Billboard Hot 100 Position: 4

5. Material Girl

From the Album: Like a Virgin (1984)

Release Date: 30th November, 1984

Producer: Nile Rodgers

Critical Reaction:

Following the song's release on November 30, 1984, as the second single from Like a Virgin, "Material Girl" received mixed reviews from music critics. Author Rikky Rooksby, in his book The Complete Guide to the Music of Madonna, compared the song with those of Cyndi Lauper because of Madonna's shrill voice in the song. He added that the song was a "pungent satire on the Reagan/Thatcher young-guns-go-for-it era. Which just goes to show that pop music and irony don't mix." Stephen Thomas Erlewine from AllMusic said that "Material Girl" was one of the songs that made Madonna an icon, the other being "Like a Virgin" from the same album, both remaining as a definitive statement. He added that both tunes overshadow the rest of the record, "because they are a perfect match of theme and sound." Debby Miller from Rolling Stone, felt that the song portrayed Madonna as a more practical girl than previous female singers. Dave Karger from Entertainment Weekly, while reviewing the album in 1995, felt that the song came off a bit repetitious and immature when compared to the present context. Jim Farber from Entertainment Weekly felt that the song provided then critics a way to criticize Madonna's work. Sal Cinquemani of Slant Magazine commented that Madonna had "defined a generation with hits like 'Material Girl'." Alfred Soto from Stylus Magazine compared the song with "Everything She Wants" by Wham!. Michael Paoletta from Billboard commented that the song sustained a "fevered dance-rock momentum." Nancy Erlick from Billboard said that "singer and team conquer once more with their irresistible assembly of new and used pop hooks." In 2003, Madonna fans were asked to vote for their Top 20 Madonna singles of all time for a special issue of Q magazine dedicated to Madonna. "Material Girl" was allocated the 15th spot on the list” – Wikipedia

US Billboard Hot 100 Position: 2

4. Vogue

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

Release Date: 27th March, 1990

Producers: Madonna/Shep Pettibone

Critical Reaction:

Vogue" has been lauded by critics since its release. AllMusic critic Stephen Thomas Erlewine claimed that the song was "Madonna's finest single moment" and that it had an "instantly memorable melody". In a review of The Immaculate Collection, Erlewine also claimed that the song was "sleek" and "stylish". Jose F. Promis, in another AllMusic review, claimed that "Vogue" was a "crowning artistic achievement". Bill Coleman from Billboard commented that "the starlet's pop/house homage to the underground (soon to be pushed very overground) fad pulls off its aims." He stated that it "maintains the flavor of Pettibone's past "house" treatments with a bit of his classic "Love Break" tossed in for good deja vu measure." Ernest Hardy from Cashbox stated that "pop savvy takes well to a house setting", adding, "it's gonna be a Madonna Summer". Jim Farber from Entertainment Weekly, in a relatively negative review of I'm Breathless, asserted that the "finale of Vogue" is "the sole bright spot". David Giles from Music Week stated that "it possesses a meatier groove than we've been used to and also a silly "list" segment that reduces her to the level of the Beloved.” In his review of I'm Breathless, Mark Coleman from Rolling Stone wrote that, whilst the song initially sounded "lackluster", within the album's context, it "gains a startling resonance"]. Sal Cinquemani of Slant Magazine, in his review of the album as a whole, claimed that whilst the "hugely influential" song initially sounded "grossly out of place", it turns out to be "a fitting finale" for I'm Breathless. J. Randy Taraborrelli, in his book, Madonna: An Intimate Biography, wrote that the song was a "funky, uptown anthem celebrating the art of 'voguing'", as well as that the rap section "is still one of Madonna's greatest camp musical moments” – Wikipedia

US Billboard Hot 100 Position: 1

3. Ray of Light

From the Album: Ray of Light (1998)

Release Date: 6th May, 1998

Producers: Madonna/William Orbit

Critical Reaction:

Ray of Light" received acclaim from music critics. In a review of the album as a whole, Stephen Thomas Erlewine of AllMusic described it as "swirling". In a review of the maxi CD single, Liana Jonas of the same website called the track a "wickedly good club song" and "sonically progressive yet listener-friendly". She also praised Madonna's vocals, comparing them to those of a "club diva to celestial goddess". "The title track builds from another incongruously pretty guitar arpeggio into thumping rave anthem mode," Stuart Maconie wrote in a Q review of Ray of Light, "but always underscored with keen musical intelligence. It could be a lighter, less one-dimensional Chemical Brothers."

Larry Flick of Billboard described it as Madonna at her best, calling it a "spiritually charged, often poetic song". He especially mentioned the flexible vocals and Madonna's progression as a recording artist. Rob Sheffield from Rolling Stone in his review for the album as a whole, wrote that, alongside other tracks such as "Swim" and "Drowned World/Substitute For Love", Madonna is "positively ferocious" sounding on "Ray of Light". Sal Cinquemani of Slant Magazine wrote that the song was a "celebratory tech-frenzy", and noted Madonna's elated singing. In a review of Madonna's second hits compilation, GHV2 (2001), Cinequemani wrote:

Like no other Madonna hit in recent memory, the frenetic “Ray of Light” found the singer in a celebratory tech-frenzy. Whether it was an epiphany of the spiritual or sonic kind, her elation was unmistakable. Orbit’s cycles of analog synths and electric guitar licks perfectly supplemented the elasticity of Madonna’s newly-trained vocal chords. Not since “Deeper and Deeper” had she reached such dizzying heights” – Wikipedia

US Billboard Hot 100 Position: 5

2. Frozen

From the Album: Ray of Light (1998)

Release Date: 23rd February, 1998

Producers: Madonna/William Orbit/Patrick Leonard

Critical Reaction:

Jon Pareles from The New York Times was impressed how Madonna, dulcet and careful, performed the song. Joan Anderman from The Boston Globe said that on Ray of Light, only "Frozen" achieves a "state of divine balladry", recalls the "emotional pitch" and simmers the "beauty of 1986's 'Live to Tell' with a dark, lush string section, the smash and patter of a lone drum, and an ominous, pulsing buzz". In his review of Ray of Light, Neil Spencer of The Observer commented, "it's sensuous songs such as [...] 'Frozen' that stand out; music for the chill-out room." Elysa Gardner, writing in the Los Angeles Times, said "Madonna's enduring knack for incorporating hip and exotic textures into accessible pop tunes is evident on the plaintive single 'Frozen'". Sputnikmusic viewed the track as the singer "at her soothing best", highlighting its "interesting percussion backing" and "beautiful use of strings with techno effects".

David Browne of Entertainment Weekly described the song as a "wuthering-beats melodrama that's often breathtaking." Also from Entertainment Weekly, Chuck Arnold wrote: "sounding unlike anything Madonna had ever done before, and creating a mystical forest of sonic wonder — sweeping strings and all — 'Frozen' possesses an almost operatic grandeur that never fails to give you chills". Stephen Thompson from The A.V. Club wrote, "the atmospheric 'Frozen' is a great first single despite lyrics like, 'Love is a bird / She needs to fly.'" Conversely, NME called the song "another pile of her usual weepy old bollocks". Jim Farber of the Daily News wrote that "Frozen" compromises its electronic style with "too much tepid pop". The Guardian's Caroline Sullivan regarded it as a tremulous song Ray of Light could have done without. Jose F. Thomas from AllMusic rated the song two stars out of five, describing it as "chilly” – Wikipedia

US Billboard Hot 100 Position: 2

1. Take a Bow

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From the Album: Bedtime Stories (1994)

Release Date: 6th December, 1994

Producers: Madonna/Babyface

Critical Reaction:

Upon release, "Take a Bow" received general acclaim from critics. Peter Calvin from The Advocate praised the lyrical flow of the song, saying that the "effect is truly heartbreaking. The song... shows that ultimately Madonna... is just like you and me". Stephen Thomas Erlewine of AllMusic referred to "Take a Bow" as "tremendous", listing it as one of the best songs from Bedtime Stories and stating that it "slowly works its melodies into the subconscious as the bass pulses". He goes on to say that it "offer[s] an antidote to Erotica, which was filled with deep but cold grooves". Louis Virtel, from TheBacklot.com, placed "Take a Bow" at number 27 of his list "The 100 Greatest Madonna Songs". He wrote; "Madonna's most successful single to date is a melancholic evisceration of a lover's artifice, and its hopeless plain-spokenness makes it one of the finest examples of 90s balladry". J. D. Considine of The Baltimore Sun stated that the song, about "innocent romance" has a "gently cascading melody”.  In his review of Bedtime Stories, Billboard's Paul Verna called it a "holiday feast for Top 40, rhythm crossover, and AC". Also from Billboard, Larry Flick gave the single a particularly positive review; "The follow-up to the top five smash 'Secret' [...] is as perfect as top 40 fare gets. This single has a delightful, immediately memorable melody and chorus, engaging romance-novel lyrics and a lead vocal that is both sweet and quietly soulful. A lovely way for [Madonna] to kick out '95".

Rikky Rooksby, author of The Complete Guide to the Music of Madonna, was less impressed with the track. Although he felt that it sounded "shockingly normal" after the "ambient 'Bedtime Story'", he found the song's length as over-long and deduced it to be "communica[ting] no sense whatsoever of the pain of a real goodbye." In his 2011 review of Bedtime Stories, Brett Callwood of the Detroit Metro Times called the song "spectacular". Encyclopedia Madonnica writer Matthew Rettenmund called it a "sentimental ballad with showbiz theme" while finding similarities in the song to that of "Superstar" by The Carpenters. Writing for Entertainment Weekly, Chuck Arnold called it "one of the most elegant, most un-Madonna-sounding things she’s ever done". While ranking Madonna's singles in honor of her 60th birthday, Jude Rogers from The Guardian placed the track at number 38, calling it a "compellingly cinematic orchestral drama". Matthew Jacobs, from The Huffington Post, placed it at number 19 of his list "The Definitive Ranking Of Madonna Singles" calling it her "most poetic ballad". Bianca Gracie from Idolator noted it as a "timeless ballad", adding that it "has warm strings and soaring harmonies with a hint of tragedy from Madonna’s somber vocals, which makes the end result all the more beautiful." In his book, Madonna: An Intimate Biography, J. Randy Taraborrelli called it a "melancholy and beautifully executed ballad". Music & Media said it is "an elegant ballad, a perfect alternative to prosaic lullabies." They added, "The intro could be mistaken for jingle bells and fits in well with the season” – Wikipedia

US Billboard Hot 100 Position: 1