We Picked Madonna's Top 20 Singles to Celebrate 35 Years Since Her DebutEXPAND
Mert Alas and Marcus Piggot

We Picked Madonna's Top 20 Singles to Celebrate 35 Years Since Her Debut

It's hard to believe that at the beginning of 1982, the world didn't know who Madonna was. She would soon come to dominate the next three and a half decades, changing the landscape of pop music with her chart-topping singles, boundary-pushing music videos and Broadway-caliber concerts. Indeed, 35 years ago it all started with Madonna's first ever single, "Everybody." To celebrate its anniversary, L.A. Weekly has chosen the Material Girl's top 20 best singles. (Ed. note: The list is not based on chart success.)

20. "Miles Away" (2008)

The third single from Madonna's Hard Candy album may not have gotten much radio play, but it is quintessential Madonna. Co-produced and co-written by Timbaland and Justin Timberlake, the song foreshadowed things to come in Madonna's marriage to then-husband Guy Ritchie. "When I'm gone, you realize/That I'm the best thing that happened to you," she sings atop one of Timbaland's signature beats.

19. "Ghosttown" (2015)

The second single from Madonna's most recent album, Rebel Heart, is a beautiful, edgy ballad with a chorus so catchy it'll be stuck in your head for days. The song surely would have been a huge smash for a younger pop star, but alas radio showed it no love. Even Diplo, who co-produced "Rebel Heart" but not "Ghosttown" (Jason Evigan helmed this one), told Rolling Stone, "No one seems to want [Madonna] to succeed. ... 'Ghosttown' was a guaranteed No. 1 for anyone else but she didn't get a fair shot." The music video, which featured a beautiful tango with co-star Terrence Howard, just adds to the majesty of the song.

18. "Papa Don't Preach" (1986)

While "Like a Virgin" definitely stirred some controversy two years prior, no one was expecting pop music's It girl to release a song about a woman telling her father that she's pregnant and choosing (key word) to keep the baby. As Madonna told Rolling Stone in 2009, "[The song] just fit right in with my own personal zeitgeist of standing up to male authorities, whether it's the pope or the Catholic Church or my father and his conservative, patriarchal ways." Produced by longtime collaborator Stephen Bray and released as the first single off the True Blue album, "Papa Don't Preach" showed the world that Madonna was ready to talk about more than being a Material Girl.

17. "Secret" (1994)

"Secret" was the first single off Madonna's Bedtime Stories album, her dip into the world of R&B. Co-produced by R&B mega-producer Dallas Austin, the mystery of the song continues to have fans guessing to this day just what the secret is (popular choices include being pregnant, finding out about a lover's child or coming out). The beautiful black-and-white video, shot in Harlem and featuring everyone in the neighborhood from drag queens to teenagers, just added to the song's intrigue.

16. "Dress You Up" (1985)

The final single off Madonna's smash Like a Virgin album, "Dress You Up" is a fun, bubbly pop song produced by former Chic band member Nile Rodgers. While the song seems squeaky clean by today's standards, it was included on the Parents Music Resource Center's "Filthy 15" list. PMRC founder Tipper Gore said she considered the lyrics "Gonna dress you up in my love" to be vulgar. "Popular culture is morally bankrupt ... and Madonna is worst of all," Gore said. The movement led to the creation of the parental advisory sticker.

15. "Frozen" (1998)

"Frozen" found Madonna in perhaps her greatest reinvention: a post-motherhood, Kabbalah-studying yogi, experimenting in the world of electronica. Co-produced by two of Madonna's best producers, longtime collaborator Patrick Leonard and British electronica producer William Orbit, "Frozen" is a beautiful, haunting ballad complete with an orchestral string section — a departure from the dance hits of her earlier career. The memorable video, shot in the Mojave Desert, featured a majestic Madonna in all black morphing into crows, dogs and multiple versions of herself.

14. "Rescue Me" (1991)

One of two new songs on Madonna's first greatest-hits compilation The Immaculate Collection (the other being the No. 1 hit "Justify My Love"), "Rescue Me" was a preview of things to come on Madonna's Erotica album, featuring a poetic, spoken-word style set against a blazing up-tempo house beat. "Rescue Me" may not be the most famous Madonna song (nor did it even get a video), but it was innovative for its time and perfectly bridges the gap between '80s and '90s Madonna.

13. "Borderline" (1984)

"Borderline" was the last single from Madonna's self-titled debut album and was Madonna's first top-10 hit in the United States ("Lucky Star," which was released as a single before "Borderline," actually hit the top 10 after that song did). Produced by Reggie Lucas, the song has had incredible staying power, most recently being prominently featured in an episode of the "Will & Grace" revival earlier this year. When the song was released, it seamlessly paid homage to the disco sounds of the '70s while foreshadowing the '80s synth-pop Madonna would come to be known for. The music video, the first of many that Madonna had Mary Lambert direct, depicts the star as a commoner picked up by a photographer who puts her on a magazine cover, mimicking her burgeoning popularity in real life.

12. "Music" (2000)

After the success of Ray of Light, Madonna continued to explore her electronica side with its follow-up, Music. Released as the first single, the title track is a funky, electro-pop song with a futuristic folky sound — "acid rock," as Madonna says on the track. France's Mirwais Ahmadzaï produced the song (and album), helping to cement Madonna as the queen of reinvention and getting the Material Girl her first No. 1 single in six years. The music video, which featured Madonna dressed as a pimp in the back of a limo and Sacha Baron Cohen's Ali G character as the limo driver, helped make "Music" one of Madonna's most iconic singles. 

11. "Into the Groove" (1985)

Recorded for Madonna's big feature film debut, Susan Seidelman's Desperately Seeking Susan, the song ultimately did not appear on the soundtrack despite being prominently featured in the film. Instead, it was included on the reissue of the Like a Virgin album. Produced by Stephen Bray, to this day "Into the Groove" continues to be known as one of Madonna's signature songs and a definite fan favorite.

10. "La Isla Bonita" (1987)

The final single from Madonna's True Blue album appears to be one of her favorite songs, as she's included it in the set list on many of her world tours. The song was co-produced by famed Madonna collaborator Patrick Leonard as a tribute to her Latin American fans. Featuring Spanish guitars, Cuban drums and maracas, "La Isla Bonita" was the first of many times throughout her career that Madonna would be inspired by the Latin community. The video, also directed by Mary Lambert, similarly showcased the song's Latin inspiration, with Madonna appearing as a flamenco dancer, one of two characters she plays in the clip.

9. "The Power of Good-Bye" (1998)

The third single from Ray of Light is a beautiful ballad featuring electronica elements. Co-produced by Ray of Light captain William Orbit and longtime collaborator Patrick Leonard, its heartbreaking lyrics explore the themes of detachment and letting go of a love. The music video, helmed by acclaimed video director Matthew Rolston, uses the same themes as the song's lyrics. Its blue-green tint adds to the drama, as does Madonna and her lover's game of chess, inspired by The Thomas Crown Affair.

8. "Deeper and Deeper" (1992)

The second single off Madonna's Erotica album fuses disco and house-pop. Co-produced by the man behind almost all the songs on the album, Shep Pettibone, "Deeper and Deeper" ends with a call-back to Madonna and Pettibone's mega-hit "Vogue" from two years prior. The music video, directed by Bobby Woods, features Madonna playing a character based on Edie Sedgwick. However, according to Madonna collaborator Dan Cadan in the liner notes from 2001's greatest-hits compilation GHV2, the song itself is actually about a man coming to terms with his homosexuality. "I can't help falling in love/I fall deeper and deeper the further I go," Madonna sings in the chorus. It may be subtle, but if Cadan is correct, "Deeper and Deeper" is yet another example of Madonna's long support of the LGBT community.

7. "Take a Bow" (1994)

Madonna's longest-running No. 1 single on the Billboard Hot 100 chart, "Take a Bow" is an R&B-pop ballad co-produced by Kenneth "Babyface" Edmonds. Backed by a full orchestra, the second single from the Bedtime Stories album also finds influences in Japanese music. While the song itself is one of Madonna's most beautiful sonically, some of its success no doubt was linked to its cinematic music video. Helmed by Michael Haussman and filmed in Ronda, Spain, it features Madonna as the neglected lover of a Spanish bullfighter. "Take a Bow" proved that the Madonna of the '90s was just as much a force to be reckoned with as she was in the '80s.

6. "Holiday" (1983)

Another Madonna favorite to perform on tour (she's included it in eight out of her 10 world tours), "Holiday" was the third single released from her self-titled album. The previous two singles, "Everybody" and "Burning Up," failed to chart, making "Holiday" Madonna's first mainstream hit when it peaked at No. 16 on the Billboard Hot 100. Produced by John "Jellybean" Benitez, "Holiday" remains not only a signature song in Madonna's career but also a signature song representing '80s music as a whole. While it may not be as sonically sophisticated as some of Madonna's later music, its simple four-bar sequence, featuring synth, guitar, hand claps and a cow bell played by Madonna herself, has made "Holiday" a timeless classic.

5. "Express Yourself" (1989)

Long before Lady Gaga's LGBT-empowerment song "Born This Way" came Madonna's female-empowerment song "Express Yourself." Whether or not you considered "Born This Way" a reductive version of "Express Yourself," the Stephen Bray–produced song stands on its own as one of Madonna's best. The song, which brilliantly incorporates brass and saxophone, is considered by many to be a feminist anthem, with lyrics like, "Long stem roses are the way to your heart/But he needs to start with your head."

The video took these themes to a whole other level. Directed by David Fincher and inspired by the 1920s Fritz Lang film Metropolis, it depicts Madonna in chains in one scene while she wears a pantsuit and grabs her crotch in another. Half-joking about the scene where she crawls to a bowl of milk, Madonna told BBC Television in 1990 that the main theme of the video was that "pussy ruled the world." The song and video for "Express Yourself" represent quintessential Madonna: catchy, boundary-pushing pop with a message.

4. "Hung Up" (2005)

Madonna chose to follow up her personal and introspective 2003 album American Life with something a little more light and fun: 2005's Confessions on a Dance Floor. That album, which was co-produced by English producer/DJ Stuart Price, was an homage to the disco '70s. The album's first single, "Hung Up" brilliantly sampled ABBA's hit single "Gimme! Gimme! Gimme! (A Man After Midnight)," which Madonna personally asked the band for permission to sample. While the song and album were bigger hits overseas, "Hung Up" still managed to crack the top 10 on the Billboard Hot 100 chart as Madonna's 36th top-10 single. The music video, which paid tribute to John Travolta and memorably featured Madonna in a pink leotard, helped ensure that the single became a highlight of her career.

3. "Vogue" (1990)

Perhaps Madonna's most blatant love letter to the LGBT community, the song and music video paid tribute to the vogue dance style, which was becoming popular in the underground gay clubs of New York City. "Vogue" originally was meant to be a B-side to "Keep It Together," but record executives convinced Madonna it was too good for that. The song , which was co-produced by Shep Pettibone, went on to become the first single from Madonna's Dick Tracy soundtrack album, I'm Breathless. From the "Strike a pose" lyrics to the spoken name-check of golden-era Hollywood celebrities, "Vogue" is by far one of the biggest hits of Madonna's career. The famous black-and-white music video, directed by David Fincher, featured some of the original gay dancers who were vogueing as part of the gay ball scene, notably Jose Gutierez and Luis Camacho "Xtravaganza," (who also helped choreograph the video). "Vogue" is simply the cream of the crop in terms of pure pop perfection and has deservedly become an iconic part of pop culture.

2. "Ray of Light" (1998)

Perhaps the most electronic-sounding single from Madonna's dip into the world of electronica, "Ray of Light" brilliantly blended the lines between the genres of electronic dance, techno, trance and pop, opening the door for other pop artists to experiment in electronic music. Produced by William Orbit, the second single off the album is based on a 1971 folk song by Curtiss Maldoon called "Sepheryn." Different from anything Madonna had released in the past, the song still managed to hold onto her signature style, a truly astonishing reinvention for an artist who had just turned 40 and had been topping the charts for 15 years already. The music video, directed by Jonas Akerlund, shows "a day in the life of the earth," featuring time-lapse images of everyday life, spliced in with clips of Madonna dancing. It perfectly fit into Madonna's new, more down-to-earth image that accompanied the album. The song and video also helped Madonna win two Grammy Awards, for Best Dance Recording and Best Short-Form Music Video, her first Grammys since winning one for the Blond Ambition Tour earlier in the '90s (the Ray of Light album also won Best Pop Vocal Album). The "Ray of Light" single not only made Madonna relevant to a new generation but also reinvigorated her reputation as a pop music innovator and trendsetter.

1. "Like a Prayer" (1989)

"Like a Prayer" holds a place among the most iconic pop songs ever released. The first single from the eponymous album, and co-produced by Patrick Leonard, the song was considered at the time the most sophisticated single Madonna had released. Lyrically and musically, the song was more substantive than the simpler pop of her previous three albums. Musically the song blends pop and funk, throwing in a gospel choir and even a little R&B. Lyrically, the song mixes religious references with sexual undertones.

The music video, directed by Mary Lambert, caused quite a stir upon its release, even causing Pepsi to pull out of a multimillion-dollar deal it had with Madonna (she got to keep the money). A message about racism, the video featured Madonna getting intimate with an African-American saint. Later in the video, he is falsely accused and arrested for the murder of a white woman. Madonna then is seen dancing in front of burning crosses, an obvious reference to the KKK symbol of racism. The themes of the video are sadly still relevant today, yet Madonna was speaking to them at a time when not many mainstream white artists were. The song has rightfully been included on many best song lists, including Blender's "500 Greatest Songs Since You Were Born," Rolling Stone's "500 Greatest Songs of All Time" and even L.A. Weekly's "20 Best Pop Songs in History by Women Artists." The artistic caliber of "Like a Prayer" makes it the No. 1 single of Madonna's 35-year career.

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