Trying to rate the 25 best songs in Madonna's vastly celebrated and legendary catalog was not easy. But for those just getting into the Material Girl after all these years, we feel it's a good start.
From the beginning, essentially, Madonna's music was made for dance clubs. As time passed, she remained a serious presence within the pop, dance and electronica musical worlds. This title cut from her seventh studio album pretty much has all the bases covered when it comes to those aforementioned genres, as well elements of techno, trance and disco. Though "Ray of Light" did not top the Billboard Hot 100, it was nominated for three Grammy Awards, and won for Best Dance Recording and Best Short Form Music Video.
Always willing to branch out, whether via her look or music, Madonna continues to be an influencer. It can be argued that this plucky number from her 1986, third studio album True Blue truly increased her popularity among Latin listeners and audiences at the time. A top five-hit on the Hot 100, "La Isla Bonita" has been critically considered the gem of the True Blue album, while proving Madonna can dabble in just about any type of sound and succeed.
Another instance of Madonna highlighting a woman's authority. This time, presumably, in a sexual relationship, still lending a voice for female empowerment that became part of her persona as she continued to dominate the pop culture scene at the dawn of the 1990s. The house-fueled, sultry and steamy "Justify My Love" — which went to No. 1 on Billboard's Hot 100 and debuted as part of her 1990 greatest hits album The Immaculate Collection — was co-written by Lenny Kravitz and is one of her more experimental tracks.
"Holiday" might have been the third single released from Madonna's self-titled, debut album in 1983, but it became her first song to crack the top 20 on the Billboard Hot 100. Thus, making it her breakthrough single, and introducing the mainstream music world to a bright, young pop artist who was ready to throw caution to the wind and take on the world. It was also an early sign that she would succeed in crossing multiple musical genres, notably pop and dance.
Released as a double-sided single with the aforementioned "Holiday," "Lucky Star" has a disco vibe that fueled Madonna's rise. And, not just from a musical standpoint, though it was a top-five Hot 100 hit. It was one of her early music videos that exemplified the fashion force she would become, setting clothing and accessory trends like semi-mesh tops, black boots, bulky socks, multiple bracelets — and, of course, lace-fingerless gloves that had tweens, teens and 20-something girls combing suburban shopping malls to copy Madonna's look.
From the very beginning of her stardom, Madonna has been a major influence and inspiration for female entertainers that have followed. Her confidence and strength paved the way for the likes of M.I.A. and Nicki Minaj to succeed. Their own personal strengths and embodiments of female empowerment were reasons why Madonna chose to work them on this snappy, upbeat top-10 hit that is essentially a celebration of her iconic and legendary status as a performer.
1989's Like a Prayer, Madonna's fourth studio album, was an attempt to prove that she was maturing, both as an artist more than capable of remaining at the top of her game without sticking to the same teen-focused brand of pop, and a person, who is confident and strong. "Express Yourself" is the perfect example of all that, with Madonna's turning the corner as an artist and person, willing to grow and still prosper. The single reached No. 2 on the Billboard Hot 100.
Madonna ushered in the 2000s amid a sea of younger, popular solo female artists who were taking the pop world by storm. However, she was still the queen of pop, and dance-pop, electronica, etc. The title track from her eighth studio album proved that Madonna would remain a force in the music world, worthy of praise from those she helped guide and inspire — even if only indirectly — to their own professional fame. "Music" was another No, 1 single for Madonna, who also received Grammy nominations for Record of the Year and Best Female Pop Vocal Performance.
The 1987 comedy Who's That Girl, which Madonna starred alongside Griffin Dunne, was panned by critics, and a box-office bomb. However, the film's title song ended up being Madonna's sixth No. 1 single on the Billboard Hot 100. Sharing a somewhat similar Latin vibe with the aforementioned "La Isla Bonita," "Who's That Girl" earned a Grammy Award nomination in the category of Best Song Written for Visual Media and a Best Original Song nom at the Golden Globes.
Known for its sampling underlay of ABBA's "Gimme! Gimme! Gimme! (A Man After Midnight)," "Hung Up," from her 10th studio album Confessions on a Dance Floor, paid homage to the pop dance tracks of the late 1970s and into the '80s. While it's not full-on disco, there is a serious nod to that genre as well. Of course, Madonna does it with the same panache and flair that's made her an icon. The track was a top-10 hit in America, and topped the Billboard dance charts in the United States, as well.
Not only did Madonna star in the 1992 Penny Marshall-directed A League of Their Own, starring Tom Hanks, but she co-wrote and performed the theme song for the popular flick. The song relates to the fictionalized account of the movie's story about the All-American Girls Professional Baseball League, showcased during World War II and beyond. Madonna earned a Golden Globe Award nomination for the song, and it remains, perhaps, her most accessible mainstream tune.
The lead single from Madonna's second studio release Like a Virgin, which made her an international superstar. One of the more creative tracks (with the robotronic voice repeating 'living in a material world') in Madonna's catalog, and a single that helped pave the way toward the artist achieving icon status. In fact, the title soon became her nickname, even though she was self-driven and confident enough to look past material attraction. Known for its Marilyn Monroe-homage music video, "Material Girl" peaked at No. 2 on the Hot 100.
One of the lighter numbers from Like a Prayer, "Cherish" peaked at No. 2 on the Billboard Hot 100 for Madonna. Reportedly inspired by classic love stories — the song even offers a nod to Romeo and Juliet — Madonna has always been a romantic at heart, though she's offered different ways of expressing that feeling. It's a simple song that proves she can have a little fun, and the listener doesn't need to dissect the song to the hilt — like critics of the superstar regularly did at the time.
The title cut from Madonna's aforementioned third studio album, "True Blue" is a rather uplifting song, at least in terms of drawing essentially no controversy. Well, other than the fact the tune is about Madonna's fancy for then-husband Sean Penn. The 1950s, doo-wop vibe and stylized music video make it one of her more positive songs, which made many teen girls of the 1980s want to sing into a hair brush in their bedrooms — probably like their mothers did. The track reached No. 3 on Billboard's Hot 100.
One of five singles from True Blue, and yet another No. 1 hit for Madonna. Fans of the Material Girl know this exceptional pop ballad was included in the edgy 1986 crime-drama At Close Range, which starred the aforementioned Sean Penn. It was a solid, and rather refreshing, departure from Madonna's dance-heavy hits of the day. Co-written with longtime collaborator Patrick Leonard, "Live to Tell" also showed the strides Madonna was making as a successful songwriter.
There might not be a more '80s song in Madonna's vast and legendary musical arsenal than this number from True Blue. The pulsating drum machine and chime-like brilliance of synthesizers and keyboards, dominate the song. Another popular dance track from Madonna, "Open Your Heart" was a No. 1 hit, and the highlight of a record that proved to more than hold its own as the follow-up to her iconic Like a Virgin release.
Here we go again — more queen of pop music controversy. It might be hard to pick just one Madonna song that had suburban moms wincing and radio stations wondering if they should play her music. However, this Madonna tale of teen pregnancy (from True Blue) — and what to do about it — stands out among the rest. Looking back, the subject matter seems rather tame today (or maybe not in certain political circles), but back in the 1980s, when radio and MTV were impressionable on teenagers, it was quite the big deal. Meanwhile, Danny Aiello was brilliant in the music video.
With a heavy influence from Latin music and the release one can get from working the dance floor, Madonna struck gold again with "Into the Groove." The single gained popularity through its inclusion in the 1985 comedy-drama Desperately Seeking Susan, which Madonna co-starred alongside Rosanna Arquette. As legend goes, Madonna originally wrote it for a musician acquaintance, then opted to make it her own, for the purpose of the movie soundtrack. It was also Madonna's first single to hit No. 1 in the United Kingdom.
Madonna teamed with Kenny "Babyface" Edmonds for this classic pop ballad that can be found on her 1994 Bedtime Stories album. The tune, and said album, offered a softer, more safe side to Madonna, who further pushed the envelope on her previous release, the sexually-charged Erotica (1992). And, in many circles, Bedtime Stories, and the No. 1-hit "Take a Bow," specifically, were welcomed by mainstream pop fans — especially those who tired of the controversy and shock value that Madonna seemed to thrive on during the 1980s, and into the early '90s.
There are certain songs that transcend the musical world and become iconic amid the realm of pop culture. "Vogue" is one of them. In some ways, Madonna's No. 1 track from her I'm Breathless record, in association with the Dıck Tracy film she starred alongside Warren Beatty, is a way of life. The song was inspired from the dance move known as "voguing," and popular within the gay underground club scene, especially in New York. Madonna had a massive gay following, and "Vogue" opened that aspect of her fan base to the masses. The memorable black-and-white music video, directed by the legendary David Fincher, received nine nominations at 1990 MTV Video Music Awards.
One of Madonna's more unheralded tracks. The final released single from Like a Virgin, "Dress You Up," was a top-five hit for Madonna, but not enough critics consider it to be among her classic hits, and it was never celebrated as much as the other two significant hits from the record. Heavy on synthesizer work, "Dress You Up" is mainstream pop at its best — catchy, with a refreshing rock element, and filled with the right amount of sexual innuendo to send conservative mothers across America into a tizzy.
Michael Jackson solidified himself as the "King of Pop" and the biggest entertainer on the planet in 1983, but Madonna was not too far behind. As noted, her 1983 self-titled debut was a massive hit, and "Borderline," with its accompanying music video, portrayed Madonna as an empowered female, who was not afraid to do what — and be with whom — she wanted, all while not being held to a lower standard in a seemingly male-dominated world. It was Madonna's first single to crack the top 10 of Billboard's Hot 100, and fueled the rest of the album's success.
Vision Quest is one of the greatest sports movies of all time (try to prove us wrong). And, a lot has to do with the music. It can be argued that the star of the soundtrack is this soulful ballad, which was No. 1 on the Billboard Hot 100 and a popular homecoming and prom theme throughout the U.S. In fact, we heard there were even couples who played the song as their wedding-day first dance. It was a rare tamed-down moment for Madonna, who actually performs the song in the movie.
Once again, Madonna found herself amid controversy with the release of the title cut from her fourth album. However, the issue with "Like a Prayer" was the popular music video. It was attacked for being inappropriate and sacrilegious, even drawing attention from Pope John Paul II, who called for its boycott. It featured an interracial love story and pushed an envelope that the superstar had not gone to before, but intended all the way. However, it remains one of the most infamous but creative and compelling music videos ever, and the semi-epic track was another No. 1 hit for the Material Girl. Pepsi even got in on the fun.
As noted, Madonna's sophomore release remains one of the greatest, and most influential albums of all time. The title track leads the way, and is the track that truly set the table for what Madonna was all about — and still is. Poppy and catchy enough to be a mainstream hit that spanned musical tastes, while also showing the artist was not about to play it safe when it came to her music, lyrics and fashion. If the music and pop culture world hadn't noticed Madonna up until then, they did after "Like a Virgin," her first single to top the Hot 100, took over the world.
A Chicago native, Jeff Mezydlo has professionally written about sports, entertainment and pop culture for parts of four decades. He was an integral member of award-winning sports sections at The Times of Northwest Indiana (Munster, Ind. ) and Champaign (Ill
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