When looking at her bigger career, there was no period in Madonna’s career that was full of scrutiny and reinvention quite like the 1990s. Starting with her appearance in the Oscar-winning Dick Tracy (1990), she began this decade with a juggernaut that inadvertently also launched one of her biggest singles with “Vogue.” With the documentary Truth or Dare (1991), she continued to explore the image of the promiscuous girl by discussing her bisexuality with an openness not often seen in mainstream pop culture.
She was the bad girl, capable of going on The Late Show with David Letterman to curse and ask the host to smell her panties. She could release sexually explicit books like “Sex” and have an engrossing, adult album like “Erotica.” Mind you, this was all in the first half of the decade, when it felt like she was spiraling out of control, where her desperation for shock value was overpowering her ability to be taken seriously as a musician.
It’s what her 1994 album “Bedtime Stories” symbolized, featuring a more mature and focused sound. Many considered it a positive turn in her career, where she was finally becoming a more tangible pop star worthy of the acclaim she had been receiving for a decade now. There was nothing wrong with the album, especially since it featured collaborations with Björk and Massive Attack and had surrealist music videos that showed her continuing to experiment with her vision.
Still, one had to ask what she had to do to be taken completely seriously. Given that she was about to start filming Evita (1996), she was finding herself at a point in her career where she wasn’t going to be touring. How was she going to keep the attention on her, capable of proving that she was more than a radical woman who had open discussions about her wild sex life for international audiences, with everyone from Pope John Paul II and K.F.C. boycotting her?
It came with her latest compilation “Something to Remember.” To be clear, I am not wanting to explore every compilation that Madonna has released because of the significant overlap of tracks. In fact, I didn’t cover “The Immaculate Collection” for this very reason (hot take: it has the definitive version of “Like a Prayer”). However, I looked at “Something to Remember” and found that while it had a significant amount of material that I already discussed, it also had these stray corners that I haven’t been able to talk about elsewhere. At least not without expanding the column to an unfeasible, tangential machine where I track down every soundtrack appearance she ever made.
That is why I’m doing “Something to Remember,” which was designed as her most novel career renovation yet. When you think of Madonna, you think of the big, bawdy hits that get the crowd dancing. Well, what this compilation suggested was that she was capable of oh so much more. She was a genuine singer, capable of finding some inner angst that drew her to ballads throughout her career. From “Like a Virgin” to “Bedtime Stories,” there was some evidence of her greater capability. Yes, even “Erotica” would get its day here. You see, Madonna was always talented. We just weren’t paying attention.
To quickly get through the old, there are a handful of album cuts that make a returning appearance here. The titular song “Something to Remember” is a reference to a song from “I’m Breathless” that didn’t get a lot of attention. Other tracks include “You Don’t Live Here Anymore” (“Like a Virgin”), “Live to Tell” (“True Blue”), “Oh Father” (“Like a Prayer”), “Rain” (“Erotica”), “Take a Bow” and “Forbidden Love” (“Bedtime Stories”). Some of these cases involved rewritten versions or musical interludes expanded upon to create more of a dramatic feel that played into Madonna’s downbeat style. The album also has the distinctiveness of not having a song shorter than four minutes with the longest being 6:23.
While it’s not the first appearance on a Madonna compilation, “Crazy for You” is an early standout that makes the cut here. The song was written for the film Vision Quest (1985) and may be one of her first great ballads. It still surprises me that it never appeared on a professional album until “The Immaculate Collection” because it perfectly embodies what early-era Madonna was capable of. The instrumentation may be sparse, the harmonies fleeting, but it’s this beautiful song that captures an intimacy that is often ignored in her career. It was also the first song to get her a Grammy Award nomination for Best Female Pop Vocal Performance and was her second number-one single on the U.S. Billboard Hot 100.
As far as expendable songs go, it’s difficult for anyone to refute this one’s quality. It’s echoic of the career to come. Even if it came during a time when she was seen as a lesser performer, more “Boy Toy” than a serious artist, she was providing a love song that had traces of passion. Ironically, it wasn't released as a single because it would distract from her “Like a Virgin” songs. It feels like a missed opportunity, but it only makes it more of a minor gem waiting to be discovered, especially since most people couldn’t even name the film this appeared in.
The other noteworthy soundtrack song that makes its presence here is “This Used to Be My Playground,” which accompanied A League of Their Own (1993). By this point, Madonna had transitioned into acting, so this credit had a duality to it. With that said, it’s maybe the most pretentious, satirical possible choice for this album. It’s so self-serious and goes on for two more minutes than it should. Maybe it’s just because it’s a credits song, but it could’ve been tighter. Still, the dramatic turn is beautiful enough to compliment the rest of this vision. Similar things can be said about “I’ll Remember,” which was featured in With Honors, capturing an equally reaching Madonna throwing her soul into this passionate number.
With the new music, she decided to collaborate with a series of producers. This included another project with Massive Attack called “I Want You.” It was a Marvin Gaye cover that found her reinventing the Motown singer’s style in a way that fit her vocal range. This wasn’t going to be just a pop tune. It was going to find her reaching for the heart and soul. There was an eagerness in her that also was reflected in the other new tunes “You’ll See” and “One More Chance.”
While “Bedtime Stories” could at least get by as having a wholly original collection of songs, this is difficult to find much to be enthusiastic about in terms of cultural cache. It’s true that it produced four singles, including a reissue of “Oh Father,” and would sell 10 million internationally. Its cover, shot while Madonna was at a shoot modeling Versace clothes, was considered to be one of the trendiest album covers in history by capturing the internal angst of Madonna as she leaned on a wall.
But otherwise, it’s mostly filler. The album exists as damage control since the road ahead was going to feature Madonna do everything to produce something more fulfilling with her career. It was a nice reminder of what she was capable of, making something more milquetoast and safe than even “Bedtime Stories” by removing any trace of salacious euphemism. This was an album you could play for your mom and not feel embarrassed. If anything, it was Madonna proving she was accessible.
Whether or not it’s true, the album feels like the most meticulous as well. As much as “Bedtime Stories” had done enough to make her seem friendlier, it would be strange to see her go from this to Evita. I guess it was too radical of a shift to see this performer who was still considered edgy lead a major production of a movie musical. She needed people to believe that she could sing “Don’t Cry for Me Argentina” without people thinking about that “Sex” book. You couldn’t necessarily escape it, but having this middle piece at least makes the journey somewhat more plausible.
Madonna was durable, capable of changing with the times. Gone were the days of “Erotica” and now she was going to try and be taken seriously. Even then, her ability to pull this off started a trend of ballad albums. Among noteworthy releases in the wake of “Something to Remember” was Elton John’s “Love Songs” and “Rod Stewart’s “If We Fall in Love Tonight.” In fact, it’s become normal for performers to release albums like this. Even when it was halfhearted, Madonna clearly was able to reshape the industry with her every decision.
What this album did was serve as a reflection on a decade of being much more versatile than we gave her credit for. As a performer who had reached a few misfires like “Erotica,” it was important to build her image back up, hopefully using the past few years as a lull that leads to some new creative peak. While evidence has shown that she’s still got another 25 years (probably more) of substance, it’s a time when she needed to prove she was so much more. You couldn’t dance forever. With her next project, she would be featured in another Oscar-winning movie with Evita, though as I will get into later it’s an odd beast when looking at it from the movie musical landscape. It’s good, but there is a reason that she hasn’t appeared in too many similar projects since.
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