In The Number Ones, I’m reviewing every single #1 single in the history of the Billboard Hot 100, starting with the chart’s beginning, in 1958, and working my way up into the present.
Madonna definitely thought of herself as a movie star. She looked like a movie star. She dated movie stars, and her first husband was a movie star. For a hot minute in the late ’80s, Madonna had enough juice to get a movie greenlit. But Madonna never truly became a movie star herself. Her acting career never quite became anything other than a part-time hobby.
In 1985’s Desperately Seeking Susan, her first real movie role, Madonna played a sort of cartoon version of her pop-music persona. The film did fairly well, and Madonna was a revelation in it. But after Susan, Madonna made a much-publicized pair of critically-detested flops, Shanghai Surprise and Who’s That Girl. 1990’s Dick Tracy was a pretty big hit, and it got some extra publicity from Madonna’s tabloid-friendly relationship with co-star Warren Beatty. One of the songs on Madonna’s tie-in album I’m Breathless was the Stephen Sondheim-written “Sooner Or Later,” which won an Oscar, and another was “Vogue,” one of Madonna’s biggest hits. She’s good in Dick Tracy, too. But Dick Tracy was less movie-star showcase and more comic-strip spectacle.
The closest that Madonna ever came to real-deal movie stardom, I’d argue, was two years after Dick Tracy. By that point, she’d also been in the Woody Allen joint Shadows And Fog and the sensationalistic tour documentary Truth Or Dare, neither of which really helped her case for movie stardom. (She may have actually hurt that case by clowning Kevin Costner in the most famous scene from Truth Or Dare, even though that was obviously awesome.) In the summer of 1992, though, Madonna played a supporting role in Penny Marshall’s A League Of Their Own, a charming picture that also became a runaway hit.
A League Of Their Own is a fictional fairytale story about the real-life All-American Girls Professional Baseball League, which started in 1943 and ended about a decade later. Madonna is third-billed in the movie, behind only Tom Hanks and Geena Davis, but she doesn’t really have the third-biggest role in the picture. Instead, Madonna is mostly comic relief, and she’s good at that. Madonna and Rosie O’Donnell get a nice little repartee going, and she has fun stealing a couple of scenes as the boy-crazy center fielder “All The Way” Mae Mordabito. She’s not the emotional core of anything, but she shows up and does her job. Madonna’s place on the poster for A League Of Her Own says less about the film and more about Madonna’s place in the cultural imagination circa 1992. She couldn’t be the star of a movie like that, but she could be a star. She could help sell some tickets.
A League Of Her Own took in about $108 million at the domestic box office — just slightly more than Dick Tracy had made two years earlier. It’s still Madonna’s biggest Hollywood hit, unless you want to count her fencing-instructor cameo in the 2002 James Bond movie Die Another Day, which I do not. A League Of Their Own was also the 10th-biggest movie of 1992. It made less than Wayne’s World or Basic Instinct, but it made more than Unforgiven or The Hand That Rocks The Cradle.
Madonna wasn’t exactly in love with A League Of Their Own. Later in 1992, she told The Guardian, “I think it’s cute. It’s not Gone With The Wind, it’s not Doctor Zhivago, it’s no work of art. It’s entertaining, light. There’s some funny moments. It’s very sweet… I mean, the true story is fascinating and amazing, but I think it’s been candy-coated.” Madonna also didn’t seem to think too much of the film’s end-credits song, even though that song became her 10th chart-topper.
Penny Marshall’s idea for the League Of Their Own soundtrack was that it should feature current artists singing songs from the era. That’s sort of what happened, though it would probably be stretching things to say that James Taylor and Art Garfunkel were current artists in 1992. Madonna didn’t take part in that whole exercise. When the people at Columbia reached out to ask Madonna for a song, she and “Vogue” producer Shep Pettibone were in the middle of their work on Erotica, the album that she’d release later in 1992. Erotica is a deeply horny deep-house concept album, and it has basically nothing to do with A League Of Their Own, but Madonna and Pettibone knocked something out in a few days.
Does anyone associate “This Used To Be My Playground” with A League Of Their Own? I don’t. I barely remember that the song and the movie had any relationship. A League Of Their Own is an antic gee-whiz period piece about triumphant women in a different time, while “This Used To Be My Playground” is a morose torch ballad. Also, nobody ever refers to a baseball field as a “playground.” There’s some sad nostalgia at the end of League, so maybe “Playground” didn’t make a terribly incongruous end-credits song. But I just don’t associate that song with Tom Hanks yelling that there’s no crying in baseball. They exist completely independently of each other in my mind. There’s no overlap. Maybe that’s me.
In that Guardian interview where she more or less dismissed A League Of Their Own, Madonna did the same thing for “This Used To Be My Playground”: “They wanted me to write a song for the movie; I can do that sort of thing real easy. I call it assignment writing.” When she took on that assignment, she and Shep Pettibone had just finished their work on “Rain,” the Erotica ballad that would later peak at #14. Madonna had sung plenty of slow songs before “Rain,” but ballads were a new thing for Shep Pettibone, a club producer who was still in high demand as a remixer even after “Vogue.”
The night after they got the request for a soundtrack song, Pettibone came up with a backing track for another ballad. Madonna listened and came up with an idea. Two days later, Madonna and Pettibone had written “This Used To Be My Playground.” On the song, Madonna’s narrator wallows in nostalgia and resists the idea that she should not wallow in nostalgia: “Say goodbye to yesterday/ Those are words I’ll never say.” She’s singing about being unable to get over a breakup, which is not an issue facing any of the characters in A League Of Their Own. (In the movie, Bill Pullman plays the husband of Geena Davis’ main character Dottie Hinson, and he’s notably supportive of her baseball dreams. No breakups there.)
Madonna’s “Rain” is a pretty slick early-‘90s club ballad, but on “This Used To Be My Playground,” you can really hear that Pettibone wasn’t especially comfortable with the form. Pettibone had never worked with actual instruments before recording “Playground,” and it shows. On the day that they recorded it, he and Madonna decided that the strings sounded bad, and they raced to fix the arrangement, finishing it just in time to avoid paying overtime to the orchestra that they’d hired. The day after she finished it, Madonna flew out to the set of her next movie, the erotic-thriller flop Body Of Evidence.
“Playground” has none of the dreamy sweep of older Madonna ballads like “Crazy For You” and “Live To Tell.” Instead, it sounds cheap and chintzy. The strings are maudlin. The piano is canned. The central hook is strong enough that they maybe could’ve turned it into a club ballad like “Rain,” but that wasn’t the assignment. Instead, “Playground” sounds like Madonna in an adult-contempo stupor.
“This Used To Be My Playground” is exactly the wrong song for a singer like Madonna. In its glassy texture, “Playground” sounds like something that a grand ‘90s balladeer might sing, but Madonna is not a grand ’90s balladeer. She doesn’t have the pipes of a Whitney Houston or a Celine Dion, and she doesn’t have that kind of hammy squaresville delivery, either. She can’t make the song dramatic, and she doesn’t really try. Instead, she tries to give the song a poised, understated reading, but there’s no spirit in her delivery, no personality. She also over-enunciates a bit — a possible early warning of the fake British accent that she’d start using in the years ahead. (For my money, the exaggerated New York accent that she uses in A League Of Their Own is way more charming.)
It’s kind of funny that Madonna teamed up with Shep Pettibone, a producer whose club tracks generally sounded pretty futuristic, on two #1 hits from the soundtracks of two period-piece movies. But then, Madonna’s whole deal is, at least in theory, some combination of old-Hollywood glamor and chameleonic post-disco trend-humping. On “Vogue,” Madonna and Pettibone found a beautiful balance. On “This Used To Be My Playground,” they missed it wildly. “Playground” sounds like what it is: a rush-ordered for-hire job that was clearly just a quick cash-in for Madonna. Even the video for “This Used To Be My Playground” is half-assed. It’s just Madonna made up to look like moving pictures in a photo album, and it’s boring. (Director Alek Keshishian had already made Truth Or Dare, and he’d go on to helm 1994’s With Honors.) Boy George got mad because that video ripped off his clip for the 1987 solo single “To Be Reborn.” In his memoir, he referred to Madonna’s clip as “This Used To Be My Video.”
“This Used To Be My Playground” barely edged into #1 during a time when, thanks to new SoundScan tabulation methods, songs were topping the Hot 100 for longer and longer stretches. “Playground” got a Golden Globe nomination but no Oscar nod, and Madonna never sang it live even once. Because of label issues, “Playground” didn’t appear on the League Of Their Own soundtrack album. Until Madonna released the 1995 ballad collection Something To Remember, the only album that included “Playground” was Barcelona Gold, a compilation released to tie in with the 1992 Olympics. (I guess some Olympic sports are played on playgrounds.) Maybe that scarcity helped sell a few “This Used To Be My Playground” singles, and maybe those sales helped the song reach #1. In any case, it’s really not one of Madonna’s immortal hits.
When “Playground” made it to #1, it marked Madonna’s 10th time reaching the top. That made Madonna the female solo artist with the most #1 hits. It broke a tie with Whitney Houston, who would catch up soon enough, with some help from Madonna’s sworn enemy Kevin Costner. Around the same time, Madonna signed a lucrative new deal and launched her Warner imprint Maverick, which had a whole lot of success with records from Candlebox and Alanis Morissette. (I don’t know how involved Madonna was with day-to-day Maverick business, but it would be pretty cool if it turned out to be her idea to sign the Prodigy and Deftones and Bad Brains.)
Madonna may have been eager to distance herself from A League Of Their Own and “This Used To Be My Playground” because they clashed so badly with what she was trying to do with Erotica. Madonna released Erotica in October of 1992 — the same time that she released her much-hyped photo book Sex. The press treated both the album and the book as if their mere existence was scandalous, which was probably one of the main reasons that Madonna made both of them in the first place. Erotica isn’t up to the standards of Like A Prayer, Madonna’s previous studio album, but it’s still a smooth, elegant work of house-pop, and it’s never gotten the respect that it deserves.
Erotica and Sex marked the breaking-point moment that some vast swath of the public started wishing that Madonna would just relax. Backlash was in the air. Erotica sold double platinum, half of what Like A Prayer had done three years earlier. None of the singles from Erotica topped the Hot 100, though a couple of them broke into the top 10. The album’s funky, breathy title track found Madonna bringing back her “Justify My Love” fuck-mutter delivery, and it sure sounds like it’s at least partly about pegging. Maybe the world wasn’t entirely ready for that. The song peaked at #3. (It’s a 6.) Madonna followed that single with the lush, booming “Deeper And Deeper,” which peaked at #7. (It’s an 8.)
With the performatively horny trilogy of Erotica, Sex, and Body Of Evidence, Madonna’s whole career took a hit. Her downturn came just as fellow ‘80s pop titans Michael Jackson and Prince were losing their own grip on dominance, but Madonna held on for longer than either of them. We’ll see Madonna in this column again.
BONUS BEATS: Here’s the cover of “This Used To Be My Playground” that a Flock Of Seagulls contributed to a Madonna tribute compilation in 2000:
(A Flock Of Seagulls’ highest-charting single, 1982’s “I Ran (So Far Away),” peaked at #9. It’s a 7.)
BONUS BONUS BEATS: Here’s Bizzy Bone sing-rapping over a sample of “This Used To Be My Playground” on his 2001 solo track “Jesus”:
(As a member of Bone Thugs-N-Harmony, Bizzy Bone will eventually appear in this column.)