Albums: Barcelona Gold (1992), Something to Remember (1995)
Songwriters/producers: Madonna/Shep Pettibone

The main reason why Madonna’s non-album tracks are so forgettable is, simply, because her instinct for self-editing is generally so spot-on. Naturally, there are plenty of examples from periods where she was overflowing with great material - but for each Into the Groove or Crazy for You, there are ten Supernaturals or It’s So Cools. Of course, good songwriting is more about an artist’s highs than the consistency of their every bootleg-recorded breath; no one is that good. So in retrospect, an offcut from Erotica - beloved by some, yet deeply inconsistent - from the soundtrack to a women’s baseball film doesn’t sound too promising. But at the time, as her first new material in over a year, This Used to Be My Playground became her tenth number one on the Billboard charts.

Despite being one of the last songs recorded during the Erotica sessions, This Used to Be My Playground stylistically had nothing to do with the then-upcoming album; its MOR balladry instead foreshadowed Madonna’s Something to Remember era three years later. Strangely, likely due to issues Warner had with Columbia/Sony distributing the film, its initial release was not on the soundtrack to A League of Their Own, but the entirely forgotten Olympic-inspired Barcelona Gold compilation.

Though Madonna’s previous musings on innocence in Live to Tell and Oh Father expressed a dark, yet incredibly complex range of emotions, This Used to Be My Playground simply wallows in the past. It’s not necessarily more sentimental than heartfelt, but there’s no sense of resolution, none of her trademark determination - just grey skies as far as the eye can see. As an artist who’s always steadfastly refused to look back or mythologise her own achievements, the self-indulgent nostalgia of “don’t hold on to the past/well that’s too much to ask” is thoroughly unconvincing. Shep Pettibone’s slightly plodding production - complete with stock pop-ballad strings and a synth-glockenspiel intro - only serves to push the song into borderline schmaltzy territory; something Madonna should always have been above. But she had much better songs up her sleeve - when literally half her singles that decade were to be ballads, she damn well needed them.

Director: Alek Keshishian

The video is nothing special - someone flips through a photo album as Madonna sings from the various pictures inside. Everyone involved is on autopilot; though the video obviously strives to depict snippets of memories, the scrapbook motif makes the budget look low, and Madonna static.

For once, Madonna’s cinematic ambitions here far outweigh her musical interpretation; A League of Their Own is, simply, a great film. Its solid, witty screenplay was exactly what Madonna’s last four major efforts lacked - and she held her own amongst the ensemble cast, her performance and the film her most critically acclaimed since Desperately Seeking Susan.

Given the prefeminist World War II setting, it’s easy to see why Madonna was eager for the part - with the men away and a female baseball league in demand, it was the perfect opportunity for women to express their talent in a traditionally male role whilst, most importantly, remaining themselves. Despite the patronising nature of making women’s baseball appealing, from etiquette classes to their impractical, skimpy uniforms, the players impress even where they don’t succeed. Dramatised or not, the film forces the audience to admit that the women of the real-life All-American Girls Professional Baseball League were, though not always intentionally, true pioneers - both athletic and feminist.

“What if at a key moment in the game, my uniform bursts open, and oops - my bosoms come flying out? That might draw a crowd, right?”
“You think there are men in this country who ain’t seen your bosoms?”
- Mae Mordabito (Madonna) and Doris Murphy (Rosie O’Donnell), not entirely acting

Madonna is cast perfectly as “All the Way” Mae Mordabito, something of an exaggeratedly promiscuous, 1940s baseballer version of herself - alongside Rosie O’Donnell, their brash charisma is a highlight of the first half of the film. But just as importantly, she knows her place despite her top billing, downplaying her role to make way for a fierce Geena Davis and a wonderfully over-the-top, immediately pre-fame Tom Hanks as manager. Director Penny Marshall offsets the action by bookending it with scenes of a fifty-years-later Hall of Fame reunion - though often derided for their sentimentalism, there’s nonetheless a truth in athletes (or anyone, really) wanting to relive their glory years. But as a now-and-then team picture fades into the credits over the strains of This Used to Be My Playground, one can’t help but feel the film ends on the wrong note. As with most sports movies, the point should be the glory of being, triumphing in the moment - but without the nuance of the past two hours, the final impression portrays it as a nostalgic period piece; saddened in the present, hence not quite uplifting enough. You’d think there’d be no one better than the real-life Madonna Ciccone to teach the value of that lesson.