Let's start off with a personal favorite of mine, written by a man who is also a personal favorite and performed by a star of whom I have a similarly high opinion. You may or may not remember Warren Beatty's 1990 B-movie Dick Tracy (a comic book movie made about ten years too early), but those for whom Madonna's acting career is defined by her Razzie-nominated turns in Swept Away and Die Another Day ought to Netflix it (well, that or A League of Their Own) for proof that the Material Girl is not totally incapable of acting. In Dick Tracy, Madonna does double duty as both supporting actress (playing femme fatale Breathless Mahoney...hey, it's better than Pussy Galore) and as a singer, providing most of the film's soundtrack of songs written by legendary Broadway genius Stephen Sondheim (Madonna's soundtrack album I'm Breathless featured songs from and inspired by the film). There are a number of standouts, naturally, but the one the Academy chose to honor with the 1990 Oscar for Best Original Song was the slinky, sultry (and oh-so-cleverly titled) "Sooner or Later (I Always Get My Man)."
Madonna performed the song at the ceremony on March 25, 1991, and video clips of the performance are still available across the web. It really is an endearing performance to watch, not only because Madonna is surprisingly compelling live, but because the Queen is so obviously nervous as hell: her hands shake nearly the entire number and her voice quivers just slightly as she begins the number. In a recent interview with Entertainment Weekly, longtime showrunner Bruce Vilanch recalled the star collapsing into his arms the second she'd gotten off stage, shaking and relieved to be finished (he also said he was perhaps the last man in the world who could fully appreciate having Madonna collapse in his arms). After you check out the studio recording, take a peek at the video, and see for yourself what fireworks can come of the world's biggest pop star singing a song by the world's greatest theatrical songwriter.
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