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16. "Justify My Love"
Perhaps the R&B rumbling of "Justify My Love" (set off by a sample of Public Enemy's instrumental "Security of the First World") could be considered one of Madonna's more influential musical moments, but the impact of "Justify My Love" has more to do with the Visconti-inspired, MTV-banned video than the song itself. It's a sinister track with a libidinous performance from Madonna, but the influence of co-writer Lenny Kravitz makes it feel more like an interesting collaboration than a definitive Madonna statement.