"Deeper and Deeper" is a song by American singer Madonna from her fifth studio album Erotica (1992). It was written by Madonna, Shep Pettibone and Anthony Shimkin, and produced by Madonna and Pettibone. It was released by Maverick Records as the album's second single on November 17, 1992. A shortened version of the song was included on Madonna's second greatest hits compilation, GHV2 (2001). "Deeper and Deeper" is a dance-oriented song, and features instrumentation from acoustic guitars and castanet beats on its bridge. Lyrically, the song talks about sexual desire, though it has been argued that it's actually about a young man coming to terms with his homosexuality.

"Deeper and Deeper" was met with positive reviews. Music critics hailed it as one of Madonna's strongest disco inspired tracks and complimented its refreshing dance oriented nature. It was also commercially successful; peaking at number seven on the Billboard Hot 100 and reaching the top ten in several countries including Canada, New Zealand, and the United Kingdom, while topping the charts in Italy.

The accompanying music video for "Deeper and Deeper" was directed by Bobby Woods. It was seen as a homage to American artist Andy Warhol and Italian director Luchino Visconti; it features Madonna playing a character based on Edie Sedgwick, who goes out to a nightclub to meet her friends and boyfriend. Madonna has performed "Deeper and Deeper" in three of her concert tours; on the 1993 Girlie Show World Tour, eleven years later on the Re-Invention World Tour (2004), and another eleven years later on the Rebel Heart Tour (2015–16).

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