Deeper and Deeper

"Deeper and Deeper" is a song by American singer-songwriter Madonna from her fifth studio album Erotica. The song was released as the album's second single by Maverick Records. The song was written by Madonna, Shep Pettibone and Anthony Shmikin. It was produced by Madonna and Shep Pettibone and received generally favorable reviews from music critics at the time of its release. The song's accompanying music video received mixed reviews from both fans and critics alike, with some proclaiming it Madonna's most intriguing music video. "Deeper and Deeper" was released as the second official single from the album. It also appeared on her 2001 compilation album GHV2 in a shorter edit form.

"Deeper and Deeper" is a dance-oriented song. It also features other musical structures such as the use of acoustic guitars, with some Spanish, flamenco style lead and the use of castanet beats in the song's bridge. The song has been described by critics as "Pure Disco". Lyrically the song is a metaphor about a boy coming to accept his homosexuality. The song also shares similarities with Madonna's previous 1990 hit "Vogue" and also features a reference to "Vogue" towards the ending part of the song (the lyrics "You got to just let your body move to the music/you got to just let your body go with the flow" are taken from "Vogue"). There's also a reference to the song "Do-Re-Mi" from the musical The Sound of Music in the line "When you know the notes to sing, you can sing most anything". The song received generally positive reviews from Music critics, who complimented the song's refreshing dance oriented nature, in contrast to the previous single, the sexually explicit Erotica, and called it one of Madonna's strongest disco-oriented songs.

The music video for "Deeper and Deeper" was directed by Bobby Woods and shot on November 7 and 8, 1992. It was seen as a homage to artist Andy Warhol and his films. It was set in the 1970s and featured Madonna playing a character based on Edie Sedgwick who goes out to a nightclub and finds her friends and boyfriend (played by actor Udo Kier, who had appeared in the Andy Warhol films Flesh for Frankenstein and Blood for Dracula and had previously appeared on her "Erotica" video). The video also features the cameos of gay-porn director Chi Chi LaRue, porn actor Joey Stefano (who had also appeared on Madonna's controversial Sex book), Madonna's good friend an collaborator actress Debi Mazar and film director Sofia Coppola playing the role of Madonna's girlfriends. It also features Warhol regular, Holly Woodlawn. The video itself received mixed reviews from both music critics and fans alike. It's considered one of Madonna's most intriguing yet least appealing music videos. It also marked the first time Madonna appeared in one of her music videos with her eyebrows shaved off. She claimed this was one of "the best things I ever did."

Madonna has performed "Deeper and Deeper" in two of her concert tours. She first performed the song on The Girlie Show World Tour in 1993. This performance, like the song's music video, had a strong disco theme, with Madonna and her back up singers and dancers wearing afro wigs and bell bottom pants. The song was not included on a tour until 11 years later on the Re-Invention World Tour (2004) where, as opposed to the original disco version, it was performed as a slow-cut jazz version, with trumpets and an up-right bass and featuring Madonna dressed as a circus showgirl. It was also rehearsed for Madonna's 2006 Confessions Tour but ultimately was not included.

"Deeper and Deeper" has a legacy, despite the sexual nature of the Erotica album and the controversy surrounding Madonna and the album at that time, "Deeper and Deeper" met with positive reviews and received significant radio and airplay. Critics have called the song, one of Madonna's strongest disco inspired tracks, with her fans calling it one of her best dance tracks. Slant Magazine listed "Deeper and Deeper" as number 36 on the "Best Singles of the '90s" list.