Albums: Erotica (1992), GHV2 - Greatest Hits Volume 2 (2001)
Songwriters: Madonna/Shep Pettibone/Tony Shimkin
Producers: Madonna/Shep Pettibone

“‘Deeper and Deeper,’ from the same album, lowered some of the upturned noses caused by the ‘Erotica’ single. But they were soon raised again when they discovered that the track was about a miner coming to terms with his homosexuality, ‘I can’t help falling in love, I fall deeper and deeper the further I go,’ he sings as he disappears into the dark shaft.”
- Dan Cadan, only slightly joking, from the GHV2 liner notes

Miner metaphors aside, Deeper and Deeper may be Madonna’s single gayest track - or at the very least, her most unabashed attempt at recreating the string-heavy disco sound she was born half a decade too late for. And though it resembles Vogue, even quoting its euphoric final chorus to great effect, it’s not exactly a direct sequel. Instead of falling back on the era’s dominant house beats, Shep Pettibone’s production does what Stuart Price’s would fourteen years later: update disco for the (then-)present.

As perhaps the only overt pop song, and therefore the one truly commercial single on the Erotica album, Deeper and Deeper sounds like a contradiction on paper; what detractors would call a last-ditch sell-out to radio. And yet in classic Madonna fashion, it nails the sense of conflict at the heart of Erotica over one of her most danceable tracks ever, whilst maintaining her artistic vision - she notably insisted on including the flamenco guitar interlude, which, radio be damned, even gets a full, glorious airing on the single edits.

“I can’t help falling in love
I fall deeper and deeper the further I go
Kisses sent from heaven above
They get sweeter and sweeter the more that I know”

Though pop is filled with similarly lovestruck choruses, it’s not hard to see where Deeper and Deeper’s particular gay appeal stems from - it may be about a man she loves, but it deliberately reads like an argument for homosexuality as individual nature, not a choice. Whilst Celebration may have inadvertently summed up Madonna’s entire ethos with “If it feels good, then I say do it”, Deeper and Deeper - evoking Like a Prayer - even suggests God himself endorses homosexuality. Why resist what feels natural, and above all, right?

“Someone said that romance was dead
And I believed it instead of remembering
What my mama told me
Let my father mold me
Then you tried to hold me
You remind me what they said
This feeling inside
I can’t explain
But my love is alive
And I’m never gonna hide it again”

Furthermore, if your parents taught you the values of independence and intuition - “think with your heart, not with your head” - why not take that advice, even if they disapprove of homosexuality? As the song’s tension builds, it takes on an almost I Will Survive-like combination of celebration and determination (minus the camp), whether or not it’s directly about coming out. And though Madonna never quite had the vocal power to truly be one, her final, infinitely triumphant “never gonna hide it again” is one of her greatest diva moments on record.

So Deeper and Deeper was the obvious choice, the reassuringly danceable follow-up single to the controversial Erotica - yet it only peaked at #7 on the Hot 100. Why did such a predestined-sounding hit never quite make it big? Looking at the 1992/93 charts, R&B and ballads dominate - Whitney Houston’s cover of I Will Always Love You spent a mind-boggling 14 weeks at #1 - and the Erotica album was not so blatantly of its time, though it holds up far better than most of the time-stamped music of its era. With Madonna carving out her own, not-entirely-hip musical path, her star power alone was simply not enough (and never again would be), especially with the public backlash against her during the Sex era. It’s telling that in a time where Mariah Carey reigned, Madonna would have to conform to top the charts (albeit while producing excellent music) - the R&B-styled Take a Bow was her second-last ever #1 in 1995.

YouTube / Dailymotion

Director: Bobby Woods

The video for Deeper and Deeper is not so much deliberately uncommercial as totally unconcerned with MTV airplay. Perhaps the bigger problem is that although its treatment is a clear tribute to the ’60s and Andy Warhol, with Madonna as Edie Sedgwick (ironically, without eyebrows), it’s difficult to find any meaning in the visuals, or story in Madonna’s wanderings. There’s something impersonal about the whole affair - Madonna doesn’t lipsync, and barely looks at the camera bar a photoshoot scene - but for once, her makeover doesn’t feel like yet another extension of her personality. Nor is she reincarnating Edie Sedgwick like she did Marilyn Monroe in Material Girl; it feels like another person altogether, someone clearly enjoying herself, but hard to relate to. Seeing her under disco balls doesn’t make us feel like dancing. Nothing wrong with mildly baffling music video treatments that bear no resemblance to their songs (Madonna has many!), but this one just wasn’t compelling enough to work.