Happy 20th Anniversary to Amy Winehouse’s debut album Frank, originally released October 20, 2003.
About five years ago, Mitch Winehouse, father of singer Amy Winehouse, announced that his daughter was going on a world tour. That would normally be unsettling, considering that she’d been deceased for nearly a decade. But what Mitch had in mind is a concert tour featuring a hologram of the iconic singer. The shows would have a live band playing her songs and one of those elaborated conceived and executed holograms “singing” obviously pre-recorded vocals for the audience to enjoy.
Naturally, the announcement didn’t go over particularly well. It was seen as a publicity grab by a father who both used and enabled his troubled daughter in life, and was now searching for further ways to cash in after her death.
Plans for the tour were quietly scuttled a few months later. With the rise in usage of AI over the past few years, I’m a little surprised that the elder Winehouse hasn’t revived the idea. But no matter what, a fake Amy Winehouse performing “live” in concert seems particularly sacrilegious. She was, for lack of a better term, just too fucking real.
Amy Winehouse was a young, Jewish, streetwise woman from North London, and her music reflected it. She had grown up on Frank Sinatra, Tony Bennett, Sarah Vaughn, and Dinah Washington, but the persona she created for her own material was completely unvarnished. Her first album Frank, released 20 years ago in the United Kingdom, reflects this approach.
Amy Winehouse was a once in a lifetime talent, an absolute rarity of artist who seemed to be great at everything. She was a gifted songwriter with a powerfully distinctive voice, singing ability, and dominating presence. She was a solid guitar player, with an encyclopedic knowledge of many genres of music, especially jazz. Making things even more amazing was that she was only 20 at the time of Frank’s release.
Frank is very much a jazz album. It’s Winehouse’s response to what she perceived as the phoniness of the UK’s pop music scene during the early 2000s, which she thought was populated by talentless airheads. Winehouse prided herself on her songwriting ability, and as a songwriter, she was wise beyond her years, while still every bit a coarse 20-year-old woman.
Like much of her United States-based audience, I didn’t hear Frank until after the smashing success of her sophomore album Back to Black (2006). Back to Black had made her a mega-star, so I was interested in exploring her beginnings. I scooped up Frank when it was re-issued stateside and marveled at the way she seems to personify a seasoned jazz vocalist.
And, truth be told, I was a bit surprised when I really delved into the lyrics. Winehouse pulled no punches when it came to the subject matter of her songs. She spoke about pain, rejection, love, lust, and betrayal, but she did so with a bluntness not found among traditional jazz vocalists. It was simultaneously refreshing and a little off-putting, until I set aside my pre-conceptions and recognized that, yes, 20-year-old women can be skanless too.
Much of the album’s production is handled by Salaam Remi, a New York-born producer at the time best known for his collaborations with hip-hop and dancehall artists. Though he’d produced tracks for rappers and groups like Craig G, Da Bush Babees, and Zhigge, he really made his name producing a pair of remixes for the Fugees (“Nappy Head” and “Vocab”) that set the stage for the group’s “rebirth” with The Score (1996). He’d also produced for such reggae dancehall luminaries as Shabba Ranks, Patra, and Bobby Konders, and was best known for working behind the boards on Ini Kamoze’s “Here Comes the Hot Stepper.”
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By the early 2000s, Remi had begun re-establishing himself through his production for Nas. He’d met Winehouse soon afterwards and began a musical partnership that would last the rest of her career. His production meshed well with her more “hip-hop” sensibilities, even though the soundscape that they created was very much steeped in jazz traditionalism.
Much of Frank’s subject matter seems to deal with Winehouse’s break-up with her boyfriend at the time, Chris Taylor. It’s a bit hard to know for sure, because Winehouse was relatively private about the meaning of her songs. “Stronger Than Me,” the album’s lead-off track and first single, is a harsh kiss-off song dedicated to “someone” she had recently been in a relationship with. The musical backdrop, led by Winehouse playing her guitar along a programmed drum track and accompanied by a full horn section on the chorus, belies a deep sea of bitterness and anger.
Winehouse, who co-wrote the song with Remi, remains insistent that she needs her man to take the lead in their relationship, something she insists was lacking with the nameless someone who is probably Taylor. She gets downright mean, questioning both the former boyfriend’s masculinity and sexuality, deriding him as a “lady boy” and mocking him for not “liv[ing] up to his role.” Two decades later, it’s toxicity is extremely off-putting, but it certainly set the tone for the album.
“You Sent Me Flying,” another of the album’s singles, also deals with her break-up with someone who could well be Taylor. Here she reflects on her ex unceremoniously dumping her due to their difference in age. (“You Sent My Flying” = you kicked me to the curb). She wrestles with her mixed emotions throughout the song with an amazing amount of depth, measuring her feelings of rejection with her own deep feelings about the person she seemed to love. She sings, “And although he's nothing in the scheme of my years / It just serves to bludgeon my futile tears / And I'm not use to this, I observe, I don't chase / But now I'm stuck with consequences, thrust in my face.” Much of the song features Winehouse singing over a melody played by a lone piano, with Remi dropping the famous “Hihache” drum-break by the Lafayette Afro Rock Band (best known for its usage on Biz Markie’s “Nobody Beats the Biz”) about halfway through.
“In My Bed,” the album’s second single, is one of Frank’s more interesting compositions. Remi re-uses the “Apache”-sampling beat he created for Nas’ hit “Made You Look,” adding in a full horn section to enhance the track’s majesty. For her part, Winehouse sings to an ex-boyfriend that she is now content in only using him for sexual release. She sings in her typically candid fashion, “Now it’s not hard to understand why we just speak at night / The only time I hold your hand is to get the angle right.”
Winehouse’s “I don’t give a fuck” attitude permeates Frank, often manifesting itself in the form of dark humor. On “Fuck Me Pumps,” the album’s fourth single, Winehouse lampoons scenester women who seem to flood London clubs in search of rich men to begin a relationship with, only to end up in a parade of one-night stands. Winehouse is completely brazen about cheating on her boyfriend on “I Heard Love Is Blind,” the most laid-back, lackadaisical song about unapologetic infidelity that I’ve ever heard. She attempts to downplay her infidelities with another man who looks suspiciously like her partner by telling him, “I can't even remember his name, why’re you so upset? / Baby, you weren’t there, and I was thinking of you when I came” and “I pretended he was you / You wouldn’t want me to be lonely.”
But she is also able to shift gears as a songwriter, effortlessly switching from wry humor to deep self-reflection. On “Take the Box,” she wrestles with feelings of anger and regret as she ends her relationship with her ex. On the deep and complex “What Is It About Men?” she ponders her own self-destructive nature in trying to form relationships that are doomed to fail, or worse, making all the same mistakes that her father made before. She laments, “I just wanna do my thing / And I'll take the wrong man as naturally as I sing / And I'll save my tears for uncovering my fears / Our behavioral patterns that stick over the years.”
Winehouse also does an excellent job infusing a few jazz standards with her own flavor. She lends her unique vocal tones to a reasonably straight-laced cover of “Moody’s Mood For Love,” best known for its version by King Pleasure during the 1950s, which itself was an adaptation of James Moody’s cover “I’m In the Mood For Love.” Winehouse uses her song to showcase her vocal range and nimbleness, as she dances through the phrases with ease, backed by a saxophone and echoing percussion.
She follows this up with an understated cover of “(There Is) No Greater Love,” a jazz standard originally composed by Isham Jones and Marty Symes, but also performed by the likes of Billie Holiday, Miles Davis, Nat King Cole, Aretha Franklin, and Etta James. Like many of these iconic artists, Winehouse performs it as a ballad, backed notably by a soft guitar, a flute, keys, and occasional sax riffs. Winehouse gets really creative with her reinterpretation of “Mister Magic,” one of the album’s two bonus tracks. She creates a vocalized version of the instrumental opus by famed saxophonist Grover Washington, transforming the jazz-funk track into a dedication for her love of marijuana.
“Amy, Amy, Amy” features Winehouse at her most sultry. The track practically oozes sex, as she describes her effort to seduce the object of her desire, so thoroughly distracted that she can barely complete writing the song. Musically, the song is dominated by a buoyant bassline and slinky muted trumpet track and is arguably the funkiest entry on the album. Paralyzed with lust, she croons, “From the picture my mind drew, I know I'd look good on you.”
Everything completely changed for Winehouse after Frank, both for the better and the worse. She moved to the Camden Town neighborhood of London, where she met Blake Fielder, her future husband and an extremely shady character. By 2006, she’d recorded and released Back to Black, which earned her the fame she completely deserved, but was also completely not ready to deal with.
Even as Back to Black sold millions of copies and turned her into a household name, she was spiraling out of control. She contended with addictions to alcohol, heroin, cocaine, and crack, as well as dealing with crippling eating disorders. She tragically died in 2011, at the age of 27, due to the ravages of her vices and diseases.
Frank is a fascinating look into the musical life of an artist with a wealth of talent who was just discovering how great she could be. It would have been interesting to see if she would have eventually returned to her jazz “roots” as her career progressed. By all accounts, she was talking about forming a jazz/rap group with The Roots’ Questlove, Yasiin Bey/Mos Def, and Raphael Saadiq, and was planning a new solo album with producers Remi and Mark Ronson (who co-produced Back to Black).
Of course, it’s all speculation now, as Winehouse is gone far, far too early. But with Frank, we’re left with a stunning portrait of a woman who could have had it all.
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Editor's note: this anniversary tribute was originally published in 2018 and has since been edited for accuracy and timeliness.