Derek on Being Both a Writer and a Stan
From Madonna's activism to Ethel Cain's storytelling, Derek's picks reflect a listener whose relationship with music is deeply shaped by queer culture, community, and self-expression.
Derek (@derekplease) approaches the June 8 to 12 prompts through a lens shaped as much by pop culture as by music itself. His selections move between soundtrack cuts, iconic album artwork, unrealized music videos, critically acclaimed records, and artists whose work extends beyond the music alone. Across each answer, the music is only one part of a much larger conversation.
The prompts offer a closer look at the many directions those conversations can take. One explores a song that references a drink and opens into a reflection on film soundtracks and sleeper hits. Another focuses on a blue album cover and the turbulent release history behind it. A different prompt turns toward an album track that deserved a music video, while another revisits a beloved album whose reputation is built on its brutal honesty. The final answer examines an album cover that tells a story without words, leading to reflections on his upbringing, faith, and identity.
What’s your favorite song that references a drink?
KatyCats may know the Michigan-born, Los Angeles Valley Girl artist Cyn as pop legend Katy Perry’s first signed artist to Perry’s label UnSub Records. Cyn has appeared on several 2020s pop music-themed soundtrack albums. Like a couple for Pokémon, plus the LP for DC’s Harley Quinn movie Birds of Prey, and twice on Emerald Fennel’s curated LP for her directorial debut Promising Young Woman. Not to mention soundtracks like the animated Smallfoot, and Addison Rae’s Netflix romcom He’s All That. This clever marketing strategy is how I became a fan of Cyn, as I love the Promising Young Woman vinyl soundtrack.
From all those soundtracks, Cyn’s striking song “Drinks” from Promising Young Woman is the most successful, spending two months at US Top 40 Radio in 2020. It peaked at #22 that July. It is a bass-heavy romp written about a night out, one that intentionally excludes your life partner. Because, as to quote Cyn, “he got mad, so I got drinks.”
This simple-yet-biting message makes the song work, but so does its sparse, dark-pop and hip-hop-influenced production. It not only made it onto Promising Young Woman, but onto Netflix’s Inventing Anna, and the HBO Max reboot of Gossip Girl. You’ve probably heard it — and didn’t even realize you were bopping! That’s why it’s my favorite sleeper hit of 2020, and of course my favorite song about a drink.
Which blue album cover do you love?
Prior to its release as Kim Petras’ sexy and succinct, 10-track second studio album in late 2023, Problématique was planned for an earlier release as Kim’s would-be 18-track, COVID-era Euro-dance debut album.
Due to devastatingly widespread internet leaks, the pop album was shelved by Petras’ now-former record label, Republic Records. Republic instead released Feed the Beast — an eclectic and unmistakably commercial album — as trans trailblazer Petras’ debut album. Feed the Beast included Kim’s mega-hit, Grammy-winning collab “Unholy” with fellow queer icon Sam Smith.
As a Kim stan since Era 1, I felt that the best Feed the Beast tracks were the ones originally meant for Problématique. Like the bouncy, viral 2021 single “Coconuts,” the relentless, dark-pop edge of “Revelations,” and the daring catchiness of “Hit It From the Back.” Bops!
Though some Problématique songs were indeed available on Feed the Beast, the visual magic of the Problématique era was still locked up in label jail. Its blue-tinted album cover, captured by the beyond-iconic fashion photog Steven Klein, features Kim nude on a desolate street, clad only in a beret and black gloves. These Parisian accessories are a direct nod to the French house music featured on the LP. An artsy, cursive logo of the album’s title is splashed across Petras’ body in the striking image, perfectly matching the record's catwalk-ready basslines. It evokes midnight-in-Paris vibes.
When Problématique was surprise-released mere months after Feed the Beast, it was sweet vindication for Kim Petras fans like me. Problématique earned its cult classic status in pop by sheer internet demand. My favorite Problématique tracks include the sweet and coy “Je T’Adore,” the galactic dance-pop of “Something About U,” the Rodeo shopping spree of “Treat Me Like A Ho,” and the sassy album closer, “Love Ya Leave Ya.”
What’s an album track you wish had a music video?
As a pioneer of “gay guy music video night” myself — the sacred tradition of queers gathering friends to watch music videos together on a screen — I sure wish more album tracks had music videos. While the name of the activity is antiquated in its specificity, its iconic legacy remains. You might even be at a music video night while reading this.
I used to host music video nights on livestream sites back in the mid-and-late-‘00s, and of course in real life. I remember watching the premiere of Lady Gaga & Beyoncé’s “Telephone” music video on cable, with a living room full of friends — and my mom! “Music… makes the people… come together,” to quote Madonna, the queen of any done-right music video night. And she’s right, the unsung tradition of music video night unites people of all identities.
Truly, any gathering can become a music video night if your taste and selections are just right.
I look back fondly at playing music videos as background noise at parties in my twenties, only for the glow of the TV to attract straight and queer folks alike “like a moth to a flame, burned by the fire,” to quote Janet Jackson, another mother of the music video format. Truly, any gathering can become a music video night if your taste and selections are just right.
To directly answer the question, I wish Madonna’s vision of a Quentin Tarantino-directed music video for her 2012 MDNA album track “Gang Bang” had come to fruition. However, her cinematic and stellar “Gang Bang” live concert performance from MDNA World Tour being immortalized on video more than makes up for Quentin’s loss. Look it up.
Which album deserves every bit of praise it gets?
It’s hard to describe how fresh and revolutionary UK singer-songwriter Lily Allen’s sophomore album It’s Not Me, It’s You sounded to me as an American high school senior in the late 2000s. Even as a lifelong fan of British pop culture, I was not ready for the raw, brutal honesty of the LP’s confessional, blunt lyrics, mixed with state-of-the-art pop production by Los Angeles’ brilliant Greg Kurstin. The production and co-writing by the American Kurstin mixed phenomenally well with Lily’s innately British sensibilities, resulting in one of her most ambitious and beloved projects ever.
Of course, It’s Not Me, It’s You has been Allen’s signature album up until the release of her 2025 LP West End Girl, so most of us are privy to the former’s pop legacy. Still, It’s Not Me, It’s You deserves every bit of its praise for not only inspiring pop music as a genre, but for directly inspiring music of other genres. T-Pain used Allen’s intro vocals from her single “Who’d Have Known” as the hook of his 2011 single “5 O’Clock,” which was Allen’s first top-10 hit on the Billboard Hot 100 in the US, at number 10.
Perhaps the most praiseworthy element of this oft-praised album is its brutal honesty. The “you’re bad in bed” energy of “Not Fair.” The scathing ‘00s pop culture commentary of its iconic lead single “The Fear.” The “I guess I’m old now” melancholy of “22,” written from the aged-out club kid POV of someone approaching the dreaded, self- and societally-imposed “deadline” age of 30.
Brutal honesty is what has made Lily Allen stand out, and until she did it again with West End Girl, It’s Not Me, It’s You was an across-the-pond pop cultural achievement, alongside Kurstin, that only a genuinely genius pop artist like Allen could bare her soul to create.
Which album cover tells a story without words?
While the fictional story behind trailblazing, trans, indie musical artist Ethel Cain’s Preacher’s Daughter has been widely dissected by fans, the emotions the cover art evokes for me are deeply personal. Personally, witnessing Cain delicately posed like a “good Christian” in front of a historically inaccurate, framed portrait of a problematic Caucasian Jesus reminds me of growing up as a queer Catholic at odds with my own faith. Meant to dress and behave a certain way on holidays… and to respect institutions that aren’t always — if ever — respectful back to us queer folks.
The power of this album cover is that it told me a personal story the first time I saw it, which in turn drove me to listen to the actual album and discover its fictional narrative. It opened me up to art I might not have experienced had I not seen my own reflection in its cover art. This proves that not only can visual art sell an album to a listener, but it can do so on a very personal level.
The fuzzy haze of the blown-up Preacher’s Daughter vinyl cover art is also emotionally affecting to me, as it positively reminds me how increasingly fuzzy and distant-feeling my childhood is from my life today. While I am still spiritual, I do not belong to an organized church. I identify as a gender non-conforming male. LGBTQIA+ indie artists like Cain (and also the recently indie-again Kim Petras) remind me that I can carve a lane for myself — and find success on my own terms — in my career as a queer writer.
One of the more interesting things about Derek's answers is how he comfortably moves between both analysis and admiration. He can tell you where a song appeared, the story behind an album’s release, who photographed the cover, or why a particular record mattered within a larger cultural moment. Under all that knowledge, there is still the perspective of someone who genuinely loves the music. The facts are never there to prove expertise, they are there because they are part of what makes being a fan so rewarding in the first place.
That balance shows up throughout his relationship with music. He reads liner notes while listening, collects physical media, and reviews concerts. Whether he's writing about Madonna, Kim Petras, Lily Allen, or an overlooked soundtrack gem, music remains both a subject to explore and something to simply enjoy. Somewhere between being a journalist and a stan, Derek seems perfectly content staying both.
A writer and record collector whose ideal listening session involves a great album, a lyric sheet, and enough time to fall down a few music-history rabbit holes along the way.
