The final season of The Sopranos is casting a long shadow in my life these days. I know, this is a music site—we’ll get to that. But as I write this, there are merely two episodes left in the greatest television show ever, and I’m pretty deeply engrossed. Anyone familiar with the show knows that music has always played a huge role, and after a recent episode used Van Morrison’s cover of “Comfortably Numb” to set-up maybe the series’ most singularly breathtaking moment, I was ready to dig deep into why the song choice was absolute perfection…

…until I discovered that those crafty Sopranos-deconstructors at Slate beat me to it. (And did a far better job than I ever would have; I mean, the guy brings Hitler’s secret bunker into his analysis—no way I would’ve dug that deep.) But it led me to ask: what is my favorite moment of pop song/TV show symbiosis?

I could easily come up with a list of about two dozen moments. So I promise that: a) I won’t list all of them here, and b) I’ll continue to revisit this topic in the future—and likely have many arguments with myself. Where then, do I begin?

I begin with Dana’s panties, although you’ll have to stick around for the details. I’d considered beginning other places. Miami Vice’s dark, pastel moments would have been good place to start. Specifically Vice’s signature moment: Phil Collins’ “In the Air Tonight” playing numbly beneath the scenes of Crockett and Tubbs speeding desperately through the streets of late-night Miami. I also thought about beginning with David Lynch’s Twin Peaks—those super-freaky sequences that combined Julee Cruise’s ghostly, nightingale voice, and the inexplicably harrowing images of a red curtain.

And Dana’s panties were almost trumped by my memory of listening to the theme from M*A*S*H, “Suicide is Painless,” play at the end of that final episode as Hawkeye’s helicopter rises into the sky above B.J.’s stone-spelled “Goodbye.” I was 12 when it first aired and had to go to bed before the episode ended, but we had just gotten the coolest thing ever: a VHS recorder. So I taped the last hour and woke up at 4:30 a.m. to watch it in the dark before school. It was near dawn when the song started playing—this eerie, dreamy instrumental theme that echoed back to my earliest memories of TV: hidden in the kitchen shadows after sneaking out of bed, catching glimpses of army green canvas in a scrubby landscape while my parents laughed at things that didn’t actually seem funny, but were nonetheless captivating in their otherworldly feeling of adult cleverness. So when that song played in those early morning hours as I watched the characters say goodbye, the whole world froze for a moment in a state of ideal melancholy. Whenever I hear that song now, the moment comes right back—perfectly permafrozen, just as fresh as the first time I saw it. Nonetheless, that isn’t what leapt to mind when I asked: what is my favorite moment of pop song/TV show symbiosis?

No, when I asked myself the question, the first two words that popped into mind weren’t Miami Vice, Twin Peaks, or Goodbye Hawkeye, they were: Dana’s panties. The song was “She Will Have Her Way” by hook-master Neil Finn. The show was Aaron Sorkin’s Sports Night, a behind-the-scenes series about producing a nightly sportscast—an underdog version of ESPN. Sports Night, which ran from 1998–2000, falls into that “love/hate” category. For some, Sorkin’s trademark walk-and-talk banter and his affection for scripting the “big moment” is just too much. For others, like myself, there is nothing quite like the giddy, rhythmic, literate pleasures of the heavily-allusive dialogue that is the heart of Sorkin’s writing. Finn can arouse a similar conflict: some feel they’re being manipulated by a hook-heavy huckster, while others, like myself, are happy to soak in his gorgeous, melodic, pop-song craftsmanship.

Most of all, they’re both Romantics—in the literary sense, not the Harlequin novel sense. They both love that big romantic moment—the epiphany, the transcendent, ephemeral instant of intense being—and showcase it in their work. When they hit their mark, their best creations can induce that buzzy endorphin-rush that pop songs and pop TV specialize in. And when they hit their mark together, at the same time, they created a truly sublime moment of pop song/TV show symbiosis. This moment of mutually-timed pleasure might be the apex in a certain sexual analogy, one that I’m far too shy and Midwestern to reference here. Which brings me back to Dana’s panties.

In a scene (from a season 2 episode, “Louise Revisited”) that is far less salacious than you are probably imagining, a pair of black panties are pulled from a desk drawer at the exact moment that “She Will Have Her Way” begins to play. The panties are not evidence of anything that has happened, but a suggestion of what might be possible. The moment is a devious, blood-pumping culmination of a long-simmering, open flirtation between two characters who were the heart of the series: Dana (Felicity Huffman) and Casey (Peter Krause). It was Huffman and Krause before her Oscar nomination and his star-turn in Six Feet Under, but their charisma was obvious on Sports Night. It was Sorkin before West Wing, and he was absolutely bringing it with every episode he wrote for Sports Night’s two glorious seasons. It was Finn after Crowded House, solo for the first time, and making me swoon again with the delirious “She Will Have Her Way.” And together they authored the perfect pop music/TV moment.

The moment is, of course, best consumed in its native setting, after having experienced a full season of Dana/Casey advances and retreats. I hesitate to even include the out-of-context YouTube clip, because it simply doesn’t do it justice (and it cuts off the very end of the scene). But it’s my duty to bring these things to you. And I’m nothing if not your dutiful pop culture half-Filipino house boy. So here, at last, are Dana’s panties:

Michael Jordan? Total freak. Absurdly mutant-like muscular control combined with freakish creative spatial analysis abilities. He won the genetic lottery and got to test-drive the prototype genes. In 10,000 years, all of us will dunk like Jordan.

And everyone will make music like Prince.

The Purple One is a true freak—few musicians seem to more frequently elicit that description from fellow artists. When asked about his legendary productivity or live virtuosity, musicians tend to roll their eyes and mutter something like: “Well, yeah, but that’s just Prince. He’s a freak.”

A funny thing can happen on the way to freak-hood—you can discover that great ability doesn’t always lead to great art. For all of his virtuosity, Prince’s recording career has been a wild and sometimes frustrating ride, artistically speaking. As a live performer, he’s as vibrant and amazing as ever. In fact, since he’s grown up and tamed his ego in the last two decades, he’s transformed into a masterful, generous band leader, and his late-night, small-venue shows are tight, funky, and explosive.

On stage, old Prince might actually kick young Prince’s bikini-briefs-clad ass. In the studio, however, young Prince was a mad little alchemist with his finger on the pulse of everything funky, and he got his freak going at a level that old Prince hasn’t been able to muster. At his best, he was much more than just funky—he was filthy, sexy, sweet, crooning, rocking, thumping, aching, piercing, stirring, and, on occasion, devastating (which, ironically, most often seemed to occur in his smallest gestures—like the almost carelessly knifing guitar licks that slice through the ending of the title song from Sign ‘O’ the Times, but we’re getting a little ahead ourselves).

Today, sadly, when you call Prince a freak, most people think you’re referring to his series of name changes and various religious transformations. But this Spring is a time to remember the freak that was, a time to celebrate the 20th anniversary of the release of the album that is—at least to most true Prince-o-philes—The Purple One’s Sistine Chapel: Sign ‘O’ the Times.

Sign is his great monument to freakishness, a double-album solo venture in which he plays nearly every instrument, makes almost every sound, and gives it the full-on Prince-alone-in-the-studio treatment. He was in what I think of as his “Mozart” period—the celebrated, bawdy, man-child virtuoso playing to an attentive continent, buzzing from a string of popular and critical successes, at full confidence and the height of his powers.

Prince was a writing and recording tornado in the mid-80s preceding the 1987 release of Sign. Legend has it that he was working on a triple album opus titled Crystal Ball (which popped up in various bootleg forms and eventually became the title of a vault-clearing set of CDs released in the late 90s) that was nixed by the studio for its length—just the beginning of Prince’s long battle with Warner Bros. regarding his over-saturation of the market. So Crystal Ball went underground, and Sign was born.

It was his first album after disbanding The Revolution, and it followed two albums (Around the World in a Day and Parade) that were brilliant, but nonetheless felt like distinct stylistic statements instead of fully-realized artistic visions. You could hear Prince looking for himself, for the next thing after Purple Rain. On Sign ‘O’ the Times he found what he was after.

Sign was a new Prince. Somewhere between the narcissistic (though often gorgeous) Euro-melodrama of Parade and the first spare, haunting, drum-machine beats of Sign’s title track, the boy became a man. Exhibit A might be the album’s take on love. Prince could always sing about sex, but love was another matter. Sign is the first album on which he seems to understand that love actually can be better than sex, and the results are intoxicating. Nowhere else does Prince reach the romantic heights that he does on the ballads “Slow Love” and “Adore.” The latter, which is the album’s final track and features his crushing falsetto vocals, simply is the ecstasy of falling in love, down to the last hormone. In fact, the slow-burn musical orgasm that concludes “Adore” is the best finish of any Prince album—its final peaking chord echoing like some heavenly chorus ringing in his own Sistine Chapel.

You need more convincing? I see, you just want to hear me gush some more. All right, then. Here are just a smattering of other reasons why you should be hitting PLAY on the Purple One’s wicked masterpiece right now:

• Because, my God man, did you hear me—he writes, arranges, plays, and mixes virtually every instrument, voice and sound on the damn thing! And he plays the hell out of it all. It really is that most overused of musical compliments: “a one-man tour de force.” (With the notable exceptions of longtime collaborator Eric Leeds on sax and Atlanta Bliss on trumpet.)
• Because the title track “Sign ‘O’ the Times” absolutely kills with its stripped-down, understated dread, stark beat, and intensely restrained slashes of guitar. And that the socially-pointed lyrics still seem to speak directly to today’s problems is either prescient or just outright depressing. Prince was rarely much of a political/social lyricist, but for four minutes at the beginning of Sign he sounds convincingly like his musical Minnesotan brother, that Robert Zimmerman guy.
• Because “Play in The Sunshine” is pure jamming joy, with little streaks of screaming electric that are almost camouflaged among the song’s cacophonous jungle.
• Because when the needle scratches off the record and he hollers, “Shut up already, damn!” to begin “Housequake,” you do exactly as he says, and then you dance. And because every time he struts through that moment near the song’s end, slyly uttering “Shock-a-lock-a-boom. What was that? Aftershock,” you just gotta shake your head with him.
• Because it’s possible that nothing in Prince’s entire catalog has aged as well as woozy, slippery gem “The Ballad of Dorothy Parker.” It’s the album’s shot of 24-year single malt—slow-smoked, jazzy funk sliding beneath a dirty literary dream sequence that reaches its apex with a sublime Joni Mitchell allusion.
• Because “It” just makes you feel like having sex. And because “Hot Thing” makes you want to rub up against sexy strangers (and reminds you that Prince has always known how to pick a sax player).
• Because the bright piano chords and swooshing drum-machine of “Starfish and Coffee” are like candy. And because its follow-up, “Slow Love,” is like slipping into a steaming, candle-lit bubble bath after having your candy. (Oh, don’t be so macho—you know you’d love a steaming, candle-lit bubble bath.)
• Because “Forever In My Life” is so goddamn beautiful and achingly simple.
• Because despite its straight-outta-the-80s glam feel, “U Got the Look” reminds you one more time that the Diminutive One can play that guitar.
• Because the subtle, complex, gender-bending “If I Was Your Girlfriend” keeps on haunting you long after its off-beat groove has ended.
• Because “Strange Relationship” makes you want to pick up a tambourine.
• Because if you listen carefully, “I Could Never Take the Place of Your Man” will absolutely break your heart. And when those simple, happy/melancholy riffs finally lead into an extended meandering guitar line during the song’s closing jam, you can feel him tracing the crevices of that delicate fault-line along which a heart breaks.
• Because “The Cross” is just a freak, his guitar, and a trap set.
• Because the chaotic exuberance of the live-from-Paris “It’s Gonna Be a Beautiful Night” is a glorious 9-minute celebration of existence.
• Because that slow-burn musical orgasm, “Adore,” is simply ethereal.

So, go forth and Prince-ify! Then return and testify! Feed your inner freak. How does your Sign sound 20 years later?