My girlfriend Theresa and I are Gen Xers of the same vintage, and we both love The Smiths, particularly epigrammatic sad-bastard demigod Morrissey. Though we see many concerts together, a scheduling quirk meant we recently wound up attending two separate concert dates on Moz’s current tour.

I saw Morrissey’s show at Radio City Music Hall last October, near the start of the tour. Theresa caught him three months later at the Brooklyn Academy of Music—just a couple of weeks before the 53-year-old Pope of Mope announced the postponement of several tour dates due to, appropriately enough, a bleeding ulcer.

Notwithstanding this encroaching ailment, the Brooklyn show Theresa caught in January was widely agreed to be the best among Morrissey’s New York City dates. For one thing, he was in a rare good mood—delighted to be making his Brooklyn debut and remarking upon it several times from the stage. For another, Moz had improved his set list since I saw him in October, selecting better solo cuts (“November Spawned a Monster”) and swapping in crowd-pleasing Smiths chestnuts like “How Soon Is Now?” and—critically, from Theresa’s perspective—”Please, Please, Please Let Me Get What I Want.”

“That was the first Smiths song I ever heard,” Theresa gushed, recounting her shocked delight at hearing the baroque, mandolin-inflected ballad. “Reminded me of being 14 and hearing it in my mom’s car after I bought the Pretty in Pink soundtrack cassette.”

“Me too, come to think of it,” I replied, jealous. I’m almost positive “Please, Please” was the first Smiths song I ever heard. And it was undoubtedly the first Smiths song I ever owned—on that same soundtracks.

Our conversation inspired me to pull my dusty Pretty in Pink CD off the shelf and reminisce about the spring of 1986. This act of nostalgia didn’t just make me wistful. Thinking about all that happened in music in the half decade that followed, I actually felt regretful for Morrissey, guitarist Johnny Marr and the rest of the band.

I came to the belated conclusion that the biggest mistake The Smiths ever made wasn’t breaking up; given how much the foursome came to loathe each other, that was inevitable. It was breaking up in 1987, because John Hughes almost made them rock gods.

The pioneering work of Hughes, the teen-sympathetic filmmaker who helped define the 1980s, has been well-chronicled by my fellow Gen X critics and needn’t be recounted again. There have also been encomiums written about his ear for and smart use of music in his films. In 2009, on the occasion of Hughes’s death at age 59, the 1985 Simple Minds song “Don’t You (Forget About Me),” from his movie The Breakfast Club, soundtracked many a tribute.

Somewhat less remarked is how pivotal Hughes was in helping to break what became known as alternative rock in America—he served as a bridge between what was known in the first half of the ’80s as postpunk or new wave and what would be called alt-rock or indie rock by the ’90s.

Pretty in Pink, named for the Psychedelic Furs’ new wave classic, was the third chapter in the Hughes–penned and -produced triptych of Molly Ringwald films and the first not directed by him (the workmanlike Howard Deutch handled it). It’s arguably the weakest of those films, though it has its partisans. What’s inarguable is that its soundtrack had a longer shelf life than the film.

The Pink soundtrack was released in the winter of 1986, just ahead of the movie, and by spring it was a Top Five, gold-selling album; it rode the charts for more than half a year. To a large extent, the album’s strong sales were the result of its biggest hit, Orchestral Manoeuvres in the Dark’s gushy, lovelorn “If You Leave” (No. 4, 1986). But OMD’s hit doesn’t entirely explain the soundtrack’s success.

Hughes’s classic teen films weren’t automatic hit-album generators. In 1984, Sixteen Candles spawned a five-song soundtrack EP; it left out virtually all of the film’s best songs and didn’t chart. The soundtrack to The Breakfast Club only scraped the Billboard Top 20 despite having Simple Minds’ chart-topping smash on it; it eventually went gold, but the bulk of the disc consisted of instrumental score.

The Hughes-directed 1986 summer blockbuster Ferris Bueller’s Day Off had no soundtrack. Hughes declined offers to put one together, and the film’s biggest “hit” was the Beatles’ classic cover of “Twist and Shout.” It hit the charts again (No. 2, 1964; No. 23, 1986) but, as a song by the biggest band ever, couldn’t be licensed for a soundtrack.

What made Pink unique wasn’t the fact that the film was music-inspired and named after a rock song; so was Sixteen Candles. It wasn’t spawning a big pop hit; Hughes’s Breakfast Club had done that, too. Rather, Pretty in Pink, the album, was singular for being coherent, forward-looking and sui generis, something more than a movie keepsake. [...]