The 50 Best Pop Singles Of 1994 (Featuring New Interviews With Ace Of Base, TLC, Lisa Loeb, Real McCoy & Haddaway)

3. LISA LOEB & NINE STORIES, “STAY (I MISSED YOU)”

The glasses. Everybody remembers the glasses. But it’s also that fragile, tentative guitar. And Lisa Loeb alone in a loft, singing directly to you. Smart, sincere, sensitive — too much so for its own good — “Stay (I Missed You)” is the quivering, questioning heart of Generation X…and of anyone else who hears it.

No one is immune to the evergreen charm of “Stay (I Missed You).” Not then, not now, not even the inmates of Orange Is The New Black, whose impromptu sing-a-long of her song last season delighted Loeb to no end.

“When you see these prisoners singing this love song, or the fact that so many different women from all walks of life knew all the words, there was a humor in that,” she says. “But at the same time it was very earnest and touching. It captured the magic of what it feels like to have a hit song: seeing people connected by music.”

In 1994, Lisa Loeb was an Ivy League grad who temped by day. At night, she played the NYC club and coffeehouse circuit, armed with a purple cassette’s worth of self-penned material, a backup band named after a J.D. Salinger collection and her soon-to-be-iconic cat’s-eye glasses (which you can now buy, via her own line!). As part of a collective of young up-and-coming artists, she would also perform songs — including “Stay (I Missed You)” — during set changes of her friend Ethan Hawke’s theatrical shows.

He returned the favor by recommending her to Ben Stiller, which helped Loeb and “Stay (I Missed You)” grab a slot on the soundtrack to the film Reality Bites. Hawke went one step further, coming up with a revolutionary music video concept. His plan? To direct a one-take clip featuring Loeb singing alone. (With a cameo from his cat Mardot.)

“For me, as somebody who loves games and puzzles, it was a good challenge,” Loeb remembers. “Ethan told me about the idea in his kitchen, and he paced out the choreography, or what the loose story of what it was, because there’s a relationship between me and the camera.”

Although performance scenes with Nine Stories were filmed, the one-take, one-performer concept proved too powerful to pass up, despite Loeb’s initial misgivings of appearing without her guitar or band.

“I didn’t want to be misperceived as a pop singer. I wanted people to know that I actually played the guitar and that, when they hear the song, it’s a full band. But in the end, the concept of the video was too good not to do,” Loeb says. “Back then, highly produced, highly glamorous videos were so popular. And this was so different, which was great because it showcased how the music was different.”

Without a record label, Loeb didn’t expect for her song to become the major single off the Reality Bites soundtrack, but a radio station in Houston liked it so much they began playing it, which led to other stations across the country picking it up. To everyone’s surprise, “Stay (I Missed You)” topped the Billboard Hot 100 for three weeks, making Loeb the first unsigned artist to hit #1 — a feat not duplicated until Macklemore & Ryan Lewis took “Thrift Shop” to the top in 2013.

“I think part of the reason that the song gained popularity was the contrast to what else was on the radio at the time. It has such an intimacy,” Loeb says. “That’s always a reminder to me when I’m writing and recording music now. The songs that connect best are the ones that just come through you: the ones you craft but don’t overdo.”

Grammy-nominated, “Stay (I Missed You)” landed Loeb a million-dollar record deal and helped usher in the late 1990s era of Lilith Fair, where instrument-playing women were celebrated for their songcraft more than for their sex appeal. In the years since, Loeb has branched out into acting and voiceover work, but she never stopped adding to her musical success. Not only is her ninth studio album, 2013’s No Fairy Tale, a must-listen — the cut “The 90s” references her “Stay (I Missed You)” experience — but she’s putting the finishing touches on songs for a musical, Camp Kappewanna, that will be produced by New York City’s Atlantic Theater Company in Spring 2015.

Although Loebian lyric-and-guitar-driven vulnerability is in short supply on today’s increasingly glossy, overproduced charts, her influence can be felt everywhere from Beyoncé’s “Irreplaceable” to Ingrid Michaelson’s bespectacled sleeper success. Without a doubt, however, her greatest disciple is Taylor Swift, who covered “Stay (I Missed You)” during her 2011 Speak Now Tour and continues to champion the Lisa Loeb school of self-composed, quietly courageous singer/songwriters.

As magical as Swift can be, however, time will tell if she can capture a moment of her own that is as instantly and effortlessly evocative and timeless as Loeb did with “Stay (I Missed You).” What is it about that song that makes it immortal: as young and fresh forever as if it’s still 1994? Whether you’re hearing it for the first time or the five-hundredth, how is it still able to make even the most jaded among us remember our very best and most beautiful selves, even for just a second?

Maybe it’s Lisa Loeb alone in a loft, singing directly to you. Or that fragile, tentative guitar. Or the glasses. Everybody remembers the glasses. — JONATHAN RIGGS