It’s been 25 years since Lisa Loeb carved out a little slice of music history when “Stay (I Missed You)” made its way to No. 1 on Billboard’s Hot 100, an accomplishment no other unsigned act had ever managed.

And she owes it all to things not going quite the way she planned.

The song was written with a different vocalist in mind.

She’d heard that Daryl Hall was looking for material.

“About halfway through writing the song,” she says, “I found out Daryl Hall wasn’t looking for songs anymore. I’m not sure if my lead was even strong in retrospect. But it did inspire me to kind of think outside the box. I get inspired by a lot of different types of things. And I am a huge Hall & Oates fan, especially some of their older songs. So it was a good place to start and a good sort of musical bed to tell a story.”

On the road to ‘Reality Bites’

The next missed opportunity that put her on the path to No. 1 was when her friend and neighbor, Ethan Hawke, asked her to write a song for Ben Stiller’s “Reality Bites.”

“In the movie, he’s in a band,” she says. “And he performs a song called ‘I’m Nuthin’.’ So he asked if I could write a song called ‘I’m Nuthin.’’ A couple of other professional musicians were asked to write a song.

They ended up going with David Baerwald’s version over Loeb’s.

“But Ethan still thought that some of my music would fit in really well with the movie and what they were doing,” Loeb recalls. “And ‘Stay (I Missed You)’ was one of the standout songs that people would always request when I played and Ethan really liked it. So he wanted to pass that along. I don’t know if we sent other songs along with that one. Maybe. I had done so much recording as part of a demo deal with a record label.”

In addition to earning a spot in “Reality Bites,” “Stay (I Missed You)” was chosen to be the first single released from the soundtrack.

What made ‘Stay (I Missed You)’ work

Loeb figures part of what made her breakthrough single so successful is that it offers “a very personal take on a classic heartbreak and argument theme, so people really connect with it.”

It doesn’t hurt that the singer delivers her personal take on relationship troubles in the context of one of the decade’s more contagious ballads or that Hawke directed such a memorable music video. 

“He wanted something that was like me telling a story, singing straight to the camera like I was having a conversation or an argument with someone and that’s what he captured in that one-take video,” Loeb recalls. “I wasn’t even playing my guitar. I was just singing to the camera. And that was such a different type of video at the time that it stood out on MTV and VH1.”

Ethan Hawke and the proximity effect

She met Hawke through a friend she made while a student at Brown University.

“One of my friends at Brown was a professional actor and had been in a movie with Ethan called ‘Alive,'” she says. “So when I got to New York, we ended up running in the same circles. There was a big group of us who were musicians and playwrights and actors, just a bunch of different types of creative people. And we all supported each other and went to see each other play and were involved in each other’s projects.”

She and Hawke were also neighbors.

“That proximity effect is great,” she says, “when you can just go across the street and say, ‘Hey, do you want to go do this or that?’ And we just hit it off. There was a group of us that used to all hang out together.”

Asked if she could tell she’d come up with a special song when she wrote “Stay (I Missed You),” Loeb says, “No, not really.”

Then, she laughs.

“It’s funny. I can never tell if people are gonna like one song more than another. Sometimes it surprises me, some of the songs that people like more. And then, songs that I might work on more and think are better songs, people don’t connect with as much.”

Blasting into the future with ‘Stay’

Those were exciting times for Loeb. 

“I suddenly felt like I didn’t have to continue to do temp work or find other jobs,” she says. “This was blasting off into the future. Especially because the song was on pop radio. It was a feeling of, like, ‘Wow, a lot of people are connecting with this. I think this can be my real job. I can’t wait to see what’s coming next.'”

It also made her feel more confident, which can be important when you’re dealing with a major label.

“I was lucky that I had a song on the radio that we had made the way we wanted on our own,” she says. “I think that gave me a sense of security and also power. Because the record company, to a certain extent, had to say ‘Wait, she knows what she’s doing. She made this herself. And it’s working on radio.'”

Following through with ‘Do You Sleep?’

She followed through on the success of “Stay (I Missed You)” with a second hit that rocked a good deal harder than her breakthrough, “Do You Sleep?”

“We produced that song a little bit more rock,” Loeb says. “That’s the kind of music I enjoy listening to. But then also textural things like the Sundays or Johnny Marr guitar solos. We were just using a sonic palette that really ranged.”

Both songs were featured on her breakthrough album, “Tails,” released in 1995 and featuring her band, Nine Stories.

When Loeb turned in the full-length followup to “Tails,” she says, the label sent her back to write a hit. And she responded with “I Do,” a hit about the label telling her they didn’t hear a hit. 

“I thought the record was already done,” she recalls, with a laugh. “I felt like I was in an episode of ‘Behind the Music’ on VH1 where then the band was made to go write singles. So I wrote a song to the record company, saying ‘You don’t hear it, but I do,’ which was like, ‘You don’t hear a single, but I do.’ It was very literal, and it became very popular.”

One thing that song has in common with her breakthrough, Loeb says, is that it’s completely earnest. 

 “It might not be a love song,” she says. “But there is definitely earnest straightforward emotion in that song.”

Recording children’s music for all ages

Loeb’s career took an interesting turn in 2003 when she released her first of several children’s albums, “Catch the Moon,” which found her reuniting with her pre-fame singing partner, Elizabeth Mitchell of Liz and Lisa.

“It was weirdly less about kids and more about myself and my relationship to what I loved as a kid,” she says. “I loved ‘Sesame Street’ and ‘Mister Rogers’ Neighborhood’ and ‘Happy Days’ and … I loved ‘Free to Be You and Me.’ But I asked my friend Liz to help me make the record because she had already gotten into making a lot of kids music. And the kind of record I wanted to make was real authentic music for all people and she really helped me to capture that.”

In 2017, she released an album called “Lullaby Girl” that took the idea of making children’s records grown-ups could enjoy in an intriguing new direction, an album of “lullabies” that range from “Dream a Little Dream” to “Be My Baby” and “Tomorrow.”

“We started to piece together songs that had titles that sounded like they’d be on a lullaby record,” Loeb explains, “like ‘Be My Baby’ or ‘In My Room’ or ‘The Sun’ll Come Out Tomorrow.’ And Larry (Goldings) and I had had played around with jazz arrangements in the past. So we sort of took that concept to the lullaby record. It really could be in the standards bin at the record store more than with the children’s records, I think. But again, it goes back to that when I was a kid, where entertainment wasn’t divided up between what’s for kids and what’s for grown-ups. It was just music for people.”

Saluting the ’90s with a playful wink

Her latest rock album, “No Fairy Tale,” was recorded with Chad Gilbert of New Found Glory and includes a playfully sardonic look back on an age she helped define with “Stay (I Missed You)” called “The 90’s.”

“Those were the ’90s,” she sings. “And times flies so fast / You say you love me then / But I don’t wanna go back.”

“Chad was like ‘You should write a song about the ’90s’ because that was probably his childhood,” she says.

“At first, I didn’t know what to write because it just wasn’t that interesting from my point of view. Sometimes we don’t associate as much with the eras that we’re known for or whatever. But after a while, I realized that it could be fun to write about the ’90s that I’m associated with. My own songs, MTV. I really wrote about my own experience, making that music. And also respecting that I know I’m very nostalgic for music I grew up with and I understand that people are nostalgic for music that I wrote that they listened to when they were growing up. So I wanted to write a song that appreciates it but still making the statement that I’m moving forward. I don’t forget the past. I hang onto the past. But I also like to move forward at the same time.”

Loeb was 6 or 7 when she started writing songs on her piano, switching to guitar in high school.

“I really started writing at this acting summer camp in London,” she says. “I borrowed a guitar from one of our teaching assistants, and there was a string missing, but I’d write songs on this guitar. I was in a dorm room and people would come into the room and want to hear my own songs, so I would play them. And just having that immediacy of playing a song and then connecting with an audience and having so much feedback from the people who would listen and wanted cassette tape copies of my songs, it gave me early on a habit of getting feedback pretty immediately.”

She still appreciates that sort of instant feedback.

“I’ve been playing some new songs I’ve written for a record I have coming out,” she says. “And it’s that old-school feeling of people hearing music for the first time and coming up after the show and saying, ‘Oh, when can I get a tape of that?’ Or not a tape. But you know, ‘When can we get that music?’ So having that fresh sense of connecting with an audience on new music, it’s still really exciting.”

Twenty-five years after scaling the charts with “Stay (I Missed You),” Loeb is on her way to Zia Records to celebrate the release of a limited-edition 12-inch color vinyl record of her breakthrough hit with four additional never-before-released live versions of fan favorites.

And even after all this time, she says, performing “Stay” is “really something I enjoy. I play concerts a lot still and put out records, but people still feel such a strong connection to this song, both in a nostalgic and a very present way. So it’s really fun to be able to celebrate that with my fans and people who love listening to music.”

Reach the reporter at [email protected] or 602-444-4495. Follow him on Twitter: @EdMasley.

Lisa Loeb

When: 1 p.m. Friday, Nov. 29.

Where: Zia Records, 3201 S. Mill Ave., Tempe. 

Admission: Free.

Details: 480-829-1967, ziarecords.com.

Read or Share this story: https://www.azcentral.com/story/entertainment/music/2019/11/25/lisa-loeb-interview-happy-celebrate-25-years-stay-i-missed-you-tempe-zia-records/4265138002/