Lisa Loeb’s “Stay” And The Power Of Unconventional Hits

Lisa Loeb was a singer-songwriter doing the early ‘90s coffee house circuit in NYC. 

She was a comparative literature grad with a freshly formed band, Nine Stories (yes, that’s a J.D. Salinger reference), and she was trying to “make it.” Whatever make it even means. Whatever make it even meant. Yes, those are two different things, not unlike singer and songwriter, or the combined singer-songwriter, which is very different from a folk artist too, while we’re at it. 

The ‘90s were so often confusing and confused.  

Loeb self-identified as a singer-songwriter in an intentional effort to avoid being boxed into the emergent folk/feminist/women-with-guitars (or pianos) movement that was about to be everywhere. She wanted to write songs. She wanted to be known as a writer of songs. To her, that’s what a singer-songwriter does, and so that’s what she was doing: singing and writing, not folking.* 

It matters. Labels and stories and identities always do.* Because caring about the work she felt called to do is what would send her down a unique and very special path. 

In a pre-internet era, industry leads got passed around by word of mouth. A contact of hers heard Daryl Hall was looking for solo material. It came in through the grapevine, and she thought she’d have a shot with a submission. This is the writer side of trying to make it as a singer-songwriter.

Imagine her pulling all the Hall and Oates she could muster into her mind, channeling Daryl, and sitting down to write. Imagine how you would do it. Pick a favorite artist of your childhood and think how you’d approach inhabiting their powers. She’d seen Hall and Oates live multiple times, she’d grown up playing the records even more times. She could write for him and she could write through him.  

Loeb wanted to make it a breakup song. She wanted a kind of “Sara Smile” bluesy swagger with a fresh layer of forlorn despair. It prompted her to add this great, “Yeah, ah, ee-ah” in between some of the actual lyrics, which was just so Daryl Hall specific. She ended up calling the song, “Stay.” 

It wasn’t Hall’s song yet though, so she was playing it out. This is the singer side of trying to make it as a singer-songwriter. A neighbor used to come see her play. His name was Ethan Hawke. He was an actor. They were both in the arts scene and had some mutual friends from the theater district. It’s always a smaller world than you think. 

At one show Hawke asked her about working on a song for a movie he was going to be in, but the idea fizzled. Then he heard “Stay” and thought, “That’s the one.” He got a tape of it and brought it to Ben Stiller. 

A quick recording session and a short while later, moviegoers started hearing “Stay” as the second song in the closing credits to Reality Bites. It was on the soundtrack too. It started to catch people’s attention.

A song she had sung and written started to catch people’s attention.  

“Stay” started to get so much attention they updated the title to, “Stay (I Miss You)” so it wouldn’t be confused with any other songs called “Stay.” 

It started to get so much attention that Ethan Hawke got a camera and found an empty apartment they could film its now iconic one-take video in. 

The only bit that hasn’t gotten enough attention these days is the cat in the video belonged to Hawke too, which is some Popup Video information if ever there was some, and it still makes me happy to know. 

“Stay (I Miss You)” started its rise on the charts in April of 1994. By August it was in the #1 spot. Lisa Loeb had just become the first artist to have a Billboard Number One song without a record deal. 

Lisa Loeb is and was a writer and singer of songs. She did great work. It found her an audience. She’s a mother, an author, and a (by all measures) successful singer-songwriter still, 30+ years later. 

***

I love this story so much. 

And, 

I’m clearly stuck on a theme this week. 

Don’t chase fame. 

Chase doing good work. 

You never know what might happen. 

Just ask Lisa Loeb, Ethan Hawke, Ben Stiller, and especially, my friend Jeff, who used to crack us up in 7th grade with his dramatic lip-synched + danced reenactment of the entire video.  

Good things come to those who do uncompromisingly good work. 

The world is smaller than you think. 

You don’t need all the fans, but you want the right ones - so do the work that attracts them. 

***

Here’s Lisa Loeb performing the song with Daryl Hall and telling part of the story. It’s a magic clip. Especially them working out some details on the spot, because it’s an insanely complicated song (Stereogum has a great writeup on this, I could write an essay on how wonderfully weird this song is as a composition). 

Here’s the OG video, featuring Ethan Hawke’s cat, Loeb’s famous glasses, and I kid you not - my friend Jeff had the physical routine memorized and it killed. 

For added/good measure - this duet version of “Rich Girl” they did on the show is so fun too. Jump to 2:50 if you want to skip the food bit. The collaboration is so fun to see as they work it out. Song starts around 4:30. 

Ps. (719)266-2837 still works. 

*The Paul Westerberg album, Folker, is one my favorite of his solo projects. I also think it has one of the funniest names ever and I’ve often wished I had the term in ‘94 instead of ‘04. At least I can still pull off a reference in ‘24 I guess.  

Pss. I loved this stories and scripts discussion so much, and I feel like it applies on so many levels to this story. Plus, you have to make your own path, you have to leave yourself open to the optionality of surprises. These synchronicities do not escape me.