Pride headliner Lisa Loeb makes her own ‘Rainbow Connection’

It’s been 25 years, almost to the week, since Lisa Loeb’s yearning “Stay (I Missed You)” became the Number One record in the United States, turning the shy, bespectacled Texan into an unlikely pop star.

Although she never scaled those lofty heights again, Loeb had a few more chart hits, and a more-than-respectable couple of years as a major-label artist.

She’s the headline performer at Friday’s St. Pete Pride celebration concert at North Straub Park.

As the music business changed, so too did Lisa Loeb. As an independent singer/songwriter, she has continued to exercise her music with a series of songs, records – and books – aimed at children and young adults.

Initially developed as a Barnes and Noble exclusive, Catch the Moon was her first such project, in 2003. “I’d always wanted to make a kids’ record, because I loved music and entertainment from when I was a kid,” Loeb, 51, explains in a phone interview. “It wasn’t always geared towards kids, everything from The Carol Burnett Show and Fernwood 2Night to actual kids music like Free 2 Be You and Me, the Marlo Thomas record. I loved all that stuff, and I wanted to make something like that. I’d made so many grownup records.”

Her sweet, childlike singing voice and plainspoken delivery, it turned out, were ideal for telegraphing messages of positivity, hopefulness and the sheer joy of living to youngsters.

Catch the Moon, Loeb explains, “was more about being nostalgic for my own childhood. But as I got pulled into it more, my second record was a summer camp songs record. Music meant a lot to me at camp. We sang all the time.

“So I paired up with some collaborators who also had gone to summer camp, and loved summer camp. And together we wrote summer camp-inspired songs. Which sounded like songs we might have listened to in summer camp.”

(2008’s Camp Lisa included such originals as “The Disappointing Pancake,” “Best Friend” and “The Wake Up Song,” along with singalong stalwarts like “Peanut Butter and Jelly” and “Home on the Range”).

She and Roey Carmichael, her husband of 10 years, have two small children. The arrivals of Lyla and Emet were milestones in Loeb’s career, too.

“Finally, I had kids and I realized kids also like classic kids’ songs, especially when they’re little. So I did three albums for Amazon – the first one was Nursery Rhymes, and the second one I returned to writing original songs again, which is the one that won the Grammy.”

That was 2016’s Feel What You Feel, followed by her soundtrack for If You Give a Mouse a Cookie, which was in turn followed by Lullaby Girl – a collection of pop classics (“What the World Needs Now,” “In My Room,” “The Rainbow Connection,” Fleetwood Mac’s “Don’t Stop”) sparsely arranged and impeccably produced.

Loeb is – understandably – proud of the direction children’s music has taken her. “Instead of it being watered down, the production and the songwriting are the same exact level as any other record,” she explains. “I feel like we’ve been able to explore more themes, more genres, more instrumentation, things that really connect with people at all ages. And it feels really creative and fun to do, from the artist standpoint.

“And it also has been affecting my quote-unquote grownup music. I’m working on finishing up a grownup record right now. When you collaborate with other people you really have to focus on ‘What are you trying to say?’ It’s not just you and your mind and your pen, it’s a group of people making something. So you all have to know what you’re all making.

“And I think’s kind of rubbed off on me in my grownup music. So I think more about what do I want to say, and how can I say this in a way that’s not hitting somebody over the head with my values, or anything. But telling a story so that hopefully they can share my experience and my point of view.”

She was just another New York coffeehouse artist when her demo of “Stay (I Missed You)” found its way onto the soundtrack of the hugely successful Gen-X comedy Reality Bites in 1994 (the long backstory includes the fact that the film’s star Ethan Hawke was Loeb’s friend and neighbor in Greenwich Village).

She became the first artist to top the Billboard Hot 100 without the benefit of an actual record-label contract.

“It really kick-started my big professional career,” Loeb says. “It gave me confidence that like wow, I’ve been doing this for many, many years – and I’m so excited that I get to do it professionally for real, for real. To have that much positive feedback, it blasted me into space. As far as being out there in a commercial way.

“It gave me a connection to people in the entire world, through just that one song. It’s given me the ability to make music – and to have a lot of creative control over what I’m doing.”

These days, she adds, “It’s not all about having a hit single. You find that out after you do have some hit singles. I think it’s important in life and in business to look at things in different categories. And one of them is: The things that you can totally control.

“For a musician, the things you can control are like writing a song that you’re really proud of, playing a bunch of gigs and playing in front of a lot of people who pay you money to come see you play, and you get to hang out with them and play music for them.”

And that’s where St. Pete Pride – where all Lisa Loeb’s music is “grownup music” – comes in. “It’s a big message in my songs, that it’s really important for people to be able to be themselves. To have their opinions, to be who they are, be true to their own heart. And this is an event that celebrates that.

“It’s important to be able to respect each other, and communicate with each other; it also celebrates that. And that’s just at the core of who I am, and what I believe, and it comes through my songs. I’m so excited to be part of that celebration.”

Admission is free, although VIP packages are available. All info here.