90s Pop Singer Unrecognizable After Years—Guess Who?

She was the first artist ever to have a number-one single on the Billboard Hot 100 chart without a recording contract.

And on Tuesday, this 90s songstress, now 57, was spotted looking unrecognizable as she stepped out in Los Angeles.

The pop icon looked casually cool, wearing a grey t-shirt with the slogan ‘wild and free’ along with a pair of white shorts.

Her brunette tresses cascaded down in light waves, and she carried a silver coffee tumbler and a pink cellphone in her hand.

This Grammy Award-winning American singer shot to fame in part through her friendship with actor Ethan Hawke.

Can you guess who she is?

This 90s Grammy-winning pop star, now 57, was looked unrecognizable as she stepped out in Los Angeles on Tuesday. Can you guess who she is?

That’s right, it’s ‘Stay (I Missed You)’ hitmaker Lisa Loeb!

The song helped her become the first artist to land a number-one hit on the Billboard Hot 100 chart without a record label.

Loeb’s big break happened through her friendship with Hawke, who was her neighbor in New York City.

The two met in the NYC theater community, with Loeb telling Cosmopolitan that she ‘made music for his plays.’

The singer gave Hawke a version of ‘Stay (I Missed You)’ and he proceeded to give it to director Ben Stiller, when they were making the 1994 film Reality Bites.

Stiller ended up using the song in the film’s ending credits.

Hawke also directed a one-take music video for the hit, shot by Robin Buerki.

Loeb and her band Nine Stories were nominated for the Grammy Award for Best Pop Performance by a Duo or Group with Vocals for the song, and were named Best International Newcomer in the Brit Awards.

That’s right, it’s ‘Stay (I Missed You)’ hitmaker Lisa Loeb!; She is seen in the 1994 music video

The pop icon looked casually cool during her outing, wearing a grey t-shirt with the slogan ‘wild and free’ along with a pair of white shorts

Loeb’s big break happened through her friendship with actor Ethan Hawke, who was her neighbor in New York City and passed her song ‘Stay’ to director Ben Stiller; The two seen on set of the music video

Hawke also directed a one-take music video for the smash hit; The two pictured on set

Stiller ended up using the song in the 1994 film Reality Bites; Hawke and Winona Ryder seen in a still from the film

The song helped her become the first artist to land a number-one hit on the Billboard Hot 100 chart without a record label; Seen with Hawke in 2017

Following the success of ‘Stay’, Lisa scored two more top-20 singles with ‘Do You Sleep?’ (1996) and ‘I Do’ (1998); Seen in 2024

Last year, Lisa shared her thoughts on why the song has remained so popular with fans over the years.

‘It’s such a nostalgic song. It reminds them of their life 30 years ago or when they first heard it on a TV show,’ she told People.

‘It’s been in different commercials and TV shows, and it’s wonderful to see people’s nostalgic connection with it as well as their current connection with it as kind of a heartbreak-relationship-overthinking song.’

‘When I wrote it, it was an expression of an argument I was going through at the time. I enjoyed performing it, and it was a song that very quickly, people in my audiences in the early ’90s and in New York City, they connected to it, which is why Ethan Hawke wanted to pass the song along to the director of the movie Reality Bites,’ she explained.

Following the success of ‘Stay’, Lisa scored two more top-20 singles with ‘Do You Sleep?’ (1996) and ‘I Do’ (1998). Both her 1995 album Tails and her 1997 album Firecracker were certified gold.

Loeb released her debut album, Tails, in September 1995.

The album was co-produced by Juan Patiño, her then boyfriend.

Loeb has released a total of 15 studio albums, including her adult contemporary and children’s albums.

In addition to her music, she is also a SiriusXM radio host and an entrepreneur with her own line of eyewear.

Each type of frame in her eyewear line is named after one of her song titles.