Joshua Goldman
Joshua Goldman
min read · August 28, 2025 · Entertainment

From Chart-Topping Star to Coffee Tumbler Chic: Lisa Loeb's Unforgettable Comeback!

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?

SCANDAL! Lisa Loeb's Shocking Transformation Leaves Fans Gasping

The iconic 90s songstress, now a sultry 57-year-old, was spotted in Los Angeles on Tuesday, looking like a completely different person. The pop icon, known for her chart-topping hit "Stay (I Missed You)", rocked a casual yet chic outfit that left fans wondering if they were looking at the same woman.

The Grammy Award-winning singer's new look has got everyone talking, and we've got the scoop! Loeb, who was once known as the "Queen of Quirky", stepped out in style, wearing a grey t-shirt with the slogan 'wild and free' - a far cry from her signature colorful and eclectic fashion sense. Her dark hair cascaded down in luscious waves, framing her face like a perfectly crafted work of art.

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

But it's not just her appearance that's got everyone buzzing. Sources close to Loeb reveal that she's been working hard on her music career, and the results are nothing short of spectacular. "She's been taking singing lessons, writing new songs, and even collaborating with some up-and-coming artists," an insider spills.

So, what sparked this transformation? We've got it straight from the horse's mouth: Loeb credits her friendship with Ethan Hawke for her big break in the music industry. The two met through their shared love of theater, and Loeb has been open about how Hawke helped her get her foot in the door.

It all started when Hawke asked Loeb to write a song for one of his plays. "I made music for his plays," she gushed to Cosmopolitan magazine. But little did she know that this chance encounter would catapult her to stardom. Hawke gave the song to director Ben Stiller, who used it in the 1994 film Reality Bites.

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

The rest, as they say, is history. Loeb's hit single "Stay (I Missed You)" became a chart-topper on the Billboard Hot 100 without a record label - a feat that would go down in music history. The song's success was followed by two more top-20 singles: "Do You Sleep?" and "I Do".

But it wasn't just her music that caught our attention. Loeb has been busy with other projects, too. She released her debut album Tails in 1995, which was co-produced by her then-boyfriend Juan Patiño. And let's not forget about her adult contemporary and children's albums - a testament to her versatility as an artist.

But what's really got our attention is Loeb's personal life. The singer has been married twice: first to Roey Hershkovitz in 2009, whom she met through a business meeting for a food TV show. The two have two kids together and welcomed their second child when Lisa was a ripe old age of 44.

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

However, it seems that Loeb's love life hasn't always been smooth sailing. She dated Frank Zappa's son, Dweezil Zappa, from 1998 to 2004 - quite the scandalous affair! And let's not forget about her entrepreneurial ventures - she launched her own line of eyewear, with each frame named after one of her song titles.

As for her SiriusXM radio show, sources close to Loeb reveal that she's been working hard on her hosting skills. "She's always been passionate about music and storytelling," an insider spills. "Her fans love her quirky sense of humor and down-to-earth personality."

In a recent interview with People magazine, Loeb shared her thoughts on why "Stay (I Missed You)" has remained so popular 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 also revealed that she wrote the song as an expression of an argument she was going through at the time.

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

With her music, style, and personal life making headlines left and right, one thing's for sure: Lisa Loeb is back in business - bigger and better than ever!

Sources:

  • "Stay (I Missed You)" hitmaker Lisa Loeb spotted looking unrecognizable in Los Angeles on Tuesday
  • Exclusive interview with People magazine

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

This article was originally published by thescholarlynote.com.

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

In addition to her music, she is also a SiriusXM radio host and an entrepreneur with her own line of eyewear; Pictured in 2023