Toby Lightman was late for our interview, though when she did arrive she was full of apologies (she does have two kids under the age of 5) and even bore a gift.
"You probably don't have a CD player," she laughed, handing over a CD of her latest album, "After All."
She was right. Not that it matters, because her music is all over Spotify, Apple, YouTube. But that 5-inch-by-5-inch box, featuring a watercolor-style rendering of Ms. Lightman, a singer-songwriter with considerable accomplishments under her signature wool fedora, was emblematic of something else: She belongs to a time when pop music was simply sweeter.
We're talking about the early aughts -- post-angry Alanis Morissette and pre-Miley Cyrus writhing around on a wrecking ball. Beyonce had just gone solo and Hilary Duff took her honest-to-goodness Disney persona and sold it to the tween set. Kelly Clarkson had just won "American Idol."
Into this seemingly less cynical decade came Ms. Lightman. It was 2004 and she had been signed by Jason Flom for his Lava Records label, a subsidiary of Atlantic Records. She released her first album, "Little Things," which invited comparisons to Nelly Furtado, Mary J. Blige, and Sheryl Crow, with reviewers touting her "strong vocals" and "huge voice." Meanwhile, her single "Devils and Angels" reached number 17 on the Billboard adult top 40 chart.
Conan O'Brien also took note and invited her to perform on his late-night show, which she did -- twice -- and that led to something far more wondrous.
"Prince called to ask if I would open for him," she said, beaming, as she recalled what was, understandably, one of the great highlights of her career. "I was on tour with Gavin DeGraw at the time, and my whole band and I left to fly to Prince's 'Musicology' tour in Portland, Oregon."
The music legend rarely employed opening acts. "I was one of maybe five artists he offered a show," she said. Prince had heard her sing and play guitar on Conan O'Brien's show and loved her strong chords and powerful voice.
During the pre-concert soundcheck, she remembered being on Prince's purple stage when all of a sudden the arena went quiet. She turned around and found herself face-to-face with the seven-time Grammy winner, who actually said, " 'Thank you for leaving your tour and being here.' I almost fainted."
Following the performance, Ms. Lightman and her band were invited to the after-party, held in a bar that had been closed for the occasion. Prince arrived, she said, sat down at a table next to her, and they talked for three hours, instilling in her a notion that she didn't have to be a major-label puppet. "He told me, 'You can do this on your own. You don't need a major label. You can produce on your own.' "
"Stuff like that doesn't happen to a little Jewish girl from New Jersey!" she exclaimed last week in Springs, where she and her husband have a second home.
Indeed, Ms. Lightman, from Cherry Hill, N.J., stands at about five-foot-nothing, making her powerful, throaty vocals all the more startling. It was during her high school graduation ceremony that she realized her voice might offer something special. She had grown up studying the violin via the Suzuki method, which emphasizes the importance of listening and repetition, so she always knew that she could hear the right notes and sing on pitch. But when she sang a rendition of "Bridge Over Troubled Water" at her graduation, her first time performing for a large audience, she said, "I moved people to tears. It was mind-blowing, but I had no idea what it all meant."
She went on to study at the University of Wisconsin, where she played club lacrosse, taught herself guitar, met other musical kids, and enjoyed the freedom to write and sing. During the summer after her junior year, she interned as a runner at Smokin' Grooves, a legendary hip-hop festival that was making a stop in Philadelphia, where met the rappers Wyclef Jean and Public Enemy, as well as Wyclef's brother Sam Jean, who she hoped might connect her further to his famous brother.
Simultaneously, she also met an aspiring boy band. They had been signed by an Asian label and were looking for a backup singer. So, she dropped out of college and spent six months in Thailand singing cover songs for the boy band. "But Wyclef's brother kept calling me," she said. "And this was before cellphones, so he'd call on a landline, promising that if I returned to New York, he'd help me."
She returned, but first went back to college, doubled up on classes, got her degree, and then moved back to New Jersey around 2000. Sam Jean delivered on his promise, regularly sending her to Wyclef's studio sessions, where she learned to program beats. She produced two songs that she sent around to labels and eventually landed a manager. Within a year, at age 24, she had her record deal with Lava Records.
"My musical input was pretty different. I play strong chords so I was playing the guitar and singing a soulful style of pop music. I played more aggressively than, say, Jewel at the time."
Under the Lava label, she did the late-night circuit, the radio circuit, and toured with Jewel, Rob Thomas, Gavin DeGraw, O.A.R., Marc Cohn, and others. By 2006, however, Atlantic Records parted ways with Lava Records but retained Ms. Lightman, releasing her second album, "Bird on a Wire."
One of the songs, "My Sweet Song," was featured in "P.S. I Love You," a 2007 Hilary Swank movie. It's a dusky, folksy ballad that played during a two-minute-plus climactic scene in which Ms. Swank bawls the entire time. "My music does tend to live in scenes when people are crying. Something really disastrous just happened, and they have to feel something," Ms. Lightman said, smiling.
Her commercial success notwithstanding, she felt lost in the bigger, more corporate world of the Atlantic parent company and struggled to find a place for her music. In 2009, she went independent, releasing her third album, "Let Go," under her own label, T Killa Records. Social media was as yet not a feasible self-promotion tool, so Ms. Lightman got creative: She became the first independent artist to perform on the Home Shopping Network.
"I just went down to Tampa, performed, and then watched the ticker as sales started to come in. It made me realize there are so many different ways -- and you gotta try different ways -- to expose your music. What it taught me was that I could own more of my profits being independent."
Having solidified her working relationships with some of the best producers and mix engineers in the industry, she was able to release studio-quality work, resulting in a number of TV and film placements of her songs, which offered Ms. Lightman a lucrative source of income.
"On the other hand, radio dried up the minute I left the label," she admitted, speaking about the barriers that indie artists face.
WEHM, the Manorville-based radio station heard here, played her regularly while she was at Atlantic, she said, but hasn't since she left. In 2022, following the release of "After All," her first entirely solo-produced album, she contacted the station. "I told them that I recorded part of this album in Springs, so, didn't they want to play it?" They didn't.
Now married for over 10 years and with young children, Ms. Lightman seems to exude a renewed sense of what's important, and what really is not. Having children has changed her music, further blurring her genre boundaries. After watching "Sesame Street" relentlessly with her older son, she's now writing music for the show.
She's also in collaboration with a Philadelphia rapper named Frzy, developing a storyline about the unlikely friendship between a 6-foot-7 Black guy and a little, white, Jewish girl. Additionally, Ms. Lightman continues to write for Disney and PBS, commercials and films, and she'll return to limited touring in the fall.
But her albums are where her emotions clearly live, with songs steeped in messages of motherhood, infertility, and support for the L.G.B.T.Q.+ community. "I'm making music I love and with the confidence now to produce it to be as high quality as when I was signed. It's refreshing and daunting," she said.
Still, wouldn't she love to be back in the heady days of performing in packed arenas and expense-account touring?
"Would it be great to win the lottery again? Sure. But I already won it. I did get to perform on 'Letterman.' I met Prince. It was like a dream. So, I feel really lucky all that happened. And maybe it'll happen again."
