Michelle Branch and Nelly Furtado, Vanessa Carlton helped usher in a new era of female songwriters during the early 2000s. Her first single, the Grammy-nominated "A Thousand Miles," was one of the biggest songs of 2002, topping the pop charts in America and cracking the Top Ten in England. None of her subsequent singles came close to matching that song's success, but Carlton continued releasing albums into the following decade, fine-tuning a sweeping, cinematic pop sound that featured her vocals and piano skills at the forefront. Her fourth studio LP, 2011's Rabbits on the Run, became her fourth straight appearance on the Billboard 200. A series of covers she released in 2018 paid tribute to influences such as Neil Young, Lucinda Williams, and Elliott Smith.
Raised in Milford, a tiny town in eastern Pennsylvania, Vanessa Carlton took piano lessons from her mother and composed her first song as an eight-year-old. Several years later, she was accepted into the School of American Ballet in New York. Despite being one of the best dancers in her class, she became frustrated with the strictness of the discipline and began to look elsewhere for inspiration, eventually winding up at the piano located inside her Manhattan dorm. Carlton began writing songs again, reaching beyond the classical music of her youth to incorporate influences from pop artists like Tori Amos and Fiona Apple. When it came time to graduate, she halted her dancing career and enrolled at Columbia University instead, where she continued to work on her songwriting.
Carlton spent a pair of years waiting tables in Lower Manhattan, living in Hell's Kitchen, and playing open-mike events before signing with A&M Records. Label president Ron Fair took particular interest in her music and agreed to produce Be Not Nobody, which became Carlton's major-label debut in early 2002. "A Thousand Miles" was the album's crown jewel, earning three Grammy nominations and dominating radio playlists throughout the year, while "Ordinary Day" also enjoyed success as a Top 40 hit. Carlton toured heavily in support of the platinum-selling album, sharing stages with bands like Third Eye Blind and Goo Goo Dolls along the way. She also began dating Third Eye Blind's frontman, Stephen Jenkins, and duetted with Counting Crowes on a popular cover of Joni Mitchell's "Big Yellow Taxi."
Carlton began recording her second album in June 2003, with Jenkins serving as her producer, collaborator, and background vocalist. Together, the two spent a year creating Harmonium, a confessional and somewhat dark album that was markedly different from her first record. Public response was different, too, and Harmonium dropped out of the Top 40 during its second week of release. Its performance worsened Carlton's relationship with A&M, leading to her exit from the label the following year.
Carlton continued writing songs with help from Linda Perry (a collaborator from the Harmonium sessions) and Jenkins. In a surprise move, she also signed a new recording contract with The Inc., a label owned by rap mogul Irv Gotti. Perry, Jenkins, and Gotti all shared production duties on 2007's Heroes & Thieves, a diverse album that received strong reviews and peaked at number 44 on the U.S. album chart. Jenkins and Carlton ended their relationship soon after the album's release, and her tenure with The Inc. proved to be short as well. By 2010, she had partnered with another label, Razor & Tie, and briefly decamped to the U.K. to record her fourth album. Rabbits on the Run was released the following year and spent a week on the Billboard 200 at number 62. Carlton supported the album with a tour, and a holiday EP called Hear the Bells appeared that November. Over the next few years, she worked steadily on her next album while also starting a family with Deer Tick's John McCauley; the pair married on December 27, 2013 and had their first child in 2015. Later that year, Carlton released her fifth album, Liberman, which was greeted by positive reviews. The album's accompanying tour was captured on Liberman Live, which appeared in October 2016. A live EP titled Earlier Things Live followed in 2017.
Carlton released monthly covers that were later collected on Double Live & Covers, a triple-vinyl set that also included Liberman Live and Earlier Things Live. It was issued by Dine Alone in late 2018.