Alessia Caracciolo hails from Brampton, Ontario, where she attended Cardinal Ambrozic Catholic Secondary School. Her family is from Calabria. Her father was born in Canada to Italian parents and her mother is an Italian immigrant. She can speak Italian. As a child, she wrote poetry and did theatre. She began playing guitar at the age of 10 and taught herself how to play various songs. At the age of 13, she began her own YouTube channel where she posted covers of songs that she performed.
From January to April 2016, Cara embarked on her first headlining tour, the "Know-It-All Tour," performing in various US and Canadian cities. She was short-listed for the BBC Music Sound of... award for 2016 and finished as the runner-up. Cara was awarded as Breakthrough Artist of the Year at the 2016 Juno Awards. On March 7, 2016, Cara released a music video for "Wild Things." In April 2016, Cara was announced to be one of the supporting acts of British alternative rock band Coldplay in the European and North American legs of their A Head Full of Dreams Tour, alongside British singer songwriter and Grammy winner Foxes. On June 23, 2016, Cara was featured in a re-released version of the song "Wild" by Troye Sivan. The music video was released on July 22, 2016. She played Glastonbury Festival on June 24, 2016, in the John Peel tent. The music video for Cara's single "How Far I'll Go", from the Disney film Moana, was released on November 3, 2016, and since then has received over 200 million views on YouTube. The song was written by Lin-Manuel Miranda, produced by Oak Felder, and the video was directed by Aya Tanimura. On December 15, 2016, Cara released a music video for "Seventeen."
Cara performed as the musical guest on Saturday Night Live on February 4, 2017. On April 18, 2017, the music video of the song "Stay" by Zedd featuring Cara was released. Cara featured on the song "1-800-273-8255" from Logic's Everybody album. The song was released as a single on April 28, 2017 and also features American singer-songwriter Khalid. Cara also made an appearance in the video, which was released on August 17, 2017.
2018-present: The Pains of Growing and This Summer
Cara performing in Sydney, Australia in 2018
On January 28, 2018, Cara was named the Best New Artist at the 2018 Grammy Awards, making her the first Canadian artist to win this award. On June 1, 2018, Cara released a teaser video following a week of cryptic Twitter posts. On June 9, she posted lyrics to a new song on her social media accounts for fans to piece together. Once completed, she announced the single's cover and name on June 11. The single, entitled "Growing Pains", was released on June 15, 2018. Its music video was released on June 20, 2018, and was nominated for Best Cinematography at the 2018 MTV VMAS.
On July 10, 2018, Cara announced that she would be releasing a song she made in her basement, written and produced by her, the next day, as a small gift for her birthday. The single, titled "A Little More", was released on July 11, 2018, with the music video also released the same day. On September 29, 2018, the Canadian Football League announced that Cara would be the halftime performer at the 106th Grey Cup. In October 2018, she collaborated with Italian singer Eros Ramazzotti for the song "Vale per sempre", from the album Vita ce n'è. On October 5, 2018, Cara released another song, entitled "Trust My Lonely". A music video for the song was released the same day. On November 8, 2018, a music video for the song "Babies" by Kyle featuring Cara was released. On November 13, 2018, Cara released another song, entitled "Not Today." The release date coincides with the three-year anniversary of the release of her debut album. Cara's second studio album, The Pains of Growing, was released on November 30, 2018. It reached number 1 on the US iTunes Pop Chart less than two hours after its release. Despite its position on iTunes the album debuted at number 71 on the Billboard 200 albums Chart; 62 positions lower than her debut in 2015. "Out of Love" was eventually serviced to contemporary hit radio as the album's third single in January 2019. Cara also collaborated with Alec Benjamin on "Let Me Down Slowly", which was released on January 7, 2019. On February 21, Cara announced she would join Shawn Mendes as the opening act on his self-titled world tour for the European, United Kingdom, and United States legs. In May, she headlined the "The Pains of Growing Tour," visiting Canadian cities in the month of May.
In July 2019, Cara announced the release of an EP, This Summer, with tracks to be issued "every couple of weeks" leading up to its release on September 6, 2019. She also announced that she be adding a new leg of "The Pains of Growing Tour," visiting various US cities in October and November. The first single of the EP, "Ready", was released on July 22. The second single, "Rooting For You," was released on August 9. The third single, "OKAY OKAY," was released on August 23. The fourth single, "October," was released on September 3. The music video for "October" was released on October 1, 2019.