Careless was founded in 2017 by
James Reid and
Bret Jackson. Reid and Jackson first met as contestants in “
Pinoy Big Brother: Teen Clash” in 2010. After their stint at the show, they formed a band called WE ARE WHATEVER. They released a self-titled EP under ABS-CBN's
Star Music. In 2013, Reid signed with
Viva Records, under which, he released two albums. Reid wanted to have creative control over his music, so in 2017, he decided to release
Palm Dreams, his debut album under his own record label, Careless. The name Careless began as an inside joke between friends after hearing a dubstep remix of “Careless Whisper.” When James was recording Palm Dreams, he was asked to give a name for the label. He came up with “Careless.” Jackson, under his stage name KINGwAw, also released his debut album,
Island City Poems, in 2017.
Palm Dream's carrier single. This was followed by a music video for
Turning Up and
The Life. All three music videos featured a guest appearance from Lustre, who also co-directed
The Life with film director
Petersen Vargas. In January 2018, Lustre released her first single under Careless, which was entitled
St4y Up. In 2018,
Curtismith, Sofia Romualdez, Astro Kidd, and Massiah joined Reid, Lustre, and Jackson in the team. Sofia joined the team after a chance meeting with Jackson in a studio. Bret was also responsible for bringing in Massiah and Astro Kidd. In the same year, Reid officially left Viva, and the label came with him, becoming fully independent. The collection features collaborations with Just Hush, Kris Delano, Billy Davis, Mandaue Nights, Jetter, Jid Durano,
Ruby Ibarra, Delinquent Society, Midnasty, and Korean rapper Avin. The release of the playlist coincided with the launch of Careless' entertainment platform,
Island City. In December, Careless held a contract signing for Lustre, Jackson, Massiah, Astro Kidd, and Curtismith. Careless also collaborated with
Mountain Dew for the launch of a new soda variant, Mountain Dew Ice, via an original song performed by Astro Kidd, Jackson, and Reid. Lustre released her debut album,
Wildest Dreams, in October. In 2021, Jolianne and hip-hop dance group A-Team joined the team. Careless collaborated with
Yamaha to promote the Yamaha Mio motorcycle. Lustre, Massiah, and Reid worked on a track called
Own It for the campaign and also appeared on the music video for the song. In 2022, Massiah released his debut album,
Lahi, in March. Lesha, Issa Pressman, and
Liza Soberano joined the team. Lesha released her debut album,
3rd Eye, in August. Reid released his second album under Careless,
loveless:, in October. August Wahh,
Destiny Rogers, and
SOS joined the team. In September 2024, Careless announced that Liza Soberano parted ways with the company, effective July 29, 2024. == Artists ==