Careless (record label)

Lore & Background

Careless was founded in 2017 by James Reid and Bret Jackson, who first met as contestants on Pinoy Big Brother: Teen Clash in 2010. They later formed the band WE ARE WHATEVER and released an EP under Star Music. Reid signed with Viva Records in 2013 but sought creative control, leading him to launch his own label. The name 'Careless' originated from an inside joke after hearing a dubstep remix of 'Careless Whisper.' Reid's debut album under the label, Palm Dreams, was released in 2017, followed by Jackson's Island City Poems. Both albums featured collaborations with Nadine Lustre, who later released her first Careless single, St4y Up, in January 2018.

Reader's Guide

Careless represents a shift in the Philippine music industry toward artist-owned labels, prioritizing creative control over corporate interests. Founded by James Reid and Bret Jackson, the label has nurtured a diverse roster of artists, from mainstream pop to underground hip-hop and dance. Its collaborative mixtapes and playlists, such as Careless Mixtape Vol. 1 and The Island City Playlist, showcase cross-genre and cross-artist synergy. The label's independence from 2019 allowed it to experiment with brand partnerships (Oppo, Mountain Dew, Yamaha) while maintaining an artist-centric ethos. Careless has also served as a platform for artists like Nadine Lustre, Massiah, and Lesha to release debut albums. Its evolution from a vanity label to a collective with a distinct identity—including the Island City multimedia platform—marks it as a notable player in OPM (Original Pilipino Music). The departure of founding member Bret Jackson (KINGwAw) and Liza Soberano in 2024 highlights the label's ongoing transitions.

Did You Know?

• The name 'Careless' came from an inside joke after hearing a dubstep remix of 'Careless Whisper.'
• James Reid and Bret Jackson first met as contestants on Pinoy Big Brother: Teen Clash in 2010.
• Careless became fully independent in 2019 after Reid left Viva Records.
• In 2020, Careless collaborated with Oppo for the Reno4 campaign, producing the track 'Clearly The Best You.'

Origins & Creative Vision

In 2010, two teenagers crossed paths as houseguests on the reality series Pinoy Big Brother: Teen Clash. That brief encounter set in motion a musical partnership that would reshape a corner of the Philippine music scene. James Reid and Bret Jackson, who performed under the stage name KINGwAw, first played together in a band called WE ARE WHATEVER, releasing a self-titled EP through ABS-CBN's Star Music. After Reid signed with Viva Records in 2013 and put out two albums, he grew restless under the traditional label structure. In 2017, he decided to take full creative ownership by launching his own imprint, Careless, and dropping his debut album Palm Dreams on it. The name itself was born from a lighthearted moment among friends who had just heard a dubstep spin on "Careless Whisper." Reid has been candid about his motivation: he saw a gap in how the industry treated artists and wanted to build a platform where creative vision came before commercial machinery. That artist-first philosophy became the backbone of everything the label would go on to do.

Building a Collective

What began as a two-person venture quickly grew into a sprawling creative family. In 2017, both Reid and Jackson released debut albums—Palm Dreams and Island City Poems respectively—and each project featured Nadine Lustre, a fellow Viva Records alumna who became an early Careless collaborator. The following year brought a wave of new signees. Sofia Romualdez stumbled into the fold after a serendipitous studio encounter with Jackson, while Bret personally recruited Massiah, who had been building a following in Dumaguete's underground scene, and Astro Kidd, a graduate in aircraft engineering and marketing management who balanced modeling gigs with underground production. Curtismith rounded out the expanded roster. Together, the group released Careless Mixtape Vol. 1, a fifteen-track collection that included a collaboration with the Cebu-based band Midnasty. By 2019, the collective had grown large enough to produce The Island City Playlist, a fourteen-track showcase featuring guest appearances from artists as varied as Korean rapper Avin, Ruby Ibarra, and Delinquent Society, alongside the launch of the label's own entertainment platform, Island City.

From Independence to Industry Partnerships

Careless navigated a deliberate path through the business side of the music world. At its inception in 2017, the label operated in tandem with Viva Records, Reid's former home. That arrangement ended in 2019 when Reid officially departed Viva and brought Careless fully into independent operation. Rather than remaining a boutique operation, the label demonstrated a knack for high-profile commercial partnerships that kept its artists visible without sacrificing their creative identity. In 2020, a group of Careless acts—including Lustre, Massiah, Curtismith, Astro Kidd, and KINGwAw—recorded and performed "Clearly The Best You" for Oppo's Reno4 smartphone launch, while Astro Kidd, Jackson, and Reid contributed an original track for Mountain Dew Ice's product debut. The next year saw a Yamaha Mio motorcycle campaign featuring Lustre, Massiah, and Reid performing "Own It." By September 2024, Careless announced a partnership with Sony Music Philippines, signaling that the label had matured into a force capable of operating at major-label scale while retaining the independent spirit that defined its founding.

Roster Evolution & Current Landscape

Careless has always been defined by its fluid, ever-expanding family of artists. The current roster includes Reid, Massiah, Jolianne, Lesha, SOS, August Wahh, the hip-hop dance crew A-Team, Issa Pressman, and Destiny Rogers. Several of these names arrived during a particularly prolific stretch: Jolianne and A-Team joined in 2021, while 2022 saw Lesha, Issa Pressman, Liza Soberano, August Wahh, Destiny Rogers, and SOS all come aboard. That same year produced a remarkable run of solo projects—Massiah's debut album Lahi in March, Lesha's 3rd Eye in August, and Reid's second Careless album loveless: in October. The label's former roster reads like a who's-who of Philippine pop and alternative music, including Nadine Lustre, who released her debut album Wildest Dreams in 2020, Curtismith, Sofia Romualdez, and KINGwAw himself. In September 2024, the label announced that Liza Soberano had parted ways, effective July 29 of that year, marking the latest chapter in a roster that has continuously reinvented itself since 2017.