2003–2005: Gameface and self-titled album In 2003, Sillona signed a contract with
Universal Records and released his debut album
Gameface, which included two Tagalog songs — "Kaibigan" and "Bakit Pa Ba". The music video for his first single, "Design for Luv", an
R&B,
hip-hop track, was filmed in
Hollywood with Ray Brown.
Gameface was re-released in 2004 with two additional songs, later used as singles. The album was both commercially and critically successful, earning platinum certification by the
Philippine Association of the Record Industry. It was also nominated for multiple awards and won Sillona the
Favorite Male Artist award at the 2004
MTV Pilipinas Music Awards and "Best Ballad" at the
Awit Awards for "Bakit Pa Ba". In April 2004, he headlined his first solo concert, Gameface the Concert, at the Music Museum, followed by Gameface Reload in September 2004. Following the success of his debut, Sillona released self-titled
Jay R, his second album, which introduced a more
R&B-oriented sound. It included a cover of
Billy Joel's "
Just the Way You Are" and an alternate version featuring Irish pop singer
Samantha Mumba. The album also featured collaborations with rappers Young Clipp, Jdimes, and longtime collaborators Jimmy Muna and Kris Lawrence. and achieved a gold certification from PARI. In 2004, Sillona collaborated with Filipino singer
Kyla on the single "
Not Your Ordinary Girl" from her album of the same name. The two later released additional duets, including "
Back in Time", "
Say That You Love Me", "
You Are Not Alone", and "Undeniable". That year, he made his film debut in
Happy Together and released his second studio album, a self-titled work, in 2005. In 2005, Sillona appeared in
Footloose: The Musical, alongside
Iya Villania. He contributed as a featured artist, songwriter, and producer on
Karylle's album,
You Make Me Sing.
2006–2009: Homeworkz Records In 2006, Sillona built Homeworkz, a recording studio in his home, and established his label, initially named JAYRS Music. He described the studio as a cost-efficient and convenient space for recording, which he designed to resemble a modern bachelor pad. Early in 2008, Sillona released
Soul in Love, a
cover album, featuring R&B and
jazz classics that influenced him. The album was well-received, achieving gold certification in the Philippines and later earning platinum status. The album won him the R&B Artist of the Year award at the 2008 Philippine Hip-Hop Awards and a nomination for Best Male Soul/R&B Artist at the inaugural
Wave 89.1 Urban Music Awards in 2009. To support the album, Sillona performed in Japan and collaborated with artists including Iya Villania,
Kris Aquino,
Kris Lawrence, and
Billy Crawford.
2010–2012: Jay R Sings OPM Love Classics and international exposure In early 2010, Sillona released
Jay R Sings OPM Love Classics, an all-Tagalog cover album. The album features 13 songs recorded by prominent
OPM artists in the 1980s and 1990s.
Inquirer Entertainment commended the album for Sillona's vocal ability, stating that his voice "practically breezes through most of the ballads". He appeared as a performer on GMA Network's musical variety show
Party Pilipinas and served as the host of the Philippine adaptation of the dating game show
Take Me Out. On September 2, 2010, Sillona signed a three-year contract with Tarra Group Indonesia in
Jakarta. As part of this contract, Sillona collaborated with Indonesian pop artist Drimi on "Kau Dan Aku".
2014: Elevated album Sillona released his album
Elevated in 2014, under his label Homeworkz. The single "Tonight", featuring Mica Javier, rose to the top of the radio charts at No. 1 and was awarded Best R&B Song of the Year by Wave 89.1 FM and 93.1 Monster FM. The album was awarded gold status by PARI during the ABS-CBN TV show
ASAP on Channel 2. In 2014, after over a decade with
GMA Network, Sillona transferred to
ABS-CBN. He debuted on the network as a contestant on the impersonation competition
Your Face Sounds Familiar, marking his first appearance on a reality show. In 2016, Sillona was announced as a member of the R&B group ASAP Soul Sessions, along with
Jason Dy,
Daryl Ong,
KZ Tandingan and
Kyla. The group formed on May 15, 2016, and disbanded in late 2017.
2017–present: Kamusta Ka album In late 2017, Homeworkz launched a teaser single entitled "Kabilang Dako" written by Thyro and Jay R. The song won R&B Song of the Year at the Wave 89.1 FM and Wish FM Awards. In 2018, Sillona signed with Cornerstone Entertainment. == Acting career ==