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In 2005, in GMA Network fantasy series Encantadia, Trillo was cast as lead character in Etheria, where he portrayed the Sapirian prince, Raquim.Midway through the series, GMA Network management announced that Trillo would be pulled out from the said show to once again star in another fantasy-themed television series Majika, in the end Trillo was allowed to complete Etheria.He also starred in an afternoon family drama Now and Forever: Agos where he received a Best Drama Actor nomination from PMPC Star Awards for TV.That same year, he reprised his role for Mulawin: The Movie, and appeared in the film Blue Moon.
At ang guy na ito rin ang kasama nga ni Heart sa Boracay nitong nakalipas na Undas, na ekslusibo ngang nakuhanan ng ating kamerang-gala (Parazzi photog), tulad ng makikita sa mga larawang ito. ” At dahil nasa early stage pa lang sila, napakaaga pa rin daw para pag-usapan ang kasal.
He played Gabriel, a half-Human and half-Ravena who became the third wheel in Alwina (Angel Locsin) and Agiluz' (Richard Gutierrez) romance.
The same year, he had his breakthrough performance when he starred in the Metro Manila Film Festival official entry Aishite Imasu 1941: Mahal Kita as a transgender woman during World War II.
He also starred in the horror-suspense film Pamahiin and was included in the network's noontime show SOP as a co-host where he also played drums as part of the show's "Starband".
Trillo released his self-titled debut album in 2007 under Indi Music.