He first received attention on social media by posting covers of pop songs by artists such as Austin Mahone, Taylor Swift, Rihanna, Justin Bieber, and Shawn Mendes to his YouTube channel.

[4] Citing the initial success of the first video, he and his sister continued posting covers of famous musical artists like Justin Bieber, Shawn Mendes, Taylor Swift, Austin Mahone, and Selena Gomez on his YouTube channel while Darian directed, shot, produced and edited all his videos.

In 2017, a YouTube video was posted by Glamour showing P!nk viewing his cover of her song “Just Give Me a Reason”, in which the singer noted he had “incredible voice control.” He signed with Universal Music Canada on May 18, 2018,[5] and has released singles such as "Day and Night" and "What If" (both featuring Mackenzie Ziegler),[6] "Last Summer",[7] "Waste My Time", "All These Parties", "Phobias", "See You" and "Everybody Wants You".

[8][9] Orlando embarked on his second headlining North American tour in support of the EP, beginning on April 29, 2019, in Chicago and ending on May 22, 2019, in Vancouver.

Orlando has also shared that his dad played Pearl Jam and Otis Redding in the car, which helped cultivate his songwriting skills.