Dillon began his career on YouTube, uploading his first public video to his channel, PICKLEandBANANA, in 2010. Over his five years on YouTube, Dillon has amassed over 2.6 million subscribers on his channel, as well as more than 175 million views on his videos. Dillon also gained exposure due to the YouTube supergroup 'Our2ndLife' where he, Connor Franta, Justin Caylen, Kian Lawley, Trevor Moran and Sam Pottorff went on an international tour and amassed a total 2.7 million subscribers before the group broke up in December 2014. He is also partnered with Fullscreen and has participated in their In Tour festival.
Dillon uploads original songs and covers, as well as music videos on his channel. He also starred in a scripted Sour Patch Kids series, titled Breaking Out. Dillon was also a member of a YouTube collaboration channel, known as Our2ndLife until it disbanded in February 2015.
In 2014, Dillon released his debut single, titled "Ordinary". Dillon's debut EP, titled RPD, was released on January 26, 2015. In July 2015, Dillon released his sophomore single titled "BEAT". In an interview with People Magazine at VidCon 2015, Dillon hinted towards a new personal song called "Gold", told to be featured as one of the tracks on his second EP.
Dillon has mentioned in multiple interviews that Demi Lovato is a major influence to his musical career. He has covered several of her songs on his YouTube channel some of which were released to iTunes.
On December 1, 2015, Dillon announced the release of his debut album Gold, which is due to be released on January 15. The 10-track set is preceded by the lead single "Steal the Show" (featuring Trevor Moran) released on December 28. Snoop Dogg and fellow YouTube personalities Trevor Moran and Shelby Wadell feature on the album. The music video for the second single "Problematic" (featuring Snoop Dogg) was released on January 15.