Kyle has collaborated with artists such as Kehlani, Lil Yachty, G-Eazy and Chance the Rapper, among others. Some of his popular songs include "iSpy", "Keep It Real", "Doubt It" and "King Wavy", released in 2015 and 2016, respectively. In 2015, Rolling Stone named him as "one of the ten artists you need to know."
Kyle started releasing mixtapes under the moniker K.i.D. starting in 2010, and in 2013 released his debut album Beautiful Loser.
In October 2015, he released his follow up album Smyle. Kyle's first music video to reach one million views was Keep it Real, which was accomplished later that year.
In December 2016, he released the single "iSpy", featuring Lil Yachty. The song gained widespread recognition for Kyle. The song peaked at number 4 on the US Billboard Hot 100 and number 14 on the Canadian Hot 100.
In February 2017, Kyle signed a deal with Atlantic Records.