Cyler was raised in Jacksonville, Florida, the youngest of three children of Katina, a cook, and Ronald Cyler, a truck driver. His parents, who were working but struggling, sold what they had to move from Florida to California in 2013. They were homeless until shortly before he landed his role in Me and Earl and the Dying Girl. Cyler also finished High School in California.
In 2013, Cyler appeared in the short film Second Chances. In 2015, Cyler got his biggest acting break when he co-starred in the film Me and Earl and the Dying Girl, based on the book of the same name by Jesse Andrews. The film had its world premiere at the Sundance Film Festival on January 25, 2015. Shortly after the premiere, Fox Searchlight Pictures acquired distribution rights for the film and released it on June 12, 2015. In 2016, Cyler appeared in the HBO series Vice Principals.
On September 13, 2017, it was announced that Cyler will join as a series regular in the third season of the MTV slasher television series Scream. He will star in the role of Deion Elliot.
