In 2015, Flynn was cast as Luke in the Off-Broadway production Kid Victory performed at Signature Theatre. This was followed in 2016 with a casting as Mike the intern in BrainDead. In 2017 Flynn returned to play Luke in Kid Victory again, this time performed at the Vineyard Theatre.
Prior to these roles, Flynn acted in various commercials and films, playing a reporter for CWW's "FL Kidcare Health," the principal on Sirens and Sid on Lost and Gone Forever. Flynn has also acted in eleven plays, including Much Ado About Nothing and The Crucible.
As of 2017, Flynn plays the character Justin Foley in Netflix's 13 Reasons Why.
