Olan is known for Stranger Things Stranger Things (2016) Season 3.His 2020 Feature film projects are Molly directed by Sally Potter and Liberty directed by Phillipe De Witte. Other film roles include The Roads Not Taken (2020) directed by Sally Potter, Already Gone (2019) directed by Christopher Kenneally, executive produced by Keanu Reeves, Sundance feature film Appropriate Behavior (2014) directed by Desiree Akhavan, Hollywood Dirt (2017) directed by Tosca Musk, Alterscape (2018) directed by Serge Levin and Haymaker (2021) directed by Nick Sasso produced by Andrew van den Houten. Olan and his twin brother starred in the 2016 American Film Institute Film Fest official selection short Ham Heads (2016) as conjoined twins directed by Efrén Hernández as well as Frankie: Italian Roulette (2016) which won the 2015 Oaxaca Film Fest in Mexico and the Nostro D'Argento in Rome in 2016. He has written, produced and several of his own short films Rush Call Clown (2016) (winner of the Judges Award in the Discover Film Festival 2016), Silence = (2017), Babies to the world (2018), Toggle (2017) and Al & Ollie (2017). Olan is also known for his fine art portraiture both for and of several noted personalities including Alan Cumming, Rufus Wainwright, Anne Hathaway, Susan Jaffe, Ethan Stiefel, Dominic West and Courtney Love. On March 3, 2008 Village Voice columnist Michael Musto wrote an article titled "Portrait Artist makes it Big by Upping the Subculture," concerning Olan's book of portraiture, "POP, Art inspired by New York's own subcultures from celebrity to subway something more through color & light", a collection of portraiture created from a combination of Olan's own photography combined with painting and plastic. Olan Montgomery is an identical twin originally from Georgia.