Matthew Scott Montgomery's career in Los Angeles began with a significant breakthrough as Kendall Parker in Del Shores' 2010 play Yellow, which ran for an entire year. His outstanding performance earned him numerous accolades, including the Best Featured Performance in a Play at the Los Angeles Drama Critics Circle, where he was nominated alongside esteemed actors Harry Groener and Chris Pine. Additionally, he received the Best Featured Actor in a Play at the Backstage Garland Awards, Comedy/Dramatic Performance of the Year at the Stage Scene LA Awards, and was nominated for Best Performance at the LA Stage Alliance Ovation Awards.
During his run in Yellow, Montgomery was cast in the Disney Channel pilot for Shake It Up! and continued to work on various Disney Channel projects, such as Sonny With a Chance/So Random and Austin & Ally. He has since appeared on TV shows like Jane the Virgin, White Famous, Betch, and multiple episodes of Smosh. Montgomery has also been featured in two documentary series: Unidentified with Demi Lovato and Dancing with the Devil. Notably, he and Lovato have been close friends since 2011.
Montgomery has also collaborated with Shores on a live production and film version of Southern Baptist Sissies, alongside Leslie Jordan. In the Los Angeles Theater scene, he has made a name for himself, starring in Stage Kiss at the Geffen Playhouse and writing and starring in the play Dead Boys at the Celebration Theatre, partially funded by a grant from the city of West Hollywood. Montgomery has written multiple plays, with his most recent being Foursome, which is in development with his theater company IAMA Theatre.
His short film Don't Turn Off the Ghost Light has won multiple awards in the festival circuit, a reunion project with his Disney Channel co-star Allisyn Snyder (Sonny With a Chance). The two co-directed the film, with Montgomery writing and starring. His first feature, Howdy, Neighbor!, is currently in post-production, directed by Snyder with her production company and starring himself, Debby Ryan, and Alyson Stoner.