At the State University of New Paltz, New York, Scolaro wrote, produced and hosted a radio comedy program That Damn Show on WFNP FM for three years.
His early professional acting career was highlighted by three Wendy's commercials and a guest role on Sidney Lumet's "100 Centre St." In 2001, writer Steve Koren (Saturday Night Live, Seinfeld) saw Scolaro at the end of 12-hour video tape collage of actors auditioning for his NBC pilot Everything but the Girl with Tiffani Amber Thiessen.
When the pilot was beat to the line-up by Scrubs, Lester Lewis (The Office) brought him to the attention of Eileen Heisler and DeAnn Heline (The Middle) and he immediately moved to Hollywood to be a regular cast member on the second season of NBC's Three Sisters as the bartender named Gordon, love interest of A. J. Langer.
During the writers strike of 2007-08, Scolaro did stand-up performances on NBC's Late Nite with Conan O'Brien and was invited back to the channel that started his career as an intern, Comedy Central, to headline an episode of Live at Gotham.
From 2008 to 2023, Scolaro has had recurring characters on several series; the sad sack, forgetful, Doug, on TBS's Sullivan and Son, Brian the negative but competent lawyer on ABC's A Million Little Things, the ridiculous Uncle Bill on "Ten Year Old Tom", the paranormal police man Goblin on Disney's "Wizards of Waverly Place" and played numerous characters on HBO's The Life and Times of Tim and Comedy Central's "Kroll Show".