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Massoglia wrote, directed, and starred in the short film Playball, which was released online in 2018.

After a four year break from acting, Massoglia returned to the profession. His first notable work was in the 2016 film The Matchbreaker, in which he had a minor role. This was followed by the small film Because of Gràcia, in which he starred as teenaged boy trying to build a relationship with a chaste girl who refuses to kiss until she's married. In the fall of 2017, Massoglia began filming another small independent film, The Lumber Baron.

As of November 2009, most critiques of Massoglia's acting have concerned his leading role in Cirque du Freak: The Vampire's Assistant. His performance has not won raves; motion picture industry trade publication Variety said, "The production puts far too much faith in the appeal of newcomer Chris Massoglia, who plays Darren Shan, a rule-abiding, good-grade-earning conformist with the shaggy coif and bland, gumdrop charm of your average Nickelodeon character." The Boston Globe called his acting "too bland to deliver." However, reviewing his 2009 film The Hole, The Hollywood Reporter called Massoglia "a young Zac Efron... who ably carries the film."

He made his feature film acting debut in 2007 in the motion picture A Plumm Summer, but his most prominent role as of 2009 was as "Darren Shan" in the 2009 film Cirque du Freak: The Vampire's Assistant. Originally scheduled to debut in theaters in 2010, the film was moved to October 2009 to "capitalize on the Halloween season", and opened a month prior to another highly anticipated vampire picture, New Moon.

He began acting in 2003 under the name "Chris Kelly" (sometimes appearing as "Chris J. Kelly") in an episode of the television program Law & Order: Criminal Intent. The same year, he was considered for the part of 10-year-old Sean in the Nicole Kidman film Birth, but the family refused to allow him to appear naked on screen with a nude, grown woman. He auditioned for Spider-Man 2 (getting far enough in the casting process to spend an afternoon with Tobey Maguire) and Bad News Bears (he returned six times for call-backs but was not cast). He spent the summer of 2004 away from auditions to play Little League Baseball; his team (the Robbinsdale All-Stars) won the Minnesota state title that year but did not go to the Little League World Series after losing in the Indianapolis regionals. He appeared in two episodes of Medical Investigation in 2004, and four episodes of the TNT cable television police drama Wanted in 2005. He began using his family name of Massoglia in 2008.

Christopher Paul "Chris" Massoglia (born March 29, 1992) is an American television and motion picture actor.