Chris Caldovino was born in Brooklyn, New York. He began studying acting in New York at the Gene Frankel Theatre. Chris then moved to Los Angeles and quickly began gaining experience in film and television, continuing his training at Playhouse West under Jeff Goldblum. Later, Chris studied with Robert D'Avanzo at the Tamarind Theatre, where he participated in numerous stage productions. In 2004, Chris landed the recurring role of Billy Leotardo on the HBO series The Sopranos (1999). He subsequently landed many other roles on television and in film, including the FOX series Good Guys (2010) and the film Brooklyn Rules (2007) with Alec Baldwin.

Chris appeared in Martin Scorsese's Oscar-nominated film The Wolf of Wall Street (2013), written by Terence Winter, and in the film Stealing Cars (2015), produced by Oscar nominee Rachel Winter of Dallas Buyers Club. In 2015, Chris completed a three-season run as Tonino Sandrelli on the HBO series Boardwalk Empire (2010), for which he and the cast received a Screen Actors Guild Award nomination for Outstanding Performance by an Ensemble in a Drama Series. More recently, Chris has appeared in guest roles on television series including Castle (2009), The Haves and the Have Nots (2013), and Tommy (2020) with Edie Falco. The crime comedy Made in Chinatown (2021), in which Chris appears alongside other Sopranos actors, was recently released. He will also appear in the upcoming crime thriller The Getaway, filming in upstate New York in the fall of 2021, and will appear in a guest role in the tenth season of American Horror Story (2011). Chris is represented by McGowan/Rodriguez Management and Momentum Talent and Literary Agency.