Costabile was born in Washington, D.C. He is of Italian descent. He attended Gonzaga College High School, graduating in 1985, and Tufts University. He graduated from New York University's MFA program in acting in 1998.
Costabile has appeared on Broadway in Manhattan Theatre Club's revival of Translations in 2007, the musical Titanic in 1997, and The Tempest in 1995. In 2005, he appeared as Launce in The Two Gentlemen of Verona as part of the Public Theater's Shakespeare in the Park. For Caroline, or Change, the Drama Desk Award–winning musical by Tony Kushner and Jeanine Tesori (2003–2004), Costabile workshopped and performed in the original production and its Broadway transfer.
Costabile had an important role in 2009's Solitary Man as Gary, the husband of Jenna Fischer's character. He played Jennifer Aniston's attorney in the 2010 flick The Bounty Hunter. In 2012, he appeared in the film Lincoln as Republican representative James Ashley. In 2013, he appeared in Steven Soderbergh's film Side Effects as Carl Millbank and as Professor Horstein in Runner Runner. In 2016, he appeared as the Chief in 13 Hours: The Secret Soldiers of Benghazi.
He has appeared in several television commercials, including ads for Microsoft and FedEx. In 2011, he appeared in Lie to Me as Dr. Mitch Grandon, the head Doctor of a psychiatric institution in the Season 3 episode "Funhouse". In 2013, he appeared in Elementary as Danilo Gura, a custodian of a hospital in the Season 1 episode "Lesser Evils". Costabile appeared as Internal Affairs investigator Simon Boyd in the 2013 TV show Low Winter Sun. He appeared in Person of Interest in Season 1 as Samuel Gates. He appeared in The Blacklist in Season 2 as Dr. Linus Creel. He starred in the television series Dig.
