Cannavale began his acting career in the theater – with no acting training – and gained early film roles in Night Falls on Manhattan (1997) and The Bone Collector (1999), Cannavale became well-known when he starred as Bobby Caffey for two seasons on Third Watch. Following this, in 2001, he starred with Alan Arkin in 100 Centre Street – which was written and directed by Sidney Lumet, his then-father-in-law.
In 2002, he joined the cast of Ally McBeal for the last five episodes but the show was then cancelled. Following this, he starred with Yancey Arias and Sheryl Lee in the miniseries Kingpin. In 2003, Cannavale briefly appeared on the last two episodes of Oz. From 2004 to 2006, he had a recurring guest role on Will & Grace as Vince D'Angelo, the first long-term boyfriend for Will (Eric McCormack) on the show. For this role he won his first Emmy Award as "Best Guest Star in a Comedy Series". He has also appeared in the films Snakes on a Plane, The Guru (2002), Shall We Dance? (2004) and Romance & Cigarettes (2005), and guest starred in Sex and the City, Six Feet Under, Oz, Law & Order - and its spin-off series Law & Order: Criminal Intent and Law & Order: Special Victims Unit.
Cannavale serves as the voice of Corado R. Ciarlo known as "Babe," in the Ken Burns's PBS film series The War (the story of World War II) from the perspective of the men who fought in combat and their loved ones at home.
Cannavale also read the audiobook version of Richard Price's novel Lush Life.
On August 25, 2008, ABC ordered his pilot Cupid to series. It is a remake of the 1998 program which had starred Jeremy Piven and Paula Marshall. In the new version of the series, Cannavale will star opposite Sarah Paulson. Original series creator Rob Thomas is currently overseeing script development. ABC has scheduled the series to debut in late March of 2009.
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