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His performance on Boardwalk Empire won critical acclaim, earning him the Primetime Emmy Award for Outstanding Supporting Actor in a Drama Series in 2013.
That same year he also played Lewis, a vengeful clown on Modern Family during the third season, for which he was nominated for Best Guest Performer in a Comedy Series at the 2nd Critics' Choice Television Awards in 2012.
He appeared in The Take (2007) alongside John Leguizamo and Tyrese Gibson, as Agent Steve Perelli. Ciarlo, known as "Babe", in the Ken Burns 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.
He later starred in the Broadway play The Motherfucker With the Hat alongside Chris Rock and Annabella Sciorra.
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.
Cannavale was hired by Ken Corday and portrayed the evil, charming, sometimes humorous and manipulative mobster, Rocky Lane on Days of our Lives in June 2002.
From 2004 to 2006, he had a recurring guest role on Will & Grace as Vince D'Angelo, the boyfriend (and eventual husband) of Will Truman (Eric Mc Cormack).
For this role, he won the Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series in 2005.
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Cannavale also had a recurring role on the NBC comedy series Will & Grace as Will Truman's long-term boyfriend Officer Vincent "Vince" D'Angelo, for which he won the 2005 Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series, and portrayed Gyp Rosetti during the third season of the HBO drama series Boardwalk Empire, for which he won the 2013 Primetime Emmy Award for Outstanding Supporting Actor in a Drama Series.