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. He also appeared in the film
The Station Agent as a man who befriends a little person removed from society. 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 McCormack). However, in the reboot, they are revealed not to be married. For this role, he won the
Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series in 2005. He has also appeared in the films
The Guru (2002),
Shall We Dance? (2004),
Romance & Cigarettes (2005) and
Snakes on a Plane, 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. He appeared in
The Take (2007) as Agent Steve Perelli, alongside
John Leguizamo and
Tyrese Gibson. Cannavale serves as the voice of Corado R. 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 also read the
audiobook versions of
Richard Price's 2008 novel
Lush Life and Ed Falco's 2012 novel
The Family Corleone. On August 25, 2008,
ABC ordered his pilot
Cupid, a remake of the
1998 program which had starred
Jeremy Piven and
Paula Marshall, to series. In the new version of the series, Cannavale starred opposite
Sarah Paulson with script development overseen by original series creator
Rob Thomas.
Cupid premiered on March 31, 2009, but was cancelled by ABC after less than two months, on May 19, 2009. In 2008, he received a
Tony Award nomination for his role as Dennis in the
Broadway play,
Mauritius. In 2009,
CBS announced Cannavale would reprise his role of Det. Eddie Saccardo on the television show,
Cold Case, for three episodes, starting with the third episode of Season 7. Cannavale was in the film
The Other Guys (2010), and played the role of Terry Delfino in the film
Win Win (2011). He later starred in the Broadway play
The Motherfucker with the Hat alongside
Chris Rock and
Annabella Sciorra. On May 3, 2011 (his 41st birthday), he was nominated for a Tony Award for his leading role in that production. In 2012 and 2013, he guest-starred in the fourth and fifth seasons of
Showtime's
Nurse Jackie, for which he was nominated twice again for the Primetime Emmy Award for Outstanding Guest Actor in a Comedy Series in 2012 and 2013, as well as joining the cast of
HBO's
Boardwalk Empire, portraying the
psychopathic Sicilian gangster
Gyp Rosetti in the third season. 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.
TV Guide, in its "Cheers & Jeers 2012" issue, praised Cannavale for this "trifecta of great performances", commenting, "This guy is so good at playing bad, it's scary." He played what
Matt Zoller Seitz of
RogerEbert.com called a "heroically moving" lead role in
Danny Collins in 2015. Since 2015, Cannavale has been involved with voice-over work for Playing On Air, a non-profit organization that "records short plays [for public radio and podcast] written by top playwrights and performed by outstanding actors." He has starred in three short plays, including
Crazy Eights by
David Lindsay-Abaire, co-starring
Rosie Perez and
John Leguizamo;
Mere Mortals by
David Ives; and
2 Dads by
David Auburn. In January 2020, Cannavale appeared with his real-life partner
Rose Byrne in the play
Medea, written and directed by
Simon Stone. In 2021, Cannavale played Tony Hogburn in the
Nicole Kidman-led
Hulu miniseries
Nine Perfect Strangers (based on the
novel of the same name by
Liane Moriarty), which also featured
Melissa McCarthy,
Michael Shannon,
Luke Evans,
Samara Weaving, and
Asher Keddie. In 2022, Cannavale was seen portraying Dean Braddock in the 2022 Netflix series,
The Watcher. ==Personal life==