Leary began working as a comedian at the Boston underground club Play It Again Sam's. His first real gig was at the Rascals Comedy Club as part of the TV show
The Rascals Comedy Hour, on October 18, 1990. Leary wrote and appeared on a local comedy series, ''Lenny Clarke's Late Show
, hosted by his friend Lenny Clarke and written by Martin Olson. Leary and Clarke both spoke about their early affiliations and influences in the Boston comedy scene in the documentary film When Standup Stood Out'' (2006). During Leary's time as a Boston-area stand-up comic, he developed his stage persona. Leary appeared in sketches on the
MTV game show
Remote Control, playing characters such as
Keith Richards, co-host
Colin Quinn's brother and artist
Andy Warhol. He earned fame when he ranted about
R.E.M. in an early 1990s MTV sketch. Several other commercials for MTV quickly followed, in which Leary would rant at high speeds about a variety of topics, playing off the then-popular and growing
alternative scene. One of these rants served as an introduction to the video for "Shamrocks and Shenanigans (Boom Shalock Lock Boom)" by
House of Pain. Leary released two records of his comedy:
No Cure for Cancer (1993) and ''
Lock 'n Load (1997). In late 2004, he released the EP Merry F %$in' Christmas, which included a mix of new music, previously unreleased recordings and some tracks from Lock 'n Load''. In 1993, Leary's
sardonic song "
Asshole", about the stereotypical American male, achieved much notoriety. The song was voted No. 1 on the
Triple J Hottest 100 poll of
1993. and was used in
Holsten Pils ads in the UK, with Leary's participation, and with adapted lyrics criticizing a drunk driver. The single was a minor hit there, peaking at No. 58 in the
UK Singles Chart in January 1996. In 1995, Leary was asked by
Boston Bruins legend
Cam Neely to help orchestrate a Boston-based comedy benefit show for Neely's cancer charity; this became
Comics Come Home, which Leary has hosted annually ever since. and
Ralph Fiennes at a U2 concert in Madison Square Garden, October 2005 Leary has appeared in many films, including
The Sandlot (1993) (as Scott's stepfather Bill),
Demolition Man (1993) (as an
Emmanuel Goldstein-esque revolutionary to
Nigel Hawthorne's
Big Brother),
Judgment Night (1993),
The Ref (1994),
Gunmen (1994),
Operation Dumbo Drop (1995),
Wag the Dog (1997),
Suicide Kings (1997),
The Matchmaker (1997),
Monument Ave. (1998),
The Thomas Crown Affair (1999)
Dawg (2002), and
Draft Day (2014). He had a role in
Oliver Stone's
Natural Born Killers (1994) that was eventually cut. He held the lead role in two television series,
The Job and
Rescue Me. He co-created the latter, in which he played
Tommy Gavin, a New York City firefighter dealing with alcoholism, family dysfunction and other issues in post-
9/11 New York City. Leary received
Emmy Award nominations in 2006 and 2007 for Outstanding Lead Actor in a Drama Series for
Rescue Me, and in 2008 for Outstanding Supporting Actor in a Miniseries or a Movie for the HBO movie
Recount. Leary was offered the role of Dignam in
The Departed (2006) but turned it down because of scheduling conflicts with
Rescue Me. He provided voices for characters in animated films, such as a fire-breathing dragon named Flame in the series
The Agents, a pugnacious ladybug named
Francis in ''
A Bug's Life (1998) and a prehistoric saber-toothed tiger named Diego in the Ice Age'' film series. He has produced numerous movies, television shows, and specials through his production company, Apostle; these include
Comedy Central's ''
Shorties Watchin' Shorties, the stand-up special Denis Leary's Merry F#$%in' Christmas
and the movie Blow'' (2001). As a
Boston Red Sox fan, Leary narrated the official
2004 World Series film. In 2006, Leary and Lenny Clarke appeared on television during a Red Sox telecast and, upon realizing that Red Sox first baseman
Kevin Youkilis is Jewish, delivered a criticism of
Mel Gibson's antisemitic comments. As an
ice hockey fan, Leary hosted the
National Hockey League video ''NHL's Greatest Goals
. In 2003, he was the subject of the Comedy Central Roast of Denis Leary''. Leary did the TV voiceover for
MLB 2K8 advertisements, using his trademark rant style in baseball terms, and ads for the 2009
Ford F-150 pickup truck. He has also appeared in commercials for
Hulu and
DirecTV's
NFL Sunday Ticket package. Leary was a producer of the
Fox series ''
Canterbury's Law, and wrote and directed its pilot episode. Canterbury's Law
aired in the spring of 2008 and was canceled after eight episodes. On September 9, 2008, Leary hosted the sixth annual Fashion Rocks event, which aired on CBS. In December of the year, he appeared in a video on funnyordie.com critiquing a list of some of his "best" films, titled "Denis Leary Remembers Denis Leary Movies". Also in 2008, Leary voiced a guest role as himself in The Simpsons'' episode "
Lost Verizon". On March 21, 2009, Leary began the Rescue Me Comedy Tour in
Atlantic City, New Jersey. The 11-date tour, featuring
Rescue Me co-stars Lenny Clarke and
Adam Ferrara, was Leary's first stand-up comedy tour in 12 years. The
Comedy Central special
Douchebags and Donuts, filmed during the tour, debuted on American television on January 16, 2011, with a DVD release on January 18, 2011. in 2017 Leary played
Captain George Stacy in the movie
The Amazing Spider-Man, released in July 2012. He wrote the
American adaptation of
Sirens. Leary is an executive producer of the documentary
Burn, which chronicles the struggles of the
Detroit Fire Department.
Burn won the 2012
Tribeca Film Festival Audience Award. Leary created a television series for FX called
Sex & Drugs & Rock & Roll, taking the starring role himself. A 10-episode first season was ordered by FX, with the premiere on July 16, 2015. The show ran for two seasons. In 2022, Leary was cast in the recurring role of Frank Donnelly, an NYPD officer on
Law & Order: Organized Crime. Leary has been the narrator for
NESN's documentary show about the Boston Bruins called
Behind the B since the show began in 2013. ==Personal life==