1980s–1990s From 1987 to 1992, he worked clubs in the New England area, including the Comedy Vault, the Comedy Connection, and Stitches. Two years in, he did his first gigs in
New York City which included a regular spot at
Catch a Rising Star. In his first year as a stand-up comic, he secured
Barry Katz as his manager and performed on over 300 nights. While there he developed his stand-up act in local comedy clubs and took on several television and film roles. In 2001, he and the team of writers were nominated for an
Emmy Award for Outstanding Writing for a Variety, Music, or Comedy Program. It was Di Paolo's second Emmy Award nomination. By 2001, Di Paolo had settled in Queens. He has done several Comics Come Home benefit shows. He left the station after management decided to change formats. He then took fill in spots on the air, including
Jerry Doyle,
Dennis Miller, and
Dan Patrick. Other television appearances include
The Colin Quinn Show on
NBC,
NewsRadio,
Suddenly Susan and
The Smoking Gun Presents. He has been a guest on radio shows, including
The Howard Stern Show,
Opie and Anthony, Di Paolo has done USO tours in Cuba and Japan. In 2008, he performed stand-up for US soldiers in
Afghanistan as a part of Operation Mirth, which Lange named and headlined. He was joined by
Gary Dell'Abate and
Dave Attell.
2010–2018 In April 2011, Di Paolo's special
Raw Nerve was released as part of the
Comedy Central Presents... series and on the television network
Showtime. In October 2011, Di Paolo launched a syndicated sports entertainment radio show with Lange named
The Nick & Artie Show. Di Paolo left in January 2013. Lange continued to host the show with former professional American football player
Jon Ritchie that was renamed
The Artie Lange Show. In October 2013, Di Paolo launched his weekly podcast,
The Nick Di Paolo Podcast, on the
Riotcast network. The weekly episodes were free while additional episodes were exclusive to his ConnectPal donators. Di Paolo was fired from SiriusXM after he posted comments on his Twitter account which read “School shooters, please confine yourself to coll. campuses, specifically faculty lounges at Berkeley, Fresno State etc.” Di Paolo was subsequently fired, to which Di Paolo responded that
Sirius XM had overreacted and his “poorly worded” tweet was only worth a suspension “at best”. In 2014, Di Paolo released his comedy special,
Another Senseless Killing. He wanted to film it in an intimate club setting and chose Acme in Minneapolis. In late 2016, Di Paolo filmed his comedy special entitled
Inflammatory. It was released on DVD and digital download in 2017. From May 15, 2017, to April 2018, Di Paolo hosted an evening radio show on the talk/comedy channel
Faction Talk on
Sirius XM Radio that aired from Monday through Thursday. In March 2018, Di Paolo kicked off his nationwide Nick is Right Tour.
The Nick Di Paolo Show On July 9, 2018, following Di Paolo's exit from
Sirius XM Radio, his launched his new audio and video podcast titled
The Nick Di Paolo Show. The one-hour show airs live four days a week from his private studio. The free stream is broadcast live on YouTube, author A.J. Rice, comedian
Colin Quinn, and
radio personality Anthony Cumia.
2019–present On May 6, 2019, Di Paolo released his one-hour comedy special,
A Breath of Fresh Air, for free on YouTube. He wanted to release it "without any media/industry filter" that networks such as
Netflix or
Comedy Central have in place, and his management aimed to present Di Paolo to a wider audience to increase his profile. It was filmed in February 2019 at the
Cohoes Music Hall in
Cohoes, New York in front of a sold-out crowd. Di Paolo had performed at the venue two years prior and wanted to return to produce a special there. Since 2021, Di Paolo has been a contributing writer for the
Fox News Channel's late night show
Gutfeld!, most often providing additional material for host
Greg Gutfeld and helping co-write the nightly opening monologues. In 2022, Di Paolo co-starred in the
Louis C.K. film
Fourth of July, playing the obnoxious uncle of
Joe List. In March 2023, Di Paolo joined the Mug Club network founded by
Steven Crowder, where he will be joined by
Alex Jones and
Bryan Callen. ==Personal life==