Nick Di Paolo

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Di Paolo said it took years to hone his stand-up act. 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. He described his act during this early period as "a rapid fire approach, four or five punches attached to every joke". Upon moving to New York City, Di Paolo's act became more political from reading local newspapers and comparing views of each publication. In his first year as a stand-up comic, he secured Barry Katz as his manager and performed on over 300 nights. Di Paolo went on to live in New York City with comedian Louis C.K. as his roommate.

In 1992, Di Paolo relocated to Los Angeles. While there he developed his stand-up act in local comedy clubs and took on several television and film roles. He went on to make an early appearance on national television on The Arsenio Hall Show and featured on HBO's Young Comedian's Special, which focused on up and coming comics. While in Los Angeles, Di Paolo befriended comedian and actor Artie Lange during an audition for a pilot that had Lange play the lead.

Di Paolo's first stand-up album, Born This Way, was released in 1999 and was recorded at The Comedy Store in La Jolla, California. Its title was suggested by comedian Colin Quinn.

After five years in Los Angeles, Di Paolo had considered returning to New York City when Chris Rock offered him a writing position on The Chris Rock Show which was based in the city. He accepted, and wrote for two seasons. 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. He looked back at his time on the show as one of the best times of his career and went on to work contributing to comedy scripts. By 2001, Di Paolo had settled in Queens.

In June 2001, Di Paolo made his first appearance on Late Show with David Letterman and later, filmed promos for the Comedy Central roast of Hugh Hefner. His appearances on The Howard Stern Show soon after led to comedy gigs nationwide with various staff from the show, including Stuttering John and Artie Lange, which further raised his profile.

From 2002 to 2004, Di Paolo was a regular guest on the Comedy Central show Tough Crowd with Colin Quinn. He has appeared on several roasts for the network, including The Comedy Central Roast of Pamela Anderson, The Comedy Central Roast of Denis Leary, The Comedy Central Roast of Jeff Foxworthy and The Comedy Central Roast of Larry the Cable Guy.

In 2004, Di Paolo released his second comedy album, Road Rage. Like his first, it was titled by Quinn. Also that year, he starred in Shorties Watchin' Shorties, an animated comedy series on Comedy Central, alongside Patrice O'Neal. They voice two unsupervised babies who comment on television clips, including performances by fellow stand-up comics. The idea originated from Di Paolo after the network wanted the pair to work together. He has done several Comics Come Home benefit shows.

He was cast as a police officer in Artie Lange's feature film Artie Lange's Beer League and in The Sopranos. He also wrote for the 77th Academy Awards and the MTV Video Music Awards.

From December 2006 to December 2007, Di Paolo hosted an afternoon radio show on WFNY in New York City. 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. In January 2008, Di Paolo began an occasional online talk show on BlogTalkRadio.

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, and The Dennis Miller Show.

He was cast as the building superintendent on Louis C.K.'s HBO show Lucky Louie, and appeared with a recurring role in Louis C.K.'s FX series Louie.

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.

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. The podcast ended in April 2018 following his firing from SiriusXM, after 226 episodes. 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. Excerpts from the show were released as a weekly installment of his podcast, The Nick Di Paolo Podcast. The show was cancelled after Di Paolo had posted comments on his Twitter account that management deemed offensive, and was subsequently fired. Di Paolo maintained that his "poorly worded tweet" should have resulted in a temporary suspension "at best", and that SiriusXM had overreacted.

In March 2018, Di Paolo kicked off his nationwide Nick is Right Tour.

On July 9, 2018, Di Paolo launched his new audio and video podcast, 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. 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.

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