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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 of 425. Di Paolo had performed at the venue two years prior and wanted to return to produce a special there. The original promotional image for the special depicted Di Paolo giving the middle finger to a group of protesters, among them the murdered black activist Muhiyidin Moye. The image was criticised from some Twitter users; Di Paolo apologised, saying he did not realise it was Moye as it was chosen from a collection of stock photos. The artwork was then altered to depict a different protester. After two days, the video had amassed 125,000 views.

Di Paolo says he opposes political correctness, which he believes "ruined this country". Di Paolo was mentioned as part of a shock radio "brethren" in a New York Times article about CBS Radio's decision to fire Don Imus for referring to an African American college basketball player as a "nappy headed ho". The article described one of Di Paolo's bits in which he mocked an employee training manual entitled "Words Hurt and Harm", stating, "Right away, we’re starting with a false premise, because words don't hurt".

In March 2018, Di Paolo kicked off his nationwide Nick is Right Tour. On June 17, Di Paolo was punched by a female audience member after a gig at Levity Live in West Nyack, New York. While meeting fans outside the green room, her father had approached Di Paolo and informed him that his daughter "...wants to punch you in the face", during which she hit him below his left eye. Di Paolo contacted the police to file the incident and sought legal action.

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 home studio. The free stream is broadcast live on YouTube.

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 instalment 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. One post, sent on the anniversary of the Columbine High School massacre, urged future school shooters to attack universities that had liberal leanings. Di Paolo maintained that his "poorly worded tweet" should have resulted in a temporary suspension "at best", and that SiriusXM had overreacted.

In late 2016, Di Paolo filmed his second comedy special for Comedy Central, entitled Inflammatory. It was released on DVD and digital download in 2017.

During a 2015 interview on Marc Maron's WTF Podcast, Di Paolo described his political outlook as "center-right" (noting that he doesn't oppose abortion or gay rights) and mentioned that his friend Colin Quinn had once quipped, "you're not a political comedian, but you could tell a joke about McDonald's and everyone would know how you voted".

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 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.

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 as he wanted to "pursue some great opportunities". Lange continued to host the show with former professional American football player Jon Ritchie that was renamed The Artie Lange Show.

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.

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 assembled a demo tape and approached other radio stations in the city to host a morning show, but it was too difficult. He then took any fill in spots on the air when he could, including Jerry Doyle, Dennis Miller, and Dan Patrick. In January 2008, Di Paolo began an occasional online talk show on BlogTalkRadio.

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.

From 2002 to 2004, Di Paolo was a regular guest on the Comedy Central show Tough Crowd with Colin Quinn. He recalled that he was contracted to appear on the show twice a week, but after some early episodes he was called into a meeting due to his risque jokes about Jewish people. Quinn managed to convince the producers to keep Di Paolo as a guest. 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.

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 the first 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.

After returning to New York City in the early 2000s, Di Paolo moved into a condo in Tarrytown, New York. This was followed by a move to Westchester, New York in 2004. In April 2019, Di Paolo and his wife moved to Georgia.

Di Paolo's first comedy album, Born This Way, was released in 1999. It was recorded at The Comedy Store in La Jolla, California after the venue had become one of his favourite venues. Its title was suggested by comedian Colin Quinn.

In 1992, Di Paolo relocated to Los Angeles to further his career as "that's where the business is". While there he developed his stand-up act in local comedy clubs and took on several television and film roles, including a regular role as Tony, a bartender on the sitcom Grace Under Fire from 1994 to 1997. He went on to make an early appearance on national television on The Arsenio Hall Show and featured on HBO's special focused on up and coming comics. He returned to the University of Maine to perform stand-up at Damn Yankee, located above the student's union, around five years into his new career. 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 felt it took 12 years to find his voice through stand-up comedy, before he started to hone his act. From 1987 to 1992, he developed his act in 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.

After graduating Di Paolo landed several jobs, including office jobs in marketing and as a door-to-door salesman selling meat and seafood for Boston Gourmet. He recalled the job as fun and performed well, but felt burned out after two years. During this time, the stand-up comedy scene in the Boston area had picked up and a friend from university encouraged Di Paolo to go on stage as he regularly made his friends and colleagues laugh. Di Paolo was a fan of stand-up and was influenced by watching comedians appear on The Tonight Show with Johnny Carson, David Letterman on The Mike Douglas Show, Jay Leno on The Merv Griffin Show, and Robert Klein. He had wanted to have a go for several years but "didn't have the guts" but his lack of enjoyment as a salesman "led me to the stage". Di Paolo performed his first routine in the summer of 1986 at an open mic night at Stitches club in Boston, travelling from a family barbecue with "about 22 beers in me". He recalled his five-minute set went "pretty well" and wanted to pursue it full time, but his salesman job required a temporary relocation to Rhode Island. In the spring of 1987, he returned to Boston and started to make regular appearances at local open mic nights.

Di Paolo was born in Danvers, Massachusetts to parents Nick and Joan Di Paolo. In 1980, after graduating from high school, he attended the University of Maine where he became the running back of the university's football team and graduated in 1984 with a major in marketing. He said: "I cheated my way through with a 2.3" grade point average but picked this time as "the best years of my life". He joined the fraternity Sigma Nu. His brother also attended the university and did play-by-play commentary for the Maine Black Bears hockey team with Gary Thorne.

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.

Nicholas Rocco Di Paolo (born January 31, 1962) is an American stand-up comedian, writer, actor, radio personality and podcast host. In July 2018, he launched his new audio and video podcast, The Nick Di Paolo Show. He was also an emcee on truTV Presents: World’s Dumbest.