Black describes his political affiliation as such: "I'm a socialist, so that puts me totally outside any concept ... the Canadians get it. But seriously, most people don't get it. The idea of capping people's income just scares people. 'Oh, you're taking money from the rich.' Ooh, what a horrifying thing. These people really need $200 million".
In 1998, he starred in his first comedy special on the series Comedy Central Presents. He starred in two additional episodes of the series in 2000 and 2002. He starred in another special for the network in 2002 titled Taxed Beyond Belief.
In 2000, Black and fellow comedian Jim Norton were arrested for their involvement with "The Naked Teen Voyeur Bus", a specially designed bus with acrylic glass walls containing numerous (18 and 19 year old) "teen girls." This bus rode around Manhattan while being broadcast on the "Opie and Anthony" radio show. Unfortunately, radio station management did not inform the O&A show that the bus' route was also the route that President Clinton was taking that same day. Twenty-eight hours after the arrest, Black and Norton were released. Black appeared on The Daily Show the following night where he stated he was exercising his constitutional rights. He then joked that the location of this particular right was unclear, but that it was "between 'all men are created equal' and 'don't shit where you eat.'" Additionally, at a fundraising event for New York Attorney General candidate Mark Green on June 28 2006, Black talked about how he was unable to attend a previous fundraising event for Green because the arrest occurred shortly before.
In 2004, he had an HBO stand-up special titled Black on Broadway. That same year Black appeared in an episode of Law & Order: Special Victims Unit as a shock jock. He also released his autobiography, Nothing's Sacred, in 2005. Since November 9 2005, Black has been making appearances in small segments on The Weather Channel. In December 2005, he appeared in an animated holiday special The Happy Elf, as the voice of the extremely tightly wound elf, Norbert.
Black was the voice of "Manobrain" during the third season of the Cartoon Network series "Duck Dodgers". He was the inventor of a diet pill which was stolen while he was in college. He blamed the theft on his college friend Dr. I. Q. High, not realizing that the actual thief was Duck Dodgers. The theft set Manobrain on the path of evil.
Lewis Black played the character of the Deadly Duplicator in Harvey Birdman: Attorney at Law, on Adult Swim. He appeared in four episodes before the show ended. He played the part once more in the Harvey Birdman: Attorney at Law video game.
On April 21 2006 Lewis performed at the Warner Theatre in Washington, DC for an HBO special, Red, White, and Screwed. It aired on June 10 2006, and a DVD was released October 3 2006. When explaining his choice of venue, Black states that "some asshole" was paid to count the number of uses of the word "fuck" from his previous HBO special, Black On Broadway, and that the original location, the Kennedy Center, wanted him to cut back on its use. Black was told the number was 42, when actually it was approximately 78.
In the film Accepted, a film about high school graduates who create a college when they fail to get accepted into any, he plays Dean Ben Lewis of the school "South Harmon Institute of Technology" or S.H.I.T.; as the Dean, he talks about his views of the world. He also appears in the 2006 films Man of the Year and Unaccompanied Minors. Black hosted Comedy Central's Last Laugh '06, which aired on December 10 2006.
On June 18 2007 he sat in with Southern rock/Jam band Gov't Mule at the 6th annual Bonnaroo music festival, where he had performed earlier that weekend, for what was to be a quick joke. A member of the audience threw a bottle at Lewis, which struck him. Black was upset and he encouraged the audience to boo the heckler before leaving the stage in disgust, while shouting obscenities at the heckler. This act was seen in an episode of "Lewis Black's Root of All Evil" titled "YouTube vs. Porn".
On June 29 2007 Lewis gave a benefit show at Springbrook High School, his alma mater, in the school's auditorium for 1,100 alumni, faculty, and students. Black performed in his usual style, stopping at points to remark how good it felt to use that language on that particular stage. At the end of the show he was given a Springbrook football jersey, and cursed at one teacher for giving him a B and causing him not to graduate first in his class.
Lewis Black did the voice-over for an oxpecker named Ted in Cartoon Network series My Gym Partner's a Monkey, appearing in "Hornbill and Ted's Bogus Journey." The character is portrayed in the same fashion as his comedy shows, though without the profanity. In addition, the bird's clothes, looks, and mannerisms match those of Black himself.
On October 5 2007, It was announced by Comedy Central that Lewis Black will be the host of his own television series in March 2008. The show, titled The Root Of All Evil, will pit two people or pop-culture topics against each other as a panel of comedians argue which is more evil, e.g., "Paris Hilton vs. Dick Cheney" and "Internet Porn vs. YouTube". At the end of the argument Lewis Black will make the final decision as to which is more evil.
In mid December 2007, Black went with Robin Williams, Kid Rock, Lance Armstrong and Rachel Smith "Miss USA 2007" on a USO trip to support the troops in Iraq and Kuwait. They then wrapped it up on Dec 22nd at the U.S Naval Station in Rota, Spain.
On February 18, 2008, Black hosted "History of the Joke, with Lewis Black", a 2-hour comedy-documentary on The History Channel.
Black is currently on tour touting his latest book Me of Little Faith. He appeared in Washington, DC at the historic 6th and I Synagogue on June 10, 2008 to a sellout audience. He is also currently doing a stand-up tour called Let Them Eat Cake.