Doug Benson

At the conclusion of many of the early podcasts, Doug would state "As always, Willem Dafoe is a Shithead," which resulted in so many people wondering about why, that Google searches began to automatically complete the phrase as a suggested match. The Willem Dafoe comment started as a joke based on the fact that it would seemingly be the only bad words ever uttered about Dafoe, but many people didn't catch on and, after explaining it a few times, Benson decided to let Dafoe rest. Until 2019, the runners up in the Leonard Maltin game are allowed to name one shithead as a consolation prize. Starting in early 2019, Benson now closes the show with "Positive Energy" in honor of his late friend, Brody Stevens

Benson starred as the judge on The High Court with Doug Benson, a comedic court show on Comedy Central. During each episode Benson is under the influence of cannabis. All of the cases featured are real and all of his rulings are real and legally binding. The series premiered on February 28, 2017. After hearing the case with his guest bailiff, Judge Doug and the bailiff retire to his chambers where they smoke marijuana while deciding the case. Special guest bailiffs for the series include comedians Tiffany Haddish, Michael Ian Black, Reggie Watts, Todd Glass, Rory Scovel, Brandon Wardell, and others. The series is produced by JASH and Propagate Content.

Benson regularly appears as a panelist on the Comedy Central program @midnight, and during the week of January 4–7, 2016, was featured during a weeklong special titled the "Benson Bowl," featuring many marijuana-related games. Benson currently ranks first in number of appearances on the show, as well as victories.

Canadian Defence Minister Peter MacKay called on Fox to apologize for the satirical comments, describing the remarks as "despicable, hurtful and ignorant." Benson was scheduled to appear in Canada at Edmonton's The Comic Strip April 3–5, 2009, but the shows were canceled after the owner received threats of "bodily injury" toward the American comic. "Some were saying he wouldn't make it from the airport to the club. For everyone's safety, we decided it was best to avoid the scenario altogether," said manager Rick Bronson. Benson offered an apology following the incident on CTV News Power Play with Tom Clark. The comedian stated that he was "ignorant about the situation in Afghanistan" and that the timing of the jokes were "completely out of line". "I honestly said things, in retrospect, I completely regret" said Benson and he has vowed to "never appear on the show again".

The show spun off into a monthly audio-only podcast on January 21, 2011, which took the TV show's format and altered it slightly by allowing the performances and conversations to play out in longer unedited episodes.

In 2010, Benson started an annual, 2 hour Twelve Guests of Christmas special every holiday season. This episode features 12 guests (occasionally more) rather than the usual 3 guests and they play an elimination style Leonard Maltin Game. Scott Aukerman won the first year, while Graham Elwood dominated the next two years in a row. The 2013 champion was podcast fan and Pardcast-A-Thon auction winner, Sean Sakimae. Sakimae also qualified for the next Tournament of Champions for naming the film Titanic in negative names and winning the game. Riki Lindhome beat Jimmy Pardo in the finals of the 2014 edition when Pardo couldn't get the name Lori Singer when going negative three on Footloose. Scott Aukerman bested Sarah Silverman for his second win in 2015.

On November 5, 2010 Comedy Central began airing The Benson Interruption, hosted by Benson. The show is based on the live stand-up comedy showcase of the same name that he has hosted in Los Angeles for many years. Special guests for the series include comedians Chris Hardwick, Patton Oswalt, Brian Posehn, Adam Carolla, Nick Swardson, Rob Huebel, Nick Kroll, Thomas Lennon, Mary Lynn Rajskub and Eugene Mirman.

On August 4, 2009, Benson's second album, Unbalanced Load, was released by Comedy Central Records. His third album, Hypocritical Oaf was released on August 31, 2010. Benson aims to record a new album every April 20 (with a subsequent summer release date) for as many consecutive years as possible. Benson's fourth album, Potty Mouth, was released on August 29, 2011. The pattern continued with the release of his fifth album, Smug Life, which was released on July 3, 2012, and Gateway Doug, his sixth album, released on July 9, 2013. On July 8, 2014, Doug released a sequel to Gateway Doug entitled Gateway Doug 2: Forced Fun. His latest album release is Promotional Tool which came out on June 9, 2015.

On December 29, 2009, Benson had a documentary special called The High Road with Doug Benson air on the G4 network. The special followed Benson and comedian Graham Elwood on one of their stand-up comedy tours.

On March 17, 2009, the host of the Fox News comedy program Red Eye w/ Greg Gutfeld along with Benson as a panelist, joked about Canadian Lieutenant General Andrew Leslie's statement that the Canadian Armed Forces may require a one-year "synchronized break" once Canada's mission in Afghanistan ends in 2011. "Meaning, the Canadian military wants to take a breather to do some yoga, paint landscapes, run on the beach in gorgeous white Capri pants," Gutfeld said. "I didn't even know they were in the war", added Benson, then continued, "I thought that's where you go if you don't want to fight. Go chill in Canada." Gutfeld also said: "Isn't this the perfect time to invade this ridiculous country? They have no army!"

In 2008, Benson was the protagonist of the film Super High Me (a play on the name and concept of the film Super Size Me), released on DVD on June 10, 2008. In the movie, Benson compares the results of not smoking any marijuana at all for 30 days versus the effects of smoking as much marijuana as possible for the same amount of time. The film was produced by Red Envelope Entertainment. The results of the experiment were that it had little or no negative effects on Doug's health. Doug is currently suing the people who made the original film to stop a sequel.

In 2007, he starred in the film Super High Me, a documentary about marijuana usage. Benson also currently hosts the popular Doug Loves Movies podcast along with his weekly marijuana video podcast show Getting Doug with High. His Comedy Central series The Benson Interruption ended its first season in December 2010 and was turned into a monthly podcast in January 2011.

In 2007, Benson was a contestant on fifth season of the NBC reality show Last Comic Standing. He was voted off the program during the ninth episode, earning him 6th place overall.

In 2006, Benson began hosting a weekly comedy podcast, titled Doug Loves Movies (formerly I Love Movies with Doug Benson), which is recorded in front of a live audience at the Upright Citizens Brigade Theatre in Los Angeles. The show typically tapes weekly, and is later archived on iTunes for fans to listen to for free. Benson and guests talk about movies and comedy both. Benson's guests have included such notables as Daniel Van Kirk as Mark Wahlberg, John Lithgow, Leonard Maltin, Brian Posehn, Joe Rogan, Zach Galifianakis, Sarah Silverman, Patton Oswalt, Jon Hamm, Adam Carolla, David Cross, Bob Odenkirk, Scott Aukerman, Adam Scott, Ron Bennington, Aziz Ansari, Amy Poehler, Wayne Federman, Elisabeth Shue, Aubrey Plaza, Michael Cera, Edgar Wright, Paul F. Tompkins, T.J. Miller, Kumail Nanjiani, Gillian Jacobs, Michael Sheen.

In the 2000s, the comedian regularly appeared on the VH1 show Best Week Ever and taped several episodes of Comedy Central Presents.

In the mid to late 1990s, Benson had small roles on HBO's Mr. Show with Bob and David, which was co-created by his friend David Cross. He also had small roles on Curb Your Enthusiasm, How I Met Your Mother, The Sarah Silverman Program, Yes, Dear, and Friends.

While in Los Angeles, Benson began doing stand-up after he and two other friends dared each other to. One of them didn't show, and the other one signed up too late. Benson claimed that "I went in anyway and did my three minutes of whatever I could come with and people actually laughed." At the age of 22, Benson began performing regularly as a stand-up comedian; however, it wasn't until 28 that he became a stoner, after a week's worth of gigs smoking pot afterwards alongside Brian Posehn and Greg Proops. He made his earliest television appearances as a stand-up in the late 1980s and early 1990s on programs such as Comedy Central's The A-List and Two Drink Minimum and was one of the featured comedians in the cast of Joel Hodgson's sketch-comedy pilot The TV Wheel which aired on Comedy Central in 1995. One of Benson's earliest jobs in television was writing for the MTV game-show Trashed in 1994.

While working as a stand-in on numerous movies in the 1980s, he had visible roles as an extra in films such as Blade Runner, Fast Times at Ridgemont High, About Last Night and a backup dancer in the Disney theme park attraction Captain EO.

Douglas Steven Benson (born July 2, 1962) is an American comedian, marijuana rights advocate, television host, actor and reality-show judge who has appeared on Getting Doug With High, Comedy Central Presents, Best Week Ever, and Trailer Park Boys, and was a contestant on Last Comic Standing in the show's fifth season. He served as a judge for the Comedy Central series The High Court with Doug Benson.