[6] While working as a stand-in on numerous movies in the 1980s, he had 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.

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.

Along with comedian friends Arj Barker and Tony Camin, Benson co-created and performed in the comedy stage-show The Marijuana-Logues.

Benson aims to record a new album every April 20 (with a subsequent summer release date) for as many consecutive years as possible.

A regular feature of the podcast is the Leonard Maltin Game, which has been described as Name That Tune with movies instead of songs.

Other regular features of the podcast include the segments Tweet Relief: Tweets About Movies, Watch This/Not That, Not for Emetophobes, and From the Corrections Department, as well as the games Build a Title, Name a Movie, A-B-C-Deez Nuts, How Much Did This Shit Make?, Lincoln or Bane?, Love, Like, Hate, Hate-Like, Doing Lines with Mark Wahlberg, Last Man Stanton, Whose Tagline Is It Anyway, Now Buscemi Now You Don't, Tell The Truth!, Live Die Repeat, Alex and Jason and Deb's IMDB game, and F Marry Kill: Movies.

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.

Bang!, The Joe Rogan Experience, WTF with Marc Maron, The Adam Carolla Show, Nerdist with Chris Hardwick, Mohr Stories, You Made It Weird with Pete Holmes, Never Not Funny, and Who Charted with Howard Kremer and Kulap Vilaysack.

The show was based on the live stand-up comedy showcase of the same name that he had hosted in Los Angeles for many years.

From 2013 to 2019, Benson hosted a weekly talk show on YouTube titled Getting Doug with High, which generally aired live every Wednesday at 4:15 PM PST.

He asked them questions and discussed topics (usually related to marijuana), and at the end of the show, he made them watch a magic trick.

Occasionally, the show was done in front of a live audience in Los Angeles, where the performers took turns inhaling from bags of vaporized cannabis.

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

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.

[18] "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.

"[18] The segment drew wide attention and outrage in Canada after being posted on YouTube following the reported deaths of four Canadian soldiers in Afghanistan three days earlier.

[19][20][21] Canada, at the time, had been in command of the NATO mission in the Kandahar Province, the birthplace and former Taliban capital, for the past three years.

"[23] Canadian Defence Minister Peter MacKay called on Fox to apologize for the satirical comments, describing the remarks as "despicable, hurtful and ignorant.