May 20, 2022

Cannabis, Comedy, and a Catalyst for Change: Billy Anderson and The Gateway Show

May 20, 2022
The Gateway Show

Comedy and cannabis are a natural fit.  But, how can a marriage between cannabis and comedy make for one of the best overall entertainment experiences ever, and also be a vehicle for lifting the social stigma surrounding the cannabis plant? Enter The Gateway Show and, the mastermind behind it, Billy Anderson.

What is The Gateway Show?

The Gateway Show has a simple yet uniquely creative and highly (pun intended) effective concept: bring comedians on stage to perform, take an intermission to get them stoned, and then bring them back on stage for another set in their stoned state.  This concept, along with a name that is a play-on about cannabis being a “gateway” drug, started 7 years ago and has grown in popularity ever since, giving way for great entertainment and giggles to stoners and non-stoners alike, proving that cannabis can yet again can enhance an experience.  

Billy Anderson performing with fellow comics at a recent Gateway Show in Portland, Oregon.

When Billy Anderson first started The Gateway Show in Seattle in February of 2015, he was simply trying to expand his platform as a comedian, and saw cannabis legalization as a means to try something new that people might like.  Well, he got more than he bargained for as the show has now expanded across the country, created opportunities for comedians, spectators, and cannabis companies, survived a time where venues were basically decommissioned for almost 2 years, and has grown in the size of it’s platform and popularity ever since.  

Anderson is now based in Los Angeles, but when I first met him in 2017, he was having a great deal of success with the show already, and proving time and time again that people were interested in this concept because of the way it served as both entertainment and a platform to essentially normalize (and make light of) cannabis use.  However, there has been an incredible amount of progress and growth for The Gateway Show over the last 5 years, despite the entertainment industry being shut down for almost 2 of those years due to a global pandemic. 

Billy Anderson and The Gateway Show

Billy Anderson is the founder and host of The Gateway Show.

Anderson told me that he was doing shows as late as March of 2020, when the pandemic essentially shut things down for anyone doing live performances.  While he worked hard to keep the show afloat, performing in venues that would only allow for one-third of their regular capacity, digital/online shows for people to enjoy, and even a daily livestream on Facebook, it simply wasn’t the same.  After trying his best, Anderson stopped doing any shows at all for about a year and a half.  However, he was able to benefit from a federal pandemic-related support grant and that is what allowed him to bring The Gateway Show back on stage for live audiences.  His first comeback show was at the Bossanova Ballroom in Portland, Oregon in September of 2021.  That show and the ones that followed were not only well received but also proved to be profitable for Anderson and the comics he hired.  He has previously worked with Funhouse Lounge in Portland and then moved onto bigger venues (like Bossanova) because people were so receptive to the show and interest had grown so much.  

By the end of June in 2021, Anderson was producing shows in Los Angeles. From there he expanded to Montana, Massachusetts, Florida (even in Key West), and New Mexico.  Anderson said, “I am just now where I wanted to be in April of 2020, but I also have a newfound energy and dedication to keeping the show going.” He said that Seattle is the best example of how to explain the growth of the show…in the beginning days of the show, he used to do one show a month with approximately 60 people in the audience.  Now, he consistently sells out a 300 seat venue in the same city with no sign of slowing down. 

The Gateway Comedy Show: a 420 Experience

Portland, Sacramento, and Seattle feel like Anderson’s home bases for The Gateway Show, as those were the first areas that the show took off.  Anderson now does 2 shows back to back in Sacramento because the size of the venue doesn’t allow for a large enough audience compared to other venues, and both of those shows also consistently sell out.  When asked, “What is the limit for The Gateway Show?” Anderson responded, “I am not exactly sure…if we did a 500 person theater, would the show be the same? Also, I really rally for paying comics a profitable wage and want to be able to do more for them, like get photos and film crews so they can benefit them and their personal platforms.”

Mike Masilotti is a comedian who has known Anderson since 2013.  “Billy would never book me for The Gateway Show to begin with because I am a daily smoker. After many conversations, Billy finally believed me and agreed to let me be one of the comedians in the show.”

Masilotti started touring with Anderson in 2018 and has now hosted 4-5 Gateway Shows and participated in over 50.

“I love seeing what Billy is doing.  The more states I go to the more I realize what a good thing he has going on. He pays his comics well and works his butt off. It is amazing to see how much effort and intention he puts into the show.  He could easily focus on headlining and he doesn’t,” Masilotti commented.  

Both Anderson and Masilotti agree that The Gateway Show’s crowds are different (in a good way). “They aren’t dressing up in weed clothes or super stoners, but instead are usually young professionals who are successful stoners. The show does not feel super stoney, and we try to keep it more in the realm of normalizing weed for consumers.  The crowd is right there with you and excited for the experience. As a performer it makes me take way bigger chances.  I don’t do any scripted material for my stoned set, I just bounce off the crowd and their energy and it helps me so much as a comedian.  They know you’re high and they (often) are too, so they are with you,” Masilotti explained. 

Following the release of “America’s Sweetheart”, Billy Anderson has most recently dropped his debut comedy album “Live from Augusta.”

As far as other current projects and future endeavors, Anderson hopes to film a pilot stand-up comedy travel log based around cannabis. He is also in talks with Church of Cannabis in Denver for filming and doing some cannabis oriented tours, education, and shopping with commentary about what the cannabis culture in the city is like.

Regardless of what he’s up to next, it is clear that Billy Anderson is not slowing down any time soon, so keep an eye out for The Gateway Show coming to a city near you, and know that this is just one more piece to helping normalize cannabis use and change public opinion surrounding the plant we all know and love so much. 


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