Did Portland Entrepreneur and Activist Jefferson Smith Pull Off the Greatest Political Prank Ever?

By Greg Grzesiak Greg Grzesiak has been verified by Muck Rack's editorial team
Published on September 22, 2023

Typically, there are two types of political pranks – those that make a point and those that nudge change. In 2008, then-Representative Jefferson Smith from Portland pulled off a stunt that accomplished both, making it one of the greatest political pranks of all time. 

The Rick Roll is perhaps the most pervasive prank of the Internet age, and Smith organized the greatest Rick Roll ever. For the uninitiated and unpranked, the “Rick Roll” is a harmless piece of email trickery where a friend sends you an urgent-sounding subject line, only to have it followed by a link to a video of Rick Astley singing his 1980s hit “Never Gonna Give You Up.” It’s a bit of fun that sends a simple message – I care about you.

In the context of a deadlocked legislative chamber – such as the “30-30” Oregon House of Representatives in Oregon some years back, with precisely thirty Republicans and thirty Democrats – the message “I care about you” can have bigger implications. 

Jefferson Smith and the Oregon House Rick Roll

In April 2011, Jefferson Smith came up with the idea of “Rick Rolling” the State House as a way to inject some levity and humor into politics. The State House consisted of thirty Democrats and thirty Republicans, and the prank was a bipartisan effort. The goal was to include lyrics from Rick Astley’s 1987 hit “Never Gonna Give You Up” in their speeches

“When I thought about the way the song was being used between friends,” Jefferson mused, “it seemed like a perfect message for politicians because it’s exactly what constituents need to know – that their elected officials actually care about them.” But for Smith, simply sending the message wasn’t enough. It had to be backed up with evidence. “And I could think of no better evidence,” Smith says with a glint of mischief, “than a broad demonstration of bipartisanship on the floor on the Legislative floor.” 

Smith’s Rick Roll redesign was clever. He asked representatives from both sides of the political aisle to work a specific lyric from the song into their written floor speeches while passing bills. The lyrics could then be lifted from the recorded speeches and edited together to create the first-ever bipartisan, political music video straight outta Oregon’s Capitol, set to the tune of “Never Gonna Give You Up.” 

“The key to success was having good-hearted and discreet representatives to ask,” Smith says gratefully. “There was a risk that if word got out to the wrong people, the idea would wither faster than a bill to tax puppy food.”

The lawmakers had to work the assigned lyrics into their speeches in a way that was relevant to their topic without asking for extra time.

Smith told Melissa Block of NPR that it took real effort from many people, particularly aides, to make this happen. However, it took little prodding to get other lawmakers to agree to do their part. Smith said that the video was released as an April Fool’s joke and that no tax dollars were used in the making of the clip. The video was intended as a mild break from much of what was being seen in national politics, and Smith hoped that if politicians could come together – to have fun and collaborate constructively, it could lead to positive change.

After weeks of recruitment, subterfuge, and all the political savvy he could muster, Smith finally released the video to a viral response. The Oregon House Rick Roll became global news – covered internationally by Time, CBS News, NPR, Yahoo News, Talking Points Memo, the BBC, The Huffington Post, and many many others… even Glamour. Mental Floss listed Epic Rick Rolls… and the Jefferson Smith Oregon House Rick Roll topped the list. 

Are there any lessons from the Oregon House Rick Roll? “Well, there might be some,” Smith says. “There’s more that brings us together than sometimes we remember. Even in a time of political brinksmanship, bipartisanship and community are still possible. And humor is a helpful tool for getting that done.” 

And this, according to Smith’s “second law of legislative thermodynamics” (he did not offer a first law): “the attention something gets is often inversely proportional to its importance.”  

“It’s obviously a little silly thing,” he admitted then. “But even just having a little fun together helped develop some professional relationships. Just a tiny spoonful of sugar to let the political medicine go down, so to speak.”

By Greg Grzesiak Greg Grzesiak has been verified by Muck Rack's editorial team

Greg Grzesiak is an Entrepreneur-In-Residence and Columnist at Grit Daily. As CEO of Grzesiak Growth LLC, Greg dedicates his time to helping CEOs influencers and entrepreneurs make the appearances that will grow their following in their reach globally. Over the years he has built strong partnerships with high profile educators and influencers in Youtube and traditional finance space. Greg is a University of Florida graduate with years of experience in marketing and journalism.

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