Jack McNamara's entered a Pit Viper VHS contest and won sweet shades; his ambition didn't end there. Credit: Jack McNamara

New York copywriter Jack McNamara likes a challenge — the more oddball, the better.

And the proof of his scrappiness is now showcased among the shelves of the world’s last standing Blockbuster Video, right here in Bend.

Sometime in March, the freelance advertising copy director and marathon runner learned that popular retro sunglass company Pit Viper only reviewed “Sponsor-Me” pleas in VHS format — a 5-minute video on a literal videotape cassette.

McNamara was down to get creative.

Training in preparation for the Sydney Marathon on Aug. 30, McNamara, who’s 39 and lives in Harlem, wondered: Would Pit Viper sponsor me?

After all, he’s running the marathon less for glory than for charity (proceeds benefit the We Run Foundation). He previously tackled the Boston Marathon, where he earned $12,000 for a separate nonprofit involved with stroke research.

The result of several months’ collaboration with a production team, “Jack’s Pit Viper Tape” is a 5-minute video that plays on one of McNamara’s websites and feels like clicking through ‘90s basic television channels. With a background in improv comedy hosting, McNamara acts out various characters, such as pseudo-scientist Dr. Marty Thong; a Shopping Network host; and race-medal festooned alter-ego “Jake McNamara” to sell Pit Viper on adding him to its sponsored athlete roster.

And don’t forget McNamara’s fight scene with a kangaroo.

Even New Yorkers love Pit Viper. Copywriter Jake McNamara made a 5-minute Australia-themed Pit Viper video, which he delivered in VHS, to both the shades company and Blockbuster. Credit: Jake McNamara

Delightfully, McNamara’s video is viewable online through a wood-paneled TV player, like the ones you remember from sleepover parties in your parents’ semi-furnished basement. Adjust the VCR clock and — jokes on you. Eject “The Pit Viper VHS” and cue up the 8-bit-styled video game “Viper Sniper,” McNamara’s riff on Nintendo’s “Duck Hunt.” (This reporter clocked 25 viper kills before returning to work; McNamara swears the game is winnable and that the payoff is very Pit Viper-y.)

McNamara gathered inspiration for a vintage-y video that would dovetail with Pit Viper’s messaging: “Due to a high volume of weak-a*s proposals,” reads the company’s submission page, “Pit Viper is now ONLY accepting physical Sponsor Me tapes.”

McNamara recalled the shakily captured skateboard videos and endearingly schlocky local TV commercials he loved as a kid in the ‘90s.

Also high up on his inspiration board: the absurdist comedy of Tim Heidecker and Eric Wareheim. The frequent collaborators are known not just for analog-parodying Adult Swim shows, “Tom Goes to the Mayor” or “Awesome Show, Great Job!,” for example, but their wacky ad campaign for Absolut Vodka that also starred Zach Galifianakis. (You just have to watch them.)

“That [kind of comedy] is very much Pit Viper’s sense of humor,” McNamara said.

McNamara was further inspired by Pit Viper’s sample submission video, which features two overland truckin’ baddies spitting seltzer, throwing devil’s horns and cajoling Pit Viper for truck rally entry-fee cash.

McNamara’s gambit worked. Pit Viper reps told him his video was “awesome” and mailed him some free specs and swag to run in during the Sydney Marathon.

Harlemite Jack McNamara traveled from NYC to Bend to deliver a retro, Pit Viper-themed VHS to the
last Blockbuster in this galaxy — and, most scientists agree — the entire third dimension known
to humankind. Credit: Jake McNamara

“I’m wearing a Pit Viper t-shirt as we speak,” he added.

But will McNamara go from the “flow-gram” to being an official Pit Viper teammate, which includes the likes strongman Caleb Francis, pro snowboarder Hana Beaman or the human skateboard obstacle Manramp?

Pit Viper told McNamara they’ll make official sponsorship decisions in October.

Meanwhile, snail-mailing a VHS to Pit Viper wasn’t enough for McNamara, who grew up visiting Blockbusters in his native Boston. He hoped to place a physical copy of “Jack’s Pit Viper Tape” in the last remaining Blockbuster. He called up the video store on NE Revere Avenue in Bend, trying to get ahold of Sandi Harding, the general manager who’s become a niche celebrity for keeping Blockbuster’s lights on. He wanted to know if he could hand-deliver a copy for inclusion on its shelves.

“For me, the last Blockbuster is where all VHS deserves to be,” McNamara said.

Source film critic Jared Rasic visited the last Blockbuster in August 2025. The iconic store has become a destination for school field trips and filmmakers alike. Credit: Jared Rasic

Harding, reached by phone, says she accommodates requests from filmmakers like McNamara pretty often. She welcomed the east coaster’s physical video into the store. It’s now a conversation piece, resting on the coffee table in the store’s “living room” area next to the vintage couch and TV. (Blockbuster no longer rents VHS tapes, instead showcasing them as relics from the analog era.)

Harding said she was a little taken aback that McNamara would personally travel from New York for the occasion, but she makes a point of spreading her love of physical media, as she does when Blockbuster plays host to school field trippers and sojourners, alike.

While in Bend, McNamara jogged 14 miles along the Deschutes River Trail, wearing Blockbuster-themed socks and, you guessed it, a new pair of Pit Vipers.

McNamara counts his trip to Bend a success.

“Sandi is a real gem. Let’s give her the Medal of Freedom,” he said. “She’s doing more for Americana than most.”

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Peter is a feature & investigative reporter supported by the Lay It Out Foundation. His work regularly appears in the Source. Peter's writing has appeared in Vice, Thrasher and The New York Times....

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