ImprovBoston Goes Back to the '80s with Hit Comedy Show OREGON FAIL

ImprovBoston Goes Back to the '80s with Hit Comedy Show OREGON FAIL

ImprovBoston brings those who grew up in the 80s back to a simpler time when they trekked westward on their Apple II GSs - hunting, crossing rivers, and avoiding the dreaded dysentery outbreak. Based on the popular 80s video game Oregon Trail, ImprovBoston's hit comedy show Oregon Fail: You Have Died of Comedy combines thrilling adventure and whimsy in a completely improvised show set within the world of the game.

Improvisers encounter the same dangers as their ten-year old selves: roving buffalo, local shopkeepers, and cholera epidemics. In between those dangers, wagon crew members hunt an ever-dwindling buffalo population and talk about the vast riches they will one day have should they ever make it to Oregon.

How it all began

"The idea for this show came about when I talked with another comedian about how ridiculous the 'world' of Oregon Trail is. If you're that frustrated playing the game, how do those 8-bit people on the wagon feel? We only ever see prompts that people have died of disease or that they need to cross a river. Who are these people? What do they talk about? What's going on in that wagon and those forts you stop at?," explains Show Producer David Thomas. "I ran these thoughts by local improv legend John Serpico, and he turned my idea into a marvelous show that allows for improvisers to create rich, genuine, and hilarious characters who explore this insane pioneer world. Every member of the cast has made this show into something I'm proud of. We sold out every show in 2016."

Director John Serpico agrees the cast makes the show. "What I love about Oregon Fail is the cast gives the audience the world of the game, with hunting, trading, snake bites, and Chimney Rock," Serpico says. "But the audience also sees characters deal with the world in real and compelling ways. They're obsessed with starting a new life in Oregon. They might run from something or have some great dream that can only be fulfilled at the end of a harrowing journey. So we have both the fun of the game and the character drama of a family pushed to the edge."

A connection back to the game

This throw-back show didn't only grab the attention of sellout crowds in 2016. The son of Oregon Trail's co-creator Don Rawitsch also caught wind of the comedy show. Jeff Rawitsch trekked to Cambridge last January to thank the ImprovBoston cast for honoring his father's creative legacy and to chat with them about the game that looms large in the collective millennial memory.

Jeff's favorite parts of the show: the 8-bit folk song transitions between scenes, the number of times cast members mentioned "grueling pace" and "rations," and the "floating hat" imagery cast members used each time a pioneer died along the river.

Oregon Fail: You Have Died of Comedy is a 90-minute show that runs every Friday at 10PM through September 1. Tickets are available at

For over 30 years, ImprovBoston has been New England's leading theater and school dedicated to the art of comedy in all its forms. Voted "Best of Boston" by The Phoenix, The Improper Bostonian, and The Weekly Dig, ImprovBoston performers, teachers and students have included film stars, Emmy Award-winning comedians, and acclaimed producers, directors, musicians and writers. ImprovBoston alumni are featured on Conan, Late Night with Stephen Colbert, The Daily Show, America's Got Talent, Funniest Wins, Playboy, Last Comic Standing and John Oliver's Last Week Tonight, to name a few. In 2014, the Independent Reviewers of New England honored ImprovBoston with an award recognizing its longstanding contributions to the Boston theater community. As a nonprofit arts organization, ImprovBoston serves the community through laughter with youth outreach programs, workshops for businesses, scholarships, a national touring company and, of course, performances at its theater complex in Central Square, Cambridge.

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