Alumnus Q&A: Phil Olson ’79, comedy writer and playwright

by Emma Guo | 10/18/16 12:00am

Phil Olson ’79’s award-winning career in comedy began unexpectedly. After graduating from Dartmouth with a degree in mathematics, Olson received an MBA from the University of Chicago and initially pursued a career in real estate. It was only then that he discovered his love for comedy writing. Olson went on to write and perform with The Groundlings, an improvisational and sketch comedy theater whose alumni include Maya Rudolph and Kristen Wiig. Olson has written 13 original screenplays and 15 published plays with over 350 productions worldwide, nine of which have been published by Samuel French. His next play, “A Nice Family Christmas,” will open in seven cities this year.

At Dartmouth, you played football, ran track and majored in math. What brought on the transition to playwriting and screenwriting?

PO: After business school, I was in commercial real estate development in Florida when one of my tenants asked me if I would act in one of their industrial films. I had never acted before, but I figured it would be a good time, and it would be on the weekend. When I showed up on set, it turned out that they never had any written scripts, so I had to improvise the scenes. They kept asking me back week after week since I could write the scenes on the fly. I really enjoyed doing that, so from there I got into a sketch comedy group in Florida, performed in a bunch of plays and eventually moved to Los Angeles to write screenplays. Now I write and produce plays full-time, and my business experience has really helped in terms of advertisement, actor hiring and public relations.

What would you say is the most difficult aspect of writing a script or putting on a play?

PO: Last year, I was producing one of my “Don’t Hug Me” musicals in Minnesota, and a week before we opened, one of my actors ­— my general manager, Ross — had a heart attack, died, was brought back to life and went into a coma for eight days. Then, two of the other actors dropped out because it was such a traumatic experience for them. So I lost three of my actors six days before the show opened. But of course, the show must go on. I ended up having to recast three of five actors with six days to go and four rehearsals. And we did it — we pulled it off for Ross.

As for writing, they say you never finish a play; you just abandon it. Writing is all about rewriting — you don’t come out with a finished product (at least I don’t). The hardest part about writing is the first draft, and the second hardest part is the second draft. When I finish the first draft of a play, I do a reading of it in front of an audience. After the reading, I’ll sit on the stage and ask the audience questions: What worked, what didn’t? Usually the first and second drafts are really painful for me because I miss so many things that make a good story — conflict, high stakes, character wants and needs. Even though I’m aware of all the elements of a good story, I don’t always start there, so I do several readings of my plays, taking shots from audiences all around the country, editing along the way.

I noticed that your “Don’t Hug Me” plays are set in Minnesota, your home state. Would you say that your upbringing there in some way inspired the setting or events of the play?

PO: Yes, that’s exactly right. They say to write what you know, and I grew up in an emotionally reserved Scandinavian household in Minnesota. My father would tell us that he was the Norwegian who loved his wife so much that he almost told her. The closest we ever came to hugging was that awkward shoulder hug. Eight of my plays and musicals are about my Scandinavian upbringing, and five actually have “Don’t Hug Me” in the title. My play “A Nice Family Gathering” is about a man who dies and comes back to his family’s Thanksgiving dinner with a mission: to tell his wife of 35 years that he loves her. It’s a story that I wrote after my father passed away. I also have a play, “Mom’s Gift,” in which I combine my Minnesota upbringing with my Dartmouth background. It’s set in Minnesota, but the main protagonist is a Dartmouth graduate. She majored in math, like I did, then got an engineering degree from MIT, so she’s a lot smarter than I am. I wrote “Mom’s Gift” for my mother, after she passed away, and I would love to have Dartmouth put on a production one day.

Can you tell me a bit about your experience in The Groundlings?

PO: That was a great experience. I went through every level of the program and had the good fortune to write and perform with Maya Rudolph and a lot of really talented comedy actors and writers. That’s where I learned how to create characters and write three-minute short stories. The Groundlings actually produced my play “A Nice Family Gathering,” which played in 120 cities around the world. I would highly recommend going into The Groundlings for any Dartmouth graduate that moves to Los Angeles to pursue acting and comedy.

How would you say your Dartmouth experience has shaped who you have become as a person?

PO: Well, I grew up in a very vanilla environment — wholesome, Midwestern. There wasn’t a lot of diversity. Dartmouth was a real eye-opener for me in that there were so many people from different backgrounds with different interests and opinions. And I really had to adapt quickly. I would say that Dartmouth really helped me learn the skills that you need to be able to work with people from all types of backgrounds. Also, being involved in football, track, fraternity life and Casque & Gauntlet allowed me to meet a lot of very interesting and funny people, which has really shaped my comedy writing.