Q&A with Bill Oakley
Bill Oakley has been a professional screenwriter for over 30 years. Most famously, he wrote for The Simpsons with his writing partner Josh Weinstein. The two were set writers for seven years, and eventually showrunners for its seventh and eighth seasons, largely considered to be some of the series’ best years. The duo went on to write for Futurama, then created their own shows with, as Oakley puts it, “various levels of success over the next few years.” Oakley currently resides in Sunnyside and runs a wildly popular social media presence that revolves around niche fast food items. He hosts a tour of his sleeper hit series Mission Hill, screening remastered versions of the show’s single season at theaters across the country.
How long have you lived in the neighborhood, and what brought you to Portland?
Bill: I’ve lived here for more than 14 years, and I’ve been in this house the whole time. We have friends who live near the Belmont Library. They had moved in the ‘90s and were evangelizing Portland. We visited and agreed it was a great place to raise a family, and it wasn’t so far from L.A. that I couldn’t travel down there. It took almost as long to fly to L.A. as it did to drive to Burbank from Santa Monica, and that became less and less necessary as time went on. I began doing more and more work online as we got closer to the pandemic, and now the work doesn’t even ask you to come to L.A. anymore. The last two shows I worked on didn’t even have office space; it was all online.
Do you rent or own this house?
Bill: We’ve been renting it for over 14 years. I owned houses for 16 years in L.A. and I didn’t want to ever own a house again after that.
What do you love about Sunnyside?
Bill: When we were first considering moving to Portland we went on a driving tour of sorts through every neighborhood. It was the perfect neighborhood! You could walk everywhere. There are restaurants and stores and interesting things going on. It was the polar opposite from L.A., where, from our house, it was a mile walk
to get anywhere – with no sidewalks. We found a house near Hawthorne, and when it came up for rent we were like, “That’s the house.”
There have been about four incarnations of this neighborhood since we moved here…. There’s still plenty of interesting things to walk to. I love Sewallcrest Park. I love that I can walk down to Division. I love being able to walk up and down Hawthorne, which I do frequently. I can walk to grocery stores in less than ten minutes. I love going to Zach’s Shack. Quarterworld is terrific. I love Powell’s Books and the Bagdad Theater. There are good food carts, and the best cart pod in easy reach of us now is the Hinterlands on 50th. To sum it up: there’s a great mixture of interesting things and places to eat, all within a short walk. As far as any big American city, it’s relatively safe.
What is one thing you would change about Sunnyside, if you could?
Bill: I would add a few more useful things, like the Postal Annex on Hawthorne I go to literally every day. Some of the useful things that used to be here… a place to pick up a quick sandwich to go, or Noah’s Bagels. I’m not saying national chains—one thing I miss was the Dollar Scholar. I could send the kids over with a few dollars to buy balloons or sodas. It encapsulated the quirkiness of the neighborhood. Missing Link was another place; I would really love to have another store like that. If I could push a button and have one thing, it would be to have Bodega PDX open a spot on Hawthorne. I love the sandwiches and you can pick up whatever you need.
Final question: Are you more of a cat person or a dog person?
Bill: I have four cats. It doesn’t mean I don’t love dogs, I just don’t want to have to walk a dog. The cats are great pets, but while they don’t have quite the same enthusiasm for people as dogs do, they’re fun and have unique personalities. And, you don’t have to walk them. The cats are named Piper Po, Mochi, Scooter, and Kitty Bennet. These are not all my cats, but they all live here, and they’re each bonded to their particular human. I inherited Kitty Bennett, who is now attached to me.
Follow Bill Oakley on Instagram & Twitter (@thatbilloakley) or Facebook to see his reels on the Heinz Remix Machine, Lay’s Mayonnaise flavored chips, and updates on Mission Hill screenings.