October 1, 2024.

TEN YEARS OF SPOOKTOBER STORIES: A CONVERSATION WITH JON PHILLIPS

When I meet Jon Phillips on the patio of his Malibu home, he’s painting a pointillist landscape from memory. He stands back, peering, trying to get the clouds right, and begins to dab again with the brush. He’s healthy, lithe, his full head of black hair well coiffed and shot through with a little respectable grey, marking his thirty-five years. He’s clean shaven, and his lean, handsome face is tan and unlined by worry or self-doubt.

It’s a far cry from how most of us know him, playing a distorted version of himself on the hit “Spooktober Stories,” which is beginning its tenth year this October 1st.

The “Jon Phillips” in that show never left Phillips’ real-life university town of Milwaukee, is an underachieving slob, a layabout ne’er-do-well who fancies himself an undiscovered creative genius (despite never actually creating anything other than the titular ‘Spooktober Stories,’ which he inexplicably posts on Facebook just one month a year), can’t hold down a steady job, sabotages his relationships, and struggles to accomplish even the most basic tasks. ‘A schlub without much of a future,’ as the Spooktober Stories series bible succinctly describes him.

The real Jon Phillips hops off the patio with an athlete's grace to walk and talk with me through his elaborate garden, which he takes pride in growing and maintaining himself. I compliment him at maintaining such peak physical prowess, despite being best known for playing a role that’s quite the opposite.

“I always feel lighter when I’m not carrying him around,” he says, patting his belly and laughing. (Phillips is a streamlined 150 pounds, but to portray his rather more sedentary alter-ego, he has to go through a grueling makeup process every morning, concealing well-defined muscles, adding jowls, the beard, deep eye bags, putting in crooked, yellow teeth, and then strapping on a *sixty-five pound* prosthetic belly, sometimes heavier, depending on how hard “Jon” has been hitting the McDonalds and the McKenna that season.)

Phillips has a complicated relationship with the character. “He’s a comic character, obviously, and we’re supposed to laugh at his bumbling personal failures and rapidly disintegrating mental capacities, but honestly, sometimes I feel sorry for him. This could easily have been me, if I never did anything with my life, if I just gave up. But then sometimes I get really angry with him. I just want to reach through to him and scream in his face, ‘what are you doing, what are you doing, what are you doing! Why aren’t you doing anything! Please, God, please, you’ve wasted your whole f---ing life!’”

He stares off into the distance, ruminating on what he’s said, but soon enough the shadow passes from his face, and he turns to me with a boyish, charming, full-toothed smile. There’s always a twinkle in the real Jon Phillips’ eye, a little mischievous glint, and I joke that getting rid of that to achieve the famous dull-eyed glaze for “Jon Phillips” the character must take an extra hour in the makeup chair.

Jon laughs. “No joke, I’ve gotten in so much trouble for that. I’m always supposed to be avoiding certain lights and turning my head just so, and… Jessie [Fievan, series director of all ten years of Spooktober Stories] will shout ‘Less joy! Less joy! You’re supposed to hate yourself, get rid of that g-d-damned zeal for life, Phillips!’ It’s a struggle. It’s a struggle.”

Before I leave, I ask him, should we start gearing up for ten more years of Spooktober Stories?

“I think if we pretended with the direction his life is going that Jon was going to live another ten more years, CinemaSins would send a trained hit squad to ding us to death,” he chides, referencing the popular YouTube series that ‘dings’ when there are factual inaccuracies in movies and television. “No, no, we won’t hang it up prematurely, but I think when a natural ending presents itself, we’ll take it.”

“Besides,” he muses, walking me to the door. “It’s hard enough to watch a relatively young miserable bastard failure not doing anything. If I had to watch a program about a middle-aged miserable bastard failure not doing anything I think I’d shoot myself in my own f---ing head.”

WELCOME TO SPOOKTOBER STORIES: SEASON 10.