NAME: Theodore “Theo” Jackson
GENDER & PRONOUNS: Cis Man / He/him
AGE & DATE OF BIRTH: 34 years old / May 1st
HOMETOWN: Westerly, RI
TIME IN WESTERLY: Returned 1 year
RESIDENCE: Watch Hill
OCCUPATION: Musician, producer & owner of Sound Wave
I’LL BE YOURS FOR THE WEEKEND —— tis the damn season.
Theodore Jackson really didn’t think he was making it out of Westerly. His family was generations of stone fabricators that worked with the granite that came from the town that spent their free time wearing out the cushion of a stool at the local bar. Everyone on his father’s side did it, so there was the expectation that Theo would be following in those footsteps. But things took a drastic turn when his mother left; frustrated by her husband's inattentive behavior, she packed herself a bag and left after dropping Theo off at kindergarten. It left an angry Willam Jackson to balance a full time job and his son on his own. All in all, the cards weren’t in Theo’s favor. But growing up, it was all he could think about. He wanted to disappear from this town that had every decision made for him before he was even born. Theo spent countless nights, laying on his back in the sand next to his best friend Willa, describing what he wanted to do with his life away from this town. Because maybe, just maybe, if he kept saying it, it’ll come true.
When he was ten years old, after his father forgot to come home after a full 48 hours, and Theo had to call his aunt to ask for help turning on the oven, he was placed in the care of his aunt. She was the one that put him in the after school music program, where he picked up a guitar for the first time. After that, it was all over. Theo’s time was either spent out on the beach, surfing with his closest friends, or he was sitting there with a guitar in hand, showing off the songs he learned that week and eventually, the ones he wrote. As middle school turned to high school, girls were starting to notice him. Wondering if the songs written in the margins of his math homework were about them - when they were the farthest from his mind. At a glance, Theo and Willa’s friendship was what someone would describe as extremely close. They had their small friend group, but you really didn’t see one without the other a lot of the time. But if you looked closer, you’d see Theo’s eyes lingering a little bit longer on the girl with the untameable curls. And maybe their hands brushed as they walked, and school dances always had a moment where the two of them swayed to the music together in their own little world, even if they brought other people.
Willa was the reason he might want to stay in the town that he loved at arms length, but as senior year of high school came around, and a performance at the town holiday festival, where a music producer visiting family heard him sing an original song, his way out was handed to him. A record deal. In Los Angeles. Everything he could’ve wanted and more. But he had to leave after graduation. Which meant saying goodbye to his family and whatever there was between him and his best friend. Saying goodbye was more difficult than he thought, but with a promise of coming back to visit, Theo was off. He wasn’t an instant hit in any sense of the word. But Theo workshopped and sold songs he wrote for other artists while still working hard on his own. And a few years later, with the dawn of YouTube, Theo found his break.
A video he recorded with his friends on a whim, a five part harmony of Last Christmas around a fire, went on YouTube as he was getting on a plane home for the holidays. When he landed and went to show his aunt the video, he saw emails upon emails and a six digit number next to the word ‘views’. The producers he worked with behind the scenes now wanted him in a booth, and did he have demos to send? He did. And that year’s Christmas gift to himself came in the form of a record deal. Deciding that the home he was raised in, with the woman who dropped everything to keep him safe - who legally adopted him later in life - was good luck. So he found himself returning every year for the holidays. Never missing a single Thanksgiving or Christmas. Some years, when tours weren’t happening and albums were still in the writing stage, he’d stay from Thanksgiving all the way through New Years Day. He loved his family, he owed a lot to his family. And the only way he knew how to say thank you came to him a Christmas ten years after the initial record deal. He bought his family a home on the beach in Misquamicut.
Though, the house wasn’t the only surprise through the years. Every time he returned home, the first person he reconnected with was Willa. His closest and oldest friend, someone who he wanted in his life forever. But they weren’t really meeting in a just friends capacity. It started when they were 20, at a holiday party with most of the town. They found themselves updating each other on their lives and Theo acted on a thought that was plaguing the back of his mind since he was a kid. He finally kissed Willa. That kiss led to falling into bed together, which led to awkward conversations when it was time for Theo to pack up and head back to the west coast. But every year, they repeated the cycle. No matter who they dated throughout the year, it was always the same. It wasn’t enough for Theo, who, as the years went on realized that maybe the reason his relationships weren’t sticking wasn’t because of the industry, as so many people in his life and in the tabloids liked to point out, but because they weren’t with the right person.
But the years went on and things stayed the same. And as Theo lived his dream of topping charts and touring the world and being away from the town that raised him, he started to realize that maybe his need to leave was a childish dream. He was finding it harder and harder to leave each time he returned. And the city was getting too loud, too hot. He was getting older and was ready to settle down. And that was definitely not something he wanted to do in LA. Theo had no idea what he was going to do, until he came home for his grandmother’s birthday and saw an open storefront downtown. It was a rash decision to purchase it, but his last album was doing well, and he had already thrown around the idea of moving to a purely production and songwriting role after his next album, and a house had opened up on the water on Watch Hill. Things were lining up perfectly.
Everything led back to Theo’s hometown, and he’s wondering where that town will take him next.
Portrayed by GARRETT HEDLUND, written by LINDSEY.
