Who Played Willie Oleson on ‘Little House on the Prairie’? Meet Jonathan Gilbert and See Where He Is Now

Hold on to your bonnets! With Netflix’s remake of the beloved ’70s family drama Little House on the Prairie on its way, Closer rounded up everything fans need to know about the OG Willie Oleson, played by actor Jonathan Gilbert.

Who Is Willie Oleson on ‘Little House on the Prairie?

The younger brother of spoiled, scheming Nellie Oleson (Alison Arngrim), Willie is one of Walnut Grove’s most mischievous schoolboys. A poster child for pint-sized trouble, Willie’s the kid who tosses spitballs in Miss Beadle’s classroom, plays pranks with glee and regularly torments the well-behaved kids (especially Laura Ingalls, played by his real-life sister, Melissa Gilbert). Although his overprotective parents, Nels and Harriet Oleson (Richard Bull and Katherine MacGregor), rarely punish him, Willie is often sent to stand in the corner at school.

As the years go by, Willie grows out of his childish ways and becomes a responsible young man. He falls for his sweet and loving classmate, Rachel Brown (Sherri Stoner), and announces his plan to marry her. Snooty Harriet, however, doesn’t approve. She thinks her son could do better. But Willie’s not having any of Harriet’s nonsense. He and Rachel tie the knot and go on to manage the family hotel-restaurant named after his sister, Nellie.

Who Plays Willie Oleson on ‘Little House on the Prairie’?

Behind the role of Willie was Jonathan, a young actor with a unique connection to the Little House world. Born on April 28, 1967, Jonathan was adopted by actors Barbara Cowan and Paul Gilbert. His adoptive sister, Melissa, starred as Laura Ingalls, the heart of the classic series. Jonathan was just 7 years old when he joined Little House on the Prairie, and he remained with the show for its entire run — from 1974 to 1983. “I remember auditioning for Michael Landon (who played Charles Ingalls), and he just laughed and laughed, and as a kid I didn’t know what the hell he was laughing about,” Jonathan, 58, recalled to Closer. “He was magic. One of the greatest actor-directors ever.”

Where Is ‘Little House on the Prairie’ Actor Jonathan Gilbert Now?

Despite growing up on screen, Jonathan never sought out the spotlight in the years that followed. After the series ended, he gradually withdrew from acting, appearing in a couple of Little House TV movies before he decided to leave showbiz altogether. Unlike Melissa, Jonathan chose a completely different life. He moved to New York City, earned an MBA and built a successful career in finance.

Today, he works as a stockbroker and lives far from the hustle and bustle of Hollywood. Unlike many child actors of his era, he chose privacy and distance over a continued career in entertainment. Although he remains mostly out of the public eye, last year he reunited with his former Little House cast members for the show’s 50th anniversary. The fact that it’s still such a hit today is no surprise to Jonathan. As he told Closer, “It’s the holistic, familial relationships that are not part of our culture anymore that make Little House timeless.”