‘Wheel of Fortune’: Drama Teacher Can’t Stop Laughing After Winning $45,000 Cadillac

A Wheel of Fortune contestant was so surprised that he won a brand new Cadillac on Tuesday’s (October 28) “Halloween Week” episode that all he could do was laugh and laugh and laugh.

The contestant in question was Stephen James, a drama teacher from Burbank, California, who was up against self-described “Halloween Queen” Lynn Silverman from Jensen Beach, Florida, and horror movie buff Sean O’Connor from Colleyville, Texas, whose sister Krystal appeared on the show in April 2015 and won two trips and a car.

James started the episode well, solving the first two puzzles, but he landed on Bankrupt twice early on. Fortunately, Silverman and O’Connor continued to make mistakes, allowing James to take the lead. In the Express Round, James capitalized on O’Connor’s error to continue guessing letters and solved for a trip to Nova Scotia worth $8,103.

After solving two more puzzles in the Triple Toss-Up, James essentially secured his win, even with O’Connor snatching $6,600 in the final Speed-Up Puzzle. In the end, James won the episode with $17,103 and a trip to Nova Scotia.

Heading into the Bonus Round, James selected the “What Are You Doing?” category, along with the letters “P, H, G, and I,” giving him a three-word puzzle that read:” _ _ _ I N G / _ / P I E.”

It didn’t take long for James to figure it out, screaming out “Baking a Pie” twice, just to make sure he was heard. Things only got better from there when host Ryan Seacrest opened the prize envelope to reveal James had won a 2026 Cadillac CT4 Premium Luxury worth $45,070.

“Woohoo!” James screamed. He continued to yell “Oh my God” in between wild fits of laughter. The giggling carried on as he jumped into the driver’s seat of his flashy new car.

Wheel of Fortune YouTube

“Stephen is just so lovable. I think we were all rooting for him,” wrote one Reddit user.

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“He was my drama teacher in middle school and literally everyone loved him. Couldn’t deserve it more,” said another.

“I met Stephen when I taped my episode. He was an alternate and didn’t tape that day. What a genuinely nice guy!” another added.

Another wrote, “Congratulations to our new car winner. Job well done Steve.”

In the end, James will be laughing all the way to the bank, with an overall total of $62,173 cash and prizes.

Did you figure out this Bonus Puzzle? What did you think of Tuesday’s episode? Let us know your thoughts in the comments section below.