Tom Skilling Improvises His Way Through Cameo On ‘The Bear’

Editor’s note: The following article reveals some details about the final season of “The Bear.”

CHICAGO — The final season of “The Bear” skipped the show’s usual culinary tour of Chicago for a tightly focused bottle season set almost entirely in the walls of the titular restaurant — but Chicagoans still got a taste of home with an extended cameo from a television fixture.

The show’s penultimate episode, “Caramel,” which featured the restaurant’s stressful make-or-break service during a torrential rainstorm, played host to the man Chicagoans trusted with the weather for nearly 50 years: meteorologist Tom Skilling. 

Skilling, who plays himself in the episode, reported on the weather as WGN-TV’s chief meteorologist from 1978 until his retirement in 2024. He also wrote the daily weather column, “Ask Tom,” for the Tribune until 2022. He still occasionally makes appearances on air, as when tornadoes and storms tore through Illinois this June.

In “Caramel,” Skilling’s reputation precedes him, as the characters wine and dine him and pry him for info about the rainfall while he enjoys dishes brought out by restaurant staff. 

In an interview with Block Club, Skilling called the critically acclaimed show “such a feather in our cap” for Chicago. He said he was approached to do a cameo while he was in Hawaii, and producers offered to pay the cost of his flights to Chicago for filming and then back to Hawaii.

“I would have done it even without the offer,” Skilling said.

A fan of “The Bear” since its premiere in 2022, Skilling said he admires creator Christopher Storer and how the show has become a “source of discussion” in the city.

For filming at the soundstages at Cinespace, 1501 S. Rockwell St., Skilling brought two options for a suit and let Storer and the cast and crew help him through his scenes. 

As it turned out, there was no script: Skilling’s appearance was completely improvised. The actors playing restaurant staff brought out different dishes during the scene, and Skilling and others sitting at the table with him were simply told to react as they would in a real restaurant. 

One of those at the table was a character named Mr. Dearborn, played by actor Peter Grosz. That was somewhat ironic — Grosz played Nicolas Cage’s archery instructor in the 2005 film “The Weather Man,” about a Chicago-based meteorologist. Skilling was a consultant on the film.

“We were laughing that we had that mutual experience,” Skilling said.

What marveled Skilling most about the set was that culinary consultant Courtney Storer — Christopher Storer’s sister — built a full, working kitchen in which the food was prepared. For Skilling, it was just as pitch-perfect as any Michelin-star restaurant in Chicago.

“The meals are served in such a beautiful way, you almost hate eating them,” he said.

One of the episode’s major turning points involves Corey Hendrix’s sommelier, “Sweeps,” serving a bottle of “the ’97” to Grosz’s character (whom the crew presumed was the “star man” evaluating them for the Michelin Star guide that night). That meant Skilling had to also act like he was a wine connoisseur. In reality, though, Skilling is “not an expert on wine at all” and followed Grosz’s lead in swirling and swishing around the wine — which was non-alcoholic, he said.

“They would come up and lay some lines on me, and I’d think, ‘God, how am I supposed to respond to this?’” Skilling said. But he rolled with the punches and reacted as he would in real life, saying whatever came to him in the moment.

“I think they wanted that natural flavor,” he said.

This was doubly true for the climactic moment where actor Matty Matheson’s Neil Fak approaches their table to present a dish, and he leads Skilling and Grosz into a conversation about his tattoos.

“Matty was a delight,” Skilling said.

The trio filmed three or four versions of the scene so the creators had options to choose from. It was a highlight of Skilling’s time on set.

“[Matheson] has one of those delightful faces that, the minute you see it, you begin to smile,” Skilling said.

While Skilling might not be enjoying any more meals at The Bear, he remains enamored of so many of Chicago’s fine dining establishments. His favorite — real — restaurants include RPM Seafood Chicago, 317 N. Clark St.; Shaw’s Crab House, 21 E. Hubbard St.; and Michael Jordan’s Steak House, 505 N. Michigan Ave.

“One of the amazing things about living in Chicago is the range of choices you have,” Skilling said. “We have some amazing eateries around here, and it’s fun to go out there and really try them.”

At the end of the day, Skilling hopes “The Bear” will help show the world the wonders Chicago has to offer.

“Do you know this city has been called a war zone?” Skilling said. “It’s not. It’s a marvelous city. It’s friendly, it’s warm. And hats off to Christopher Storer to give people a sample of how we live here and how our restaurants operate.

“I’m just proud to death.”

All five seasons of “The Bear” are now available to watch on Hulu and Disney+.