It's not a show, or at least it wasn't a show last I looked, but John Grisham's The Rainmaker was about insurance. It was a book first, then it was a movie. I'm not sure because a few books that have been adapted into movies were later adapted into shows. The Lincoln Lawyer was one; I seem to remember a few others.
The story (/plot) is, a guy dies of cancer because the drug that could have saved him wasn't approved by his insurance company. He'd paid his premiums for decades, but they denied him and he died, so his family sues. It's John Grisham, so you can kinda guess the ending, and maybe the twist, but it was still super satisfying.
There's a scene in Fight Club that tackles insurance in a similar way. It's a line people often quote, about how when the car companies find out there's a flaw, they run an equation on how much they'd have to pay out in settlements vs the cost of a recall and they go with whichever is cheaper. Similar stuff.