The world lost one of the most innovative minds in the history of comedy Thursday when humorist Garry Shandling died suddenly at the age of 66. 

A comedic genius who never compromised on his slightly dark, deadpan sensibility, Shandling's brand of humor was so unique that it led him to reject some of the most coveted opportunities in entertainment purely because of their conventional nature. "I would not do a show where you just sit and talk to somebody," Shandling said in 1993 after turning down an offer to take over David Letterman's show, Late Night. The position eventually went to a then-unknown comic named Conan O'Brien.

Here are three examples of how Shandling reinvented comedy time and again with innovative ideas that audiences had never seen before.

1. Disrupting the situation comedy.

Shandling's first TV series, Showtime's It's Garry Shandling's Show, was a sitcom that Shandling and his fellow actors frequently turned on its side by speaking directly to the audience and openly discussing the fact that they were performing in front of cameras. In an episode where Shandling's nephew Grant accused him of trying to steal his 12-year-old girlfriend Kim, Grant says, "Every week you try to pick up all the actresses on the show, but to stoop to this?" Even the show's theme song poked fun at the format, including lyrics like, "Garry called me up and asked if I would write his theme song. I'm almost halfway finished. How do you like it so far?"

2. Mixing real life with make believe.

In Shandling's second show, an HBO comedy series called The Larry Sanders Show, he played a fictional late night talk show host who interviewed celebrities playing exaggerated versions of themselves. The show straddled the line between reality and scripted comedy by making it hard to tell when celebrities were acting and when they were just playing themselves. In a scene that took place during the fake talk show's commercial break, Shandling's character urges Robin Williams not to appear on competing shows hosted by Arsenio Hall and Jay Leno. "I've got to," Williams says. "It's a business, get used to it." The concept of having real celebrities play caricatures of themselves was later copied on show's like NBC's 30 Rock and HBO's Curb Your Enthusiasm. 

3. Interrupting live TV.

Even when Shandling appeared on other people's shows, like HBO's live show Real Time With Bill Baher, all bets were off when it came to what he might do to be funny in an unorthodox way. In 2007, after Maher interviewed neurosurgeon Sanjay Gupta remotely via video conference, he turned to Shandling and asked if he was aware of the threat of honeybees going extinct. "I just didn't know we could do a satellite feed," Shandling said. "I could be in Vegas right now. I'll probably go before the end of the show."

Shandling's innovative approach to humor even shined through when he was practicing the most conventional type of comedy: stand-up. While hosting the Emmys in 2004, he pointed to Donald Trump in the audience. "Nice to see a man who's paid his dues, worked hard," he said. "We all know what it feels like to have to build 80-story condos and gambling casinos just to get our foot in the door in show business."