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So it only makes sense that the 77-year-old funny man now has his own talk show.
Premiering on Friday, "Almost Legal with Tommy Chong" is touted as a mixture of Marc Maron's "WTF" podcast and the traditional late night talk show style of celebrity guests and occasional skits.
But Chong said what it will mainly have is his views on pretty much everything.
"You can get a lot on TV nowadays," Chong told Business Insider. "But what you can't get is my personal take on things, and I think there's an interest in what I have to say."
One sample of what you might get on the show is Chong's decades-worth of run-ins with famous (and infamous) people.
Like how he was a big inspiration behind the creation of the book "The Wolf of Wall Street."
Chong roomed with the book's author, Jordan Belfort, when Chong was serving nine months at Taft Correctional Institute in California for selling drug paraphernalia. (Belfort had just started a 22-month stint for fraud and money laundering).
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Chong said one day Belfort noticed what he was doing and told Chong that he also was interested in writing a book of his time as a stockbroker and trader. One day, Belfort was in their cell and had a page and a half written out. He passed it to Chong to get his opinion.
"I'm usually not a guy that critiques anything, but I just had an instinct that Jordan is a genius and with geniuses you push them harder than most," said Chong. "I noticed that he was copying Tom Wolfe and I pointed that out to him, I think he was a little pissed off at me that I critiqued him so hard."
But Chong gave the soon-to-be-author a piece of advice that would turn the book into a page-turner that would later grab the attention of Martin Scorsese to adapt it into a movie starring Leonardo DiCaprio as Belfort.
"I pointed out that people are only interested in the 'most of,' that's exactly the phrase I used," he explained. "I described it to him as, 'If you go downtown to go shopping and you go home, that's not exciting. But if you go downtown and there's a car accident and you save someone's life and it turns out to be someone famous, that's a 'most of.' So you have to tell the 'most of' and they have to be true.' He listened to what I said because he had the best "most of" stories I've ever heard in my life."Belfort finished the book after he got out of prison, and though he only made a reported $330,000 on the book deal, the adaptation by Scorsese scored him more exposure the book ever would, as the film was nominated for five Academy Awards in 2014.
If Chong plans to dish out stories like this on his show, he's got something good in the making.
"Almost Legal with Tommy Chong" is available on FilmOn.com or FOTV on the Dish Network. New episodes air every Friday at 5PM PST/8 EST.