But, it was another brush with fame that very nearly changed Che's life, and the trajectory of his career. One day, while Che's table of shirts was set up in Manhattan's SoHo neighborhood, his designs caught the eye of Richard Hilfiger (the son of fashion icon Tommy Hilfiger), who briefly chatted with Che. A few weeks later, Richard returned with his father in tow, at which point Tommy Hilfiger bought a few of Che's shirts. The elder Hilfiger even ended up offering Che some freelance work designing logos for his clothing company.
"Tommy Hilfiger comes by and he's like 'Oh man, I love your stuff. Come on down to the office and I'll give you a job, or something.' And, I'm like, 'Alright!'" Che revealed on NBC's "The Tonight Show Starring Jimmy Fallon" in 2017.
Hilfiger even invited Che to his company's Manhattan office to praise him in front of his employees and to give Che some money upfront.
"He introduces me to everybody in the office individually, and he's like, 'This is Michael Che. One of these days he's going to be a great artist.' And, I was like, 'What is happening?!'" Che told Fallon.
Hilfiger gave Che $1,000 in cash, with the agreement that Che would create a series of designs. "He said, 'You know why I'm giving this to you? Because somebody gave me a chance, and I'm giving you a chance.'"
The moment could have been the inspiring origin story of a future fashion mogul, but unfortunately, Che says he never made good on his agreement with Hilfiger. Che never made any designs and he never returned to Hilfiger's office. Looking back, he says he was paralyzed by anxiety and the fear that he wouldn't be able to create anything worthy of Hilfiger's praise.
"Now, in hindsight, I know what it was. I was scared," Che told Splitsider. "But then, I just didn't understand. Nothing looked right, I just couldn't. They set me up with like a whole work area, they gave me a computer and a desk and all that shit, and I could do whatever I wanted. I could come and go as I please, I had no boss. I was working for Tommy. And I just couldn't do it."
Che told Hilfiger he worked better from home, so he stopped coming into the office. But, as the weeks passed, he still never turned in any designs. "And a week turned to two weeks, because I was too embarrassed … I was honestly just terrified," Che says.
The experience taught him a lot, Che says. "I had an opportunity that I thought was change my life. And I f------ blew it completely, just from being scared," he told Vulture. "So now, when I do comedy, I ain't scared of s---. I'm like, just take advantage of every opportunity I get, because I don't know. How you gonna get lucky twice?"
(A corporate spokesperson at Tommy Hilfiger did not immediately respond to CNBC's request for comment.)
After the embarrassing end to his freelance gig with Tommy Hilfiger, Che was afraid to go back to selling his shirts on the street — fearful that he'd run into Hilfiger or his son. With his T-shirt business struggling, Che says he became depressed and stopped painting altogether.
"At that point, I couldn't do it anymore. I was tired. And I was depressed," he told Vulture.
Che decided that he needed a totally new career, and that's how he ended up starting out in comedy. Che had loved comedy since he "was in diapers," he told Vulture, which is one reason why iconic comedian Richard Pryor was one of his painting subjects.
In October 2009, at the age of 26, Che first started performing stand-up comedy at open-mics around New York City. While it takes many comedians years to experience any success in stand-up — and countless others never do — Che's comedy career took off amazingly quickly, helped by his intense dedication to getting better onstage and working on his material.
"I went onstage every day, maybe two to three times a day, just open mics, open mics, open mics. Maybe four times a day. Maybe five times a day," he told the Village Voice.
Soon, Che was performing at iconic New York comedy clubs like Caroline's and the Comedy Cellar. In 2012, he won a competition for New York's Funniest Stand-Up and he also performed for the first time on CBS's "The Late Show with David Letterman". He first landed a job as a writer on "Saturday Night Live" in 2013, and the next year he worked as a correspondent on "The Daily Show" for one season before returning to "SNL" as the co-host of "Weekend Update."
Now, Che is a co-head writer of the NBC sketch show and he's co-hosting the Emmys along with Colin Jost, his fellow "Weekend Update" anchor.
Last year, Che told Fallon that he always felt bad that he "stiffed" Hilfiger, who he said he'd never seen since he ditched the freelance gig all of those years ago. On the "Tonight Show," Che even whipped out his checkbook and wrote a check for $1,000, made out to Hilfiger, in the hopes of squaring his debt.
"Just make sure you don't cash it until October 13," he joked.
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