“You’ve got a better chance of getting in there than I do, I’ll tell you that,” he said to one person during his busking experience, which he also streamed on Facebook Live. An hour in, thousands of people were watching, and a small handful of fans surrounded him on the street.

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“Finally made it, guys, big show,” he deadpanned. “They were all out of seats, I couldn’t get a ticket. So I thought I’d come down here and play some country music, since we’re celebrating it this evening in Nashville, Tennessee.”

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Simpson, who won a Grammy this past February for best country album, appeared to place the trophy inside his guitar case on the street. He was also nominated for the coveted album of the year prize, though his “A Sailor’s Guide to Earth” lost to Adele’s “25.”

While he was outside, Simpson had a sign that read “I don’t take requests but I take questions about anything you want to talk about because fascism sucks.” That just might be a dig at the CMA Awards media guidelines released last week, which stated reporters could be kicked out if they asked country singers about sensitive topics such as the Las Vegas tragedy, gun control or politics. After intense backlash, the CMA apologized and lifted the restrictions.

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Another sign stated “‘Struggling’ country singer … anything helps. (All donations go to the ACLU) God Bless America.”

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Though Simpson’s latest album went No. 1 on the country Billboard charts, he’s also considered Americana music and overlooked by mainstream Nashville — and his sound is far from what fits on commercial country radio. Simpson has also made it clear that he’s no fan of the genre’s trophy ceremonies. Last year, he blasted the Academy of Country Music Awards after executives created a “Merle Haggard Spirit Award.”

“If the ACM wants to actually celebrate the legacy and music of Merle Haggard, they should drop all the formulaic cannon fodder bull—- they’ve been pumping down rural America’s throat for the last 30 years along with all the high school pageantry, meat parade award show bull—- and start dedicating their programs to more actual Country Music,” he wrote on Facebook.

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Simpson added he was well aware the industry would “blackball” him after his comments, though he added, “I’m not sure how you can blackball somebody you don’t acknowledge in the first place anyway. Yet, even though they mostly go out of their way to ignore artists like myself and Jason Isbell, I assure you they are more than aware of our existence. They are also well aware that we don’t need them. Our last albums went to #1 without any help from the Mainstream Country Music establishment…and our next albums will too.”

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Meanwhile, on Wednesday night, Simpson fielded all kinds of questions, including who he wanted to win a CMA. He said it would be great if his close pal Isbell won (nominated for album of the year), and that if he had to choose, he was also rooting for Chris Stapleton, Miranda Lambert and Keith Urban.