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Smith, 20, treated fans to a performance of her new album with a virtual concert on Facebook Watch, posted on the platform last Friday.
It appears to have been recorded at least number of weeks ago, as Smith has since shown off her new hairdo on Instagram - in one snap posing alongside mum Jada Pinkett-Smith after encouraging her to follow suit.
"Willow made me do it because it was time to let go," her mother wrote.
But now we get to see the exact moment Smith took the plunge, which just so happened to be while she was performing.
Towards the end of the online gig, Smith steps back from her microphone and grabs a guitar, before sitting down on a chair that had been brought on stage by someone - who also proceeds to get out some hair clippers.
Smith then plays along to the band's rendition of 'Whip My Hair', sitting back slightly as she has her afro hairstyle shaven off.
She casually continues to shred on the guitar as large chunks of her hair fall to the floor, eventually looking up to show off her new look.
Earlier in the video, she explains: "My favorite song in the set right now - just because of how it feels to sing - would probably have to be 'Whip My Hair'."
We then see rehearsal footage, as Smith continues: "When I made 'Whip My Hair', I didn't really know that it was an important thing because I was just expressing my joy, and I was just expressing myself.
"For so many years I just kind of spiralled, and didn't really understand that and wanted to push myself away from that. Without having that understanding, I'm pushing away the very thing that is who I am.
"I want to be promoting positivity, I want to be promoting expression, and I feel like 'Whip My Hair' was just a huge encouragement to people to just be themselves and to help others to the same."
Smith then says: "I'm thinking about shaving my head during the 'Whip My Hair' performance. This is going to be my third time in my life shaving my head.
"I'm always shaving my head at monumental times in my life when things are really changing and this is definitely one of those moments."
Back in May, Smith revealed that she struggled when 'Whip My Hair' first debuted, having been so young when it was released.
During an episode of Red Table Talk, Smith told her mother and grandmother about how she had self harmed at the time, saying: "[I] Totally lost my sanity for a moment there. I never talk about it because it was such a short, weird point in my life, but you have to pull yourself out of it.
"I honestly felt like I was experiencing so much emotional pain, but my physical circumstances weren't reflecting that."
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