The 27-year-old singer–songwriter and Jimmy Fallon, 45, conducted the first interview segment while both painted portraits of each other.
Demi did the whole interview via video chat while staying at her mother’s house in Los Angeles.
Jimmy mentioned that Demi had gotten back into practicing her painting skills, and he showed off an admirable array of small paint tubes, despite his lack of art experience.
‘I’m really not good, so I’m really kind of scared. I want to be you!’ he said, though Demi downplayed her own talents.
Once the two had gotten their brushes ready, Jimmy complimented her on her show-stopping Grammys performance Anyone, which came the same day that Kobe Bryant and his daughter Gianna were killed in a helicopter crash.
‘I always hoped that if I stepped back on stage, that would be the song I would sing,’ Demi replied after noting how nervous she had been.
‘I got emotional because I saw my family, my mom and my sisters, sitting in the front row,’ she explained.
‘That to me was really really special, because the last time we all listened to that song together was when I was in the hospital, and I didn’t know if I was going to sing again.’
The Sorry Not Sorry singer got a compliment from Jimmy on her musical impressions, including her popular Cher singing voice, which inspired her to try out a new non-singing impression.
She had the comedian in stitches after she impersonated her favorite Schitt’s Creek character Moira Rose, played by the great Catherine O’Hara.
Once it came time to reveal their paintings, Demi showed off a stylized portrait of Jimmy that accentuated his grin and his elastic features.
‘You are so good, I want to buy that!’ Jimmy shouted after he got a look at his visage.
Despite claiming to be a novice, Jimmy’s painting was a surprisingly realistic version of Demi’s face, though he ran out of time to finish the eyes.
In the second segment, Jimmy gave Demi a platform to talk about the importance of caring for your own mental health needs.
‘We’re alone with out thoughts right now. Some of us are at home alone, some people don’t have family with them, they don’t have pets, and so it’s really just them and their minds,’ she said.
‘Those voices in your head can get really loud. I call them roommates. And the roommates in your head can be just as annoying as a real roommate.’
Demi mentioned that her manager Scooter Braun had started a group FaceTime group with a new guest of honor every night to keep people engaged.
The first time she got on the call she found herself face to face with former President Bill Clinton.
Demi wrapped up her appearance with a stunning performance of her newest single I Love Me, which showed just how great her vocals were, even over a video chat connection.