It's rare for Justin Bieber to crack a smile, let alone shed a tear. But during a tribute to the late singer Christina Grimmie at a concert in Winnipeg, Canada on Saturday, he broke down. In a performance of his tour's title track "Purpose," he sang "Grimmie, can you hear me?" while lying on the ground. He then wiped tears from his eyes before he got up. Biebs became close with Grimmie, a former The Voice contestant, while she was touring with Selena Gomez, according to Seventeen. Grimmie was shot and killed after she opened for rock band Before You Exit in Orlando, FL Friday night. Other celebrities including Demi Lovato, Nick Jonas, and Meghan Trainor grieved her loss. Maroon 5's Adam Levine even offered to pay for her funeral. The singer clearly left a lasting impact on her colleagues during her 22 short years.