Last summer, Taylor Bennett played something like 30 shows, including many of America’s biggest festivals. Due to the COVID-19 pandemic, summer 2020 has obviously been very different. That’s one reason the Chicago rapper and singer was so excited to perform Thursday (Sept. 3) as part of Billboard’s Live At-Home concert series.

Presented by Mercedes-Benz, the midday livestream enabled Bennett to connect with fans for 30 minutes and — just as importantly — raise money for the charity of his choice. Bennett selected Lost-n-Found Youth, a nonprofit that supports homeless LGBTQ youth in Atlanta.

“Lost-n-Found is an amazing organization,” said Bennett, who has a long history of working on behalf of both homeless youth and the LGTBQ community. “Shoutout to them and everything they’re doing. I really appreciate you guys.”

Backed by DJ and multi-instrumentalist Dwayne Verner Jr., a.k.a. DJ Verner, Bennett served up a mini-set of old, new, and unreleased songs. He opened with his latest single, “Good Guy,” which dropped back in February. Looking gym-ready in blue shorts and a matching T-shirt, Bennett switched nimbly between singing and rapping, playing to the camera as if he was rocking a festival crowd.

Next, Bennett slowed things with his 2015 ballad “Dancing In the Rain,” then kept it old school with another throwback, “Broad Shoulders.” “Reach for your goals,” sang Bennett on the latter as he closed his eyes, threw his head back, and made a fist.

Finally, Bennett premiered his forthcoming single “Be Yourself Pt. 2 (Sunset Falls),” which arrives September 19. It’s one of many new jams he’s cooked up during quarantine. “I’ve been having a lot of time to think,” said Bennett. “But one thing I’ve never thought to change is who I am. And if anything, this time has taught me to be myself.” The power of that realization was evident as Bennett sang the song’s uplifting hook: “That’s alright, I’ll always be me.”

In the Q&A that followed, the noticeably buff Bennett revealed that his favorite quarantine activity is working out. He said his decision to focus on fitness stemmed from becoming a new father in 2018. “When you have a family, you’ve got to be the best man you possibly can,” said Bennett, relaying a lesson he learned from his own parents.

Another fan wanted to know how Bennett, who’s openly bisexual, celebrated Pride Month in the absence of Chicago’s annual parade. “I really just had my own Pride,” said Bennett, adding that he treated himself to some ice cream. “It’s about celebrating who you are. I feel like I did that. I had a great time.”


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