Meet the alumnus behind our hit Giving Day theme

Inked on Ryan Tobbe’s chest is a tattoo of his life’s mantra: make people smile.

“It’s my, perhaps, overly simplistic, answer to a world rife with anxieties and unsolvable problems,” he said.

“So, while I may not be able to stop war, or end world hunger, I can make a concerted effort to make people smile.”

Years ago, on a trip to Washington D.C., the Cleveland-born rapper took to the streets to perform. 

“I ended up making up a song for a recently widowed woman who had lost her husband of 50 years,” he said.

“We both cried and hugged at the end, and she told me that it was like her husband was back.”

Every interaction might not end in tears or an embrace, but it’s the sort of impact, Ryan (aka TobyRaps) hopes to bring with whatever he creates — joy and hope with a bit of playfulness. 

On his 2018 debut album aptly titled “Make People Smile,” he muses about best friends and the ephemeral nature to life on intro track. We’re here for a good time, not a long time, he says as much. So, we might as well “have some fun in the meantime.” 

Once you meet him in person, you'll pick up on how likable a guy he is and why his brand of music is what it is. He’s care-free. And “ridiculously unfraid,” as his producer and close friend Chris DiCola said. When he first laid eyes on him, Ryan was performing at an open mic “wearing a blue blazer and pajama pants.” The two quickly became fast friends and collaborators. So, yes. Ryan is magnetically endearing. With bars on bars at the ready.

He honed his chops as a student at Cleveland State, freestyling exclusively for the girls in the Euclid Commons dorms  — dubbed the “EC Floor Tour” — and laying the foundation for his eventual three-year stint as a Cleveland street performer, where he’d ask passersby for topics and create impromptu songs on the spot. 

“It’s not job for everyone,” he raps about busking in “Make My Rent” on his debut.

“But it’s a job for some.”

Eventually, it became a job that took its toll…even for Ryan. So, he turned his sights on the studio and creating that first album, drawing inspiration from his time as a street performer.

After earning a bit of buzz, he headed west for the glitz of Los Angeles, recorded a second album, “Make More Friends,” launched a tour and eventually landed back in Cleveland during the height of COVID-19. He noted how accessible Cleveland made being an artist, as in, he could afford his rent, eat and invest in his craft. Plus, he noted how generous the music community can be. 

Ryan followed up his second album in 2021 with his third “Make Yourself Happy” and is working on his fourth, Grow Up, where he explores how embracing the responsibilities of adulthood can make you — what else — happier and that you can keep your childlike wide-eyed wonder of the world. 

“The more you take on, the more you can be proud of,” he said. 

“And you’ll find that the creativity thrives in that situation.”

He’ll be appearing at the House of Blues next month, then at CODA in Tremont in April with other shows planned for the summer, spreading the good news of happiness.

Perhaps we should all pick up that mantle in our own way. 

“If we did that,” Ryan said. “The world of tomorrow might just be a brighter one.

Check out the theme song he wrote for Giving Day on Thursday, February 29.

And follow him on Instagram @tobyraps.