Local Roxbury Artist Cakeswagg Takes the Orange Stage at Boston Calling 2024

Photos by Payton Cavanaugh

By Payton Cavanaugh

“That was a dream of mine, and it just happened,” said Cakeswagg. 

Local Roxbury artist Cakeswagg brought the heat to the Orange Stage at Boston Calling on Saturday May 25. She demanded deserved attention with her captivating performance. 

The Orange Stage brings the festival back to its roots as it provides a space for local Boston artists to showcase their talent. For Cakeswagg, performing at this festival meant so much more than just the opportunity to be on the lineup.  

“This was actually my first time at Boston Calling,” said Cakeswagg. “I’ve always wanted to go, I just never had the opportunity.” 

Cakeswagg has been releasing her music for about six years, but her rapping career goes all the way back to making beats on the school bus as a teen. 

She’s always had a love for performance, graduating college in New York for theater. She said it was after graduating that her friends really started to push her to get back into music. It all began when they started a bartending business where they encouraged her to make them a theme song. 

“I made the song called “Buzz Up With the Barbies” because that was the name of our bartending group…dropped it, and it just went crazy,” said Cakeswagg. “After that, everyone was expecting more music from me.” 

From then on, Cakeswagg began writing and releasing her music. However, her week at Boston Calling was not simply about her as she made sure to uplift the next local Boston artists around her. 

As a performing arts teacher, Cakeswagg saw the opportunity to perform Boston Calling as a chance to share the spotlight. Her set was a culmination of talent as her DJ, DJ WhySham, teaches at the same school as her while her dancers are high school students from Four Star Dance Studio where Cakeswagg’s long-time friend and colleague, KiKi, choreographs. 

“Right on the cusp of Dorchester and Roxbury, there's so much culture in that specific neighborhood,” boasted Cakeswagg. “We kind of came into this knowing we’re continuing a legacy…that was really embedded in us before we even did it so it was just a really powerful moment to take all of this history and beautiful Boston musicianship that we've gotten to grow up in and really bring that on the stage.”

Looking out into the crowd, Cakeswagg was surrounded by so much support. Even some parents of her students were able to make it.

“We know so many young kids that are looking at us, really hoping for us to succeed,” said Cakeswagg, “especially coming out of Boston, coming out of these urban areas, it's inspirational. It's like, you know what? If my teacher did it, I know I can do it.”

Cakeswagg expressed her gratitude for all of the artists she was able to see perform—from Boston-based artists like Billy Dean Thomas and Tori Tori, to headliners like Ed Sheeran and Megan Thee Stallion. 

“They remind me so much of myself in the sense that we’re so meticulous about our artistry,” she said.

Even though Cakeswagg performed among artists of varying popularity, she said she really appreciated the way she was treated throughout the weekend. 

“One thing I really appreciated about Boston Calling is that even some of us who are smaller artists, they made us feel big… they not only took care of us, but our entire team,” said Cakeswagg, “I felt like they wanted me here, and they’re treating me like my artistry matters to them.”

While Cakeswagg fulfilled one of her dreams on that stage, this is just one big milestone in her path. This summer she is busy finalizing many projects, including her new album. 
To stay up to date with Cakeswagg, you can check out her Instagram here.