Former Bob the Chef’s and DCBK managers, Nia Grace now owner of Grace by Nia Restaurant, Luther Pinckney, Pearl Restaurant creator and Shawn Hunter, CEO of International Kitchen and consulting for Orchid 7 Fusion Bar and Grill reminisce at the gathering.

Nina Williams, Billy Willis, Rose Aruta, Allen Settles, Candace Burns and Kevin Scott share stories from their time at the legendary restaurant.

More than 30 former employees and community members gathered on Monday to celebrate the 35th anniversary of the new ownership of the soul food restaurant formerly known as Bob the Chef’s. Located at the edge of Roxbury and the South End, the restaurant opened its doors in 1957 under the ownership of Robert and Dottie Morgan; in 1990, entrepreneur Darryl Settles bought the establishment.

In the 35 years since, the restaurant has been reincarnated many times. Notably, Bob the Chef’s has also served as a cradle for other Boston restaurateurs, especially Black-owned restaurants. In 2010, for instance, Settles renamed it Darryl’s Corner Bar & Kitchen (DCBK). In 2018, DCBK came under new ownership: Nia Grace, of Seaport’s renowned Grace by Nia fame, and who had been a consultant with DCBK since 2015, took over.

Grace closed Darryl’s Corner Bar and Kitchen at the end of 2023, saying the establishment was going to go through a rebranding. After more than a year, it seems the restaurant’s doors may finally be ready to reopen under the name Uptown Social.

Monday’s gathering was an unexpected celebration for Settles. “I actually did not realize it was an anniversary,” said Settles, who is now a real estate investor, developer and CEO/president of Catalyst Ventures Development. The idea was to have a holiday get-together with former employees, but it was Banner publisher and co-owner Ron Mitchell who called Settles’ attention to the anniversary. Seeing the gathered crowd, “We were so excited, and that made me feel really, really good and proud,” Settles said.

Bob the Chef’s offered Southern soul food and live entertainment, a tradition that DCBK continued. The combination made it a lively and friendly atmosphere and a popular neighborhood hangout.

Settles said he never could have imagined celebrating 35 years of Bob the Chef’s restaurant.

“I’ve had over 1,000 employees during that time frame,” he said. “You just never think that [the] number would be so high, but it is because of the turnover [in the restaurant industry] and so you realize how you impacted so many different individuals over time.”

One such former employee is Luther Pinckney. He was the first manager of Bob the Chef’s under Settles and went on to become one of the founders of The Pearl restaurant, originally in Dorchester and now with a location in Allston as well. He also helped establish Ester, a restaurant that operated in Dorchester from 2014-2018. Today, he is the community engagement specialist for BEST Hospitality Training.

About his time at Bob the Chef ’s, Pinckney said, “It’s definitely been a linchpin of our community [and] definitely a high mark on my personal resume.”

Another former employee, Nina Williams, now works as the director of the Student Service Center of UMass Boston and was present at Monday’s celebration. She worked under Settles back before he changed the name to DCBK.

“Even though it was bad weather, a lot of people made it out. I saw people that I hadn’t seen in a minute that I worked with,” she said, adding, “The anniversary just brought us back together. We were able to reminisce and celebrate people’s accomplishments and celebrate Darryl and what he’s done for the community and for the city of Boston,” she said.

Shawn Hunter, who was also at the anniversary gathering, served as a managing partner for DCBK and said that one of his favorite moments working at Darryl’s Corner Bar and Kitchen was the Jazz Brunch.

“I always enjoyed the jazz brunch — just [seeing] the raw talent of the Berklee [College of Music] professors and [the] different talent around the city, while having an all-you-can-eat brunch was always one of my favorite[s],” said Hunter, who is now CEO of the food service company International Kitchen and consults for Boston-area restaurants including Orchid 7 Fusion Bar and Grill. “I would go there at 10, before it got busy, and just watch the crowd roll in, roll out, and leave happy.”

Grace, whose restaurant in the Seaport made her the first Black woman restaurant owner in that neighborhood, has similar memories. “Some of my favorite nights might be New Year’s,” she said. “We would often attract regulars for those nights and it was always just good while you’re working, to be in good company and know that you really just have ‘family’ in the room with you.”

Hunter recalled that Settles spoke to him about his desire to bring about change to Boston’s restaurant scene. When he asked him what skills he could bring to the company, he said Settles replied, “I want us to teach the Black and brown restaurants how to be more profitable and be more sustainable, that we need more of us in this city.”

To Pinckney, the fact that the restaurant — through all its various forms — has been able to weather the transition of time and ownership, but stay in the Black community, has been vital. “I think it’s important to honor our history and try to rebuild it as much as possible,” he said.

The recent celebration also reminded Settles that there were very few places where people of color could go and have a good time when he became owner of Bob the Chef’s back in 1990.

“I am excited and happy that some of my former employees have increased those options,” he said. Others in the community should similarly celebrate the accomplishments of those who have gone on to open their own establishments, he said, especially given the harsh realities of the restaurant industry.

“In the hospitality world, it’s mostly a labor of love. …Very few really make real money,” he said. “People who choose this profession are making sacrifices for others to enjoy themselves. We owe it to those individuals to support them and be by their side.”