Darryl Settles of Darryl’s Corner Bar and Kitchen

Settles entered the restaurant business in 1990, when he purchased Bob the Chef’s, a restaurant often referred to as “an icon,” “a landmark,” and “a South End institution” at the corner of Columbus Avenue and Northhampton Street. Back then, he was a sales and marketing executive at Digital Equipment Corp. who imagined that he would just “come in on Fridays and pick up my money.”

Eventually, Settles turned Bob the Chef’s into a successful, profitable business. During the 17 years he owned the restaurant, Settles renovated it twice, changed the name to Bob’s Southern Bistro, and added live jazz.

His restaurant became so popular that it attracted a number of celebrities. According to Settles, actor Forest Whitaker took his wife to Bob the Chef’s on their first date, during the filming of ‘Blown Away’ in 1993. He says the members of New Kids on the Block dined in the back corner of Bob’s three or four times a week for five years. And he remembers the time singer Natalie Cole’s limo pulled up in 1995 and she stepped inside to order a chicken and rib combo before a flight.

Settles sold Bob the Chef’s in 2007 but retained ownership of the building. His reasons for parting with a restaurant he had owned for so long were numerous. They included the imminent arrival of his second child, increasing time spent on the Beehive, and numerous other commitments. Although he is known best as a restaurateur, Settles is also a co-founder of WiSe Urban Development, a real estate development company… Additionally, his civic activities range from the BeanTown Jazz Festival, which he founded, to the Massachusetts Convention Center Authority.

Malcolm Aalders purchased Bob’s from Settles and transformed it into Circle Plates and Lounge, an upscale French bistro. After less than six weeks in business, he closed Circle and sold it to Ziad Chamoun, who opened The Stork Club in its place. The Stork Club, which offered an eclectic menu of French, Southern, and Asian cuisine, lasted 10 months. At that point, Settles decided to take the location back under his wing and opened Darryl’s Corner Bar & Kitchen.

“Every day I would hear, ‘We need it back, we need it back.’ I knew it was a safe move. I knew I would have a following,’’ Settles says.

Darryl’s offers patrons a chance to listen to great jazz, but still be able to carry on a conversation. The décor is sleek and balanced, with instruments mounted above the bar. Paintings and black-and-white photographs line the exposed brick walls above comfy banquettes…