The teenager who arrived at Easy Street that summer didn’t look like a future guitar legend.

“He was just a real kid,” recalled Mikel Ross. “Braves cap on, wide-eyed, showing off the van’s mobile TV and his Sega.” His name was Derek Trucks, and he was 12 years old.

Today, Trucks is widely regarded as one of the finest slide guitarists of his generation, a musician whose career has included the Allman Brothers Band, the Tedeschi Trucks Band, and multiple Grammy Awards. But on July 18, 1992, he was simply a teenager from Jacksonville, Florida, arriving in downtown Raleigh to play a small club on East Hargett Street. 

The club was Easy Street Cafe. And the booking itself came together with the kind of casual spontaneity that would come to define the venue.

“I put my hand over the phone and said, ‘Mom, do we want Butch Trucks’ nephew to come play slide guitar in the bar?'” said Ross, who assisted in booking bands at Easy Street. “She said, ‘Is Butch going to come?’ I said, ‘No, Mom, Butch is not going to come.’ And she said, ‘That’s all right, have him come anyway.'”

At the time, there was no reason to think the show would become a footnote in American music history. But Trucks was one of many musicians who passed through Easy Street during its short existence. Col. Bruce Hampton and the Aquarium Rescue Unit played there. Peter Rowan and Doc Watson came through. American saxophonist Maceo Parker, accompanied by The JB Horns, performed. One night, John Prine unexpectedly walked through the door.

Club co-founder Jim Bob Crites. Photo courtesy of Dierdre Shipman.
Club co-founder Jim Bob Crites. Photo courtesy of Dierdre Shipman.

For a brief period in the early 1990s—opening in April of 1991 and closing 21 months later, in December of 1992—a club that many Raleigh residents have never heard of managed to attract an outsized collection of talent.

The timing makes the story even stranger.

When Trucks stepped onto the Easy Street stage, downtown Raleigh had not yet become the entertainment district people know today. Kings was years away. Slim’s wouldn’t open for seven more years. Lincoln Theatre, then operating as a bar and internet café, had not yet emerged as a downtown music anchor. Much of Fayetteville Street remained dead after business hours.

“‘Downtown’ Raleigh had not come back to life yet,” remembered Andy Brown, a local musician who grew up in Raleigh. “The Fayetteville Street Mall at night was a ghost town. All you heard was the cuckoo of the crosswalks for the blind.”

Somehow, in the middle of that silence, Easy Street found an audience.

Easy Street Origins

If Easy Street’s guest list seems surprising, its origins were just as remarkable.

Top: Steve Jackman, Dierdre Shipman, Victoria Kerr, and Jim Bob Crites. Photo courtesy of Dierdre Shipman.
Top: Steve Jackman, Dierdre Shipman, Victoria Kerr, and Jim Bob Crites. Photos courtesy of Dierdre Shipman.

Owners Jim Bob Crites, Dierdre Shipman, and Victoria Kerr met through Raleigh’s counterculture scene, at Sadlack’s on Hillsborough Street. None of them had ever owned a music venue, but, convinced the city needed something aside from the loud dive bars they frequented, the trio took a leap of faith, handling all venue operations, from cleaning the toilets to working the bar and running sound.

“We provided the dream and the sweat equity,” Shipman recalled.

Crites handled the books, inventory and day-to-day operations. Shipman booked acts and cultivated relationships with touring musicians. Kerr managed the front-of-house experience while helping shape the club’s identity. Her daughter, Rainbow, supported the kitchen, and as the calendar grew, Shipman brought on local musician and Kerr’s son, Mikel Ross, to help with booking.

“And there was a fourth Beatle,” Shipman said. “Steve Jackman, a dear friend and architect who helped design the look of the place: purple walls, cushioned seating. We even painted the place ourselves.”

Sometimes, the owners themselves took the stage. 

“There was one last open mic night,” Ross recalled. “Harry Tueting, from Harry’s Guitar Shop, hosted it. It was the only time Jim Bob Crites ever took the stage during Easy Street’s entire existence. The two of them played ‘Landslide,’ and there wasn’t a dry eye in the house. It was the most vulnerable I ever saw Crites let anyone see him.”

Together the group transformed the large East Hargett Street building into something Raleigh didn’t have enough of at the time: a room built around live music.

Initially, Easy Street was conceived as a place where people could sit down, enjoy live music and have a meal. Blues, jazz, and acoustic performers formed the early backbone of the calendar before the club gradually expanded into rock, roots, and Americana. Word spread.

When Dark Star played Easy Street, said Brown, fans traveled long distances just to attend. The club quickly became a crossroads for musicians and music fans alike. Touring performers mixed with local acts. Friendships formed. Sometimes those encounters became stories.

When Dark Star opened for Col. Bruce Hampton and the Aquarium Rescue Unit, Brown recalled keyboard player Michael Thrower leaving his keyboard case open backstage. Instead of stepping around it, Hampton stepped directly into it. The muddy footprint remained.

“Michael revered it like an autograph,” Brown recalled with a laugh.

A night at Easy Street. Photo courtesy of Dierdre Shipman.
A night at Easy Street. Photo courtesy of Dierdre Shipman.

Prine Night

As Easy Street’s reputation grew, so did its network.

By then, Ross had joined Shipman in booking acts for the club while writing for the local music magazine Real to Real. After interviewing John Prine following the singer-songwriter’s April 8, 1992, performance at Raleigh Memorial Auditorium, Ross found himself chatting with Prine aboard the tour bus.

Before leaving, he made an offhand invitation. “Well, my mom has the club down the street, and I’m the booking agent. You should come by.”

He didn’t expect anything to come of it but about thirty minutes later, Clea, the doorman, knocked on his office door upstairs at Easy Street. “Hey man, there’s a big group of people here to see you.”

It was Prine and his entire band. 

“They showed up for the free beer that had been offered,” Ross recalled. “So I immediately dropped some pitchers on the tables and said, ‘Hey, you know, it’s open mic night tonight. Why don’t you sign up on the list?’ I was joking.””

But then:  “I’ll be fucker’ed,” Ross continued, “if Prine didn’t walk up and put his name on the list.”

Prine played six songs that night for what Ross still calls “the luckiest people on earth.”

“Everybody made up lies and said they were there,” he said. “There really wasn’t hardly anybody there. It was the open-mic crowd. They just happened to get John Prine that night.”

Photo courtesy of Dierdre Shipman
Photo courtesy of Dierdre Shipman

Easy Street had become exactly the kind of place its founders imagined. Financially, however, the venue was struggling.

As to why, the answer depends on whom you ask. Brown points to a downtown that still emptied after dark. Ross remembers a restaurant struggling to find enough diners in a city that wasn’t yet eating downtown. Shipman points to the slow erosion of ownership as investors were repeatedly asked for help keeping the venture alive. All three may be right.

“The place closed after its second year just as we were getting close to breakeven,” Shipman said. “Each time we needed a cash infusion to keep going, the three of us with sweat equity ceded more ownership to the investors until we ended up as minority shareholders.”

Before Easy Street closed, they made one last attempt to reinvent the club with an experiment called the Deep, an after-hours dance event that ran from 2 a.m. until sunrise. It represented a departure from the blues, jazz and Americana that had built Easy Street’s reputation.

Drink Small performs at Easy Street. Photo courtesy of Dierdre Shipman.
Drink Small performs at Easy Street. Photo courtesy of Dierdre Shipman.

“Some things were too progressive to live for long in an environment like Raleigh was at that time,” Ross reflected.

Among those working the door was a young Zach Galifianakis, years before he became a household name.  A 1992 Raleigh News & Observer piece captured the scene thusly: “Since the bar can’t serve alcohol after 2 a.m., ID isn’t required. For $3 anybody gets in. Well, almost anybody. Even Deep has its limits. ‘I doubt I would let a 7-year-old in,’ says doorman Zach Galifianakis.”

“What stands out to me are the relationships that lasted way past the club

dierdre shipman, easy street owner

Nevertheless, by New Years Eve of 1992, the experiment, and the venue, was done. Easy Street disappeared from East Hargett Street. But the people didn’t. 

“What stands out to me are the relationships that lasted way past the club,” Shipman said.

Rainbow Kerr met her future husband, Aquarium Rescue Unit drummer Jeff Sipe, at Easy Street. Shipman met her future husband there as well. “There are kids on the planet who wouldn’t be here without Easy Street,” she said.

Today, downtown Raleigh is filled with the restaurants, music venues, and nightlife that many now take for granted. When Easy Street opened in 1991, much of that simply didn’t exist. The building at 119 East Hargett Street still stands, broken into several suites for businesses. Most people pass it without realizing that a 12-year-old Derek Trucks once played there or that John Prine once wandered in for an open mic night. 

For 21 months, a handful of people with little more than a dream imagined a different future for downtown Raleigh. For 21 months, they were right. The city later followed. The culture came first.

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