Gordon Sterling on guitar.
Gordon Sterling on guitar. Credit: Darrow Montgomery

Gypsy Sally’s is hopping the night before America celebrates its 242nd birthday. The club is staying open an hour later in light of the holiday, which is more than fine for the nearly 100 people here to jam.

Twice a month, the Georgetown club hosts a Tuesday night jam session. The hang is loose, the beers are frothy, and friendships are forming, but it’s the spontaneous invention on stage that brings everyone here. Jam sessions are a time-honored tradition in music circles, but recently there’s been an increasing number of open jams at venues around the DMV, and they are energizing the local music scene. High quality bands are forming at an astonishing pace as a result, to the point where people might look back upon this time in the same way that people view the harDCore scene of the 1980s.

Regular jazz jam sessions around the District are nothing new—Wednesday nights at Mr. Henry’s and the DC Jazz Jam on Sundays at The Brixton are two of the best longtime ones. Gypsy Sally’s serves as something of a hub for this new wave, with spots like Bossa Bistro + Lounge in Adams Morgan, The Wharf ’s Pearl Street Warehouse, Villain & Saint in Bethesda, and Epicure Café in Fairfax all hosting open jams. Going to one of these sessions is not only an engaging way to spend an evening, even if it’s just to observe, but it also gives insight into the anatomy of a vibrant music ecosystem.

If there’s one person who is the central figure in all of this, it’s guitarist and vocalist Gordon Sterling. The 40-year-old musician was born in Queens, New York, to Jamaican parents and moved to the D.C. area when he was 10. Sterling picked up a guitar at 15, formed a band, The Ordinary Way, at 18, and hit the road with the group at 21. The Ordinary Way toured nationally for 10 years, getting far in the jam band circuit before breaking up. Currently, Sterling plays with Nappy Riddem, which he joined several years ago, leads Gordon Sterling and the People, and is part of singer Mary-eL’s ensemble.

Sterling began running jam sessions at the now-defunct Iota in Arlington in 2016 with Sean Gotkin, who currently does sound at Black Cat. “Something really just magical happened there,” says bassist Neel Singh, who runs Wednesday night jams at Villain & Saint. But that magic wasn’t meant to last, as the venue shuttered exactly one year after the jam sessions started.

A few months after Iota closed, Sterling moved the session to Gypsy Sally’s, where attendance has since exploded. Sterling estimates that about 70 percent of the spectators and musicians that come are regulars—the rest being new faces and curious ears.

“It’s almost like a Field Of Dreams situation where if you build it they will come,” Sterling says.


Sterling’s goal when he started organizing jam sessions was to eliminate what he calls a “crabs in a barrel mentality” that he felt was rampant among local musicians competing for a limited number of gigs. From the beginning, he wanted to make sure that the environment he created would be inviting and accessible, which in turn could lead to a feeling of camaraderie.

“There’s enough food for everybody to eat,” he says. “We were adamant that it was a ‘leave your ego at the door’ kind of situation.”

Sterling is the public face, but he works with bassist Patrick Cheng, who leads Shamans Of Sound, in addition to playing bass with Nappy Riddem and on occasion with See-I and Black Masala. Cheng credits the jam session’s success, in part, to the basic nature of the area.

“We’re right next to a bunch of suburbs, so it’s a bunch of pretty well-off children with a lot of time on their hands, and then they pick up a guitar and that’s their drug,” he says. “You don’t have to impress somebody to be part of the scene.”

The Gypsy Sally’s session takes place on two Tuesdays every month. Sterling announces the specific Tuesdays via Facebook prior to the start of the month, believing that the irregularity helps maintain interest. The house band provides backline amplification, drums, and keyboards.

Jams are of two types: bucket jams and se- lect jams. With bucket jams, there are literal buckets at the foot of the stage with “talents” written on them (bass, vocals, drums, etc.). Sterling picks a name from each bucket at random and those called play on stage together. For the select jams, people come to the venue with a specific lineup in mind and submit them to Sterling. The night alternates between bucket jams and open jams.

“It’s like herding cats,” Sterling jokes.

In terms of maintaining a certain level of performance, the musicians themselves tend to police anyone who tries to show off and hog the spotlight. Sterling has only once had to pull someone off stage who was not as far along in their craft for jamming.

“I had to handle it gently and I felt horrible about it, but it had to be done,” Sterling recalls. “Luckily, he was gracious and I bought him a drink. We also did end up finding a jam where he could play a song he knew.”

That one instance notwithstanding, the level of musicianship on display will impress even the most casual listener. Mike Sains is a scratch DJ and regular at Gypsy Sally’s, and he spins weekly at the Villain & Saint jam.

“The understanding is that we’re all good so you better come correct when you’re on stage,” he says. “It’s a real ego killer is what it is.”

Each jam session also tends to take on the personality of its organizer, thus differentiating the experience for the listener. For example, at Singh’s Wednesday night jam, which is more intimate than the one at Gypsy Sally’s, musicians sign up with him and then he curates the lineups that perform.

“Gypsy Sally’s is the big house, it’s just on a grand scale,” says Singh. “Sometimes you go and you won’t get to play, it’s just a numbers game.”

While the term “jam band” can have a specific and often negative connotation to many people, these sessions do not limit themselves to any particular genre. This new crop of musos either see that term as an anachronism or have a broader view of the jam scene than the one that existed 20 or more years ago.

“First of all, it was only hippies. It was around the [Grateful] Dead or Phish,” says Sterling about the jam band scene of his youth. “There wasn’t a lot of diversity in the scene back then. Now, I feel that it’s a broader, smarter scene.”

At a typical Gypsy Sally’s jam, singers, MCs, and instrumentalists of all stripes and backgrounds converge. Sains views these sessions as a way to grow as an artist.

“The question for me as a DJ was, ‘How do I incorporate what I do with what these sometimes classically trained musicians do?’ so we can create the musical conversa- tion together,” he says.

After describing his approach to “tonal percussive manipulation” and fitting into varying styles, Sains admits, “All of the stuff I just said to you, I wasn’t able to articulate two years ago.”


An explosion of bands has come out of the sessions, with dozens forming as a result. Several of them performed at a recent, highly successful Planned Parenthood benefit at Black Cat. Not only have the number of bands grown, each one of them now has a readymade audience.

This reflects the sense of community that brings people back to Gypsy Sally’s or Epicure Café, or Villain & Saint week after week. There is no real distinction between those on and off stage.

Sterling walks around the club offering greetings and bear hugs to everyone he meets. The absence of a velvet rope and the living room atmosphere provide a holistic view of the DMV’s music scene. The inclusivity is intentional and aimed at people of all backgrounds.

“I think sometimes when you’re a woman you deal with stuff that’s a little different because you kind of have to have your guard up,” says Stephanie Kaiser, a keyboardist who leads the band Skaii, which grew out of the sessions. “Most of the people I’ve worked with have been really great. I think encouraging women to have a place in improvisational music is something we’re always kind of working on.”

Sandi Redman, a federal contractor who spends multiple nights per week in local music venues, comes back for the people as much as she does for the music. “All of these folks here have becomes friends of mine. We’re a crowd of at least 200 people,” she says.

Redman has taken it upon herself to document the growing community via her YouTube channel. Similarly, Will Urquhart is an audio-visual professional who streams and archives all of the jams he attends on DC Music Review. He looks to the PhishOD app for inspiration, which is an archive of Phish performances going back to the band’s earliest shows from over 30 years ago.

“There are all these phenomenal musicians and we have no idea where any of them are going,” Urquhart says. “There might be some kid sitting on his phone 30 years from now listening to the earliest recording he could find of this musician he’s really into.”