BRATTLEBORO — Jesse Lepkoff's musical path is rich and peripatetic. From performing with the Boston Camerata to writing and performing bossa nova, Marlboro's own music man is now headed to Memphis to compete in The Blues Foundation's 2023 International Blues Challenge (IBC) on Jan. 24-28.
No minor deal, Lepkoff recently earned this ticket at a competition of the Vermont Blues Society (VBS) in Montpelier. Having landed at the top of the solo performers' competition there, he's moving on to the next level and will compete in Memphis.
To prepare, Lepkoff has gathered five fellow area musicians for a Blues-A-Rama on Sunday, Dec. 4 to benefit Turning Point of Windham County in Brattleboro and to help fund his own trek to Memphis.
One can hear local blues legend Scott Ainslie with VBS solo laureate Sonny Lowdown, as well as Samirah Evans, Rob Freeberg, Greg Burnell, and Lepkoff - each in a short set - before closing with a group jam.
A talented lineup
Among these local musical luminaries, Ainslie, on a variety of stringed instruments, revels in roots music and has traveled, performed, and taught extensively in that realm digging, especially, into African and European roots of American music and culture.
With six solo CDs, Ainslie maintains an active recording, performing, and teaching schedule that carries him around the country, to Canada, and to Europe. He has received numerous awards and grants for documenting and presenting traditional music.
Known for his country blues, guitarist/vocalist Sunny Lowdown represented Vermont in the same competition in 2020.
Only 16 when he played his first professional gig backing John Lee Hooker, he's since worked with Howlin' Wolf's guitarist, Hubert Sumlin; Muddy Waters' pianist, Pinetop Perkins; Chicago blues legends Otis Rush and George “Wild Child” Butler; and Fat Possum Records' recording artists R.L. Burnside and CeDell Davis, among others.
Vocalist Samirah Evans' musical style is heavily influenced by the sounds of New Orleans, where she was one of the city's most in-demand singers before moving to Brattleboro after Hurricane Katrina. Her 1990 debut at the New Orleans Jazz & Heritage Festival began a stint of 15 years performing there. She's since been touring North and South America, Europe, and Asia, sharing stages with a multitude of New Orleans notables and legendary artists.
Evans has made three CDs as leader, the third of which, Hot Club, was recorded live at the Vermont Jazz Center with her band, Samirah Evans and Her Handsome Devils. Evans is dedicated to perpetuating indigenous American music through projects she curates as well as through teaching.
Trumpeter Rob Freeberg taught for 30 years at New Rochelle (N.Y.) High School where he was director of bands. Leader of various jazz bands over the years, Freeberg was selected as guest conductor for several all-county and regional music festivals in New York and has performed and recorded as a freelance trumpeter in the metropolitan New York City area.
Since moving to Vermont, Freeberg has become active at the Vermont Jazz Center, directing the VJC Sextet and the Big Band. He teaches at The Putney School and co-directs the Jazz Workshop at Brattleboro Union High School.
Guitarist Greg Burnell teaches music at Vermont Academy, The Putney School, The Academy at Charlemont, and The Greenwood School. The leader and a founding member of the Jacksonville Blues Band, Burnell has performed locally and regionally for the past 40 years as a solo artist, in duos and trios, and in many different full band configurations.
Why the blues?
At a young age, Lepkoff, a singer and songwriter, was attracted to early blues and jazz musicians such as Mississippi John Hurt, Lead Belly, Ma Rainey, and Bessie Smith, teaching himself many of their songs by ear. He recalls that his father would listen to a wide collection of LPs - an ample number of blues records among them - and young Lepkoff would listen avidly.
“Lead Belly was one of the first I remember, “ he recalls. “My brother and I were totally taken by this stuff. It was fantastic.”
At The Longy School of Music and New England Conservatory, Lepkoff took up baroque flute and landed a spot with a highly acclaimed early music ensemble, the Boston Camerata.
But eventually, he went back to guitar and grew ever more interested in early jazz and blues - aiming beyond the standard 12-bar blues formula, exploring sophisticated harmonies, and writing his own compositions.
“I'd written all these blues songs, then I heard about the competition,” Lepkoff says.
He sent cuts in, and then “all of a sudden I was in front of an audience and judges were scrutinizing all I was doing - originality, stage presence, vocals, guitar work, harmonies.”
“Even before all the contestants played, people were saying to me, 'You're going to win it,'” he says. And he did - though that moment, for Lepkoff, was unexpected.
At the Memphis competition, Lepkoff will have 25 minutes to play in the quarter finals on Jan. 25 and 26 - and it has to be exactly that duration, or he risks losing points.
If he makes the cut, Lepkoff will advance to the semifinals on Jan. 27 and to the finals on Jan. 28.
Lepkoff is looking forward to “rubbing elbows with folks who're into the blues, hearing a lot of music, and maybe meeting people who are into blues like I am.”
“Maybe finding collaborators, inspiration,” he says.