Copyright 2018  Sgt. Billy Productions







Billy O’Brien grew up in Wakefield, Massachusetts and became interested in music at the age of 10 when he bought his first Silvertone guitar from Sears & Roebuck Company.  He took some guitar lessons and before long, young Billy was a "RockaBilly."


While in high school, Billy worked as a character actor at Pleasure Island in Wakefield.  Billy and his friend Lou Ciarfella played Indians and soon met Cowboy Rex Trailer. They were hired to appear with Rex and Pablo at personal appearances and eventually played characters on “Boomtown.”  Billy was working double shifts for Rex as an actor by day and pooper scooper by night.


After high school, Billy transitioned into folk music. He and some friends moved to Beacon Hill in Boston and played the local  coffeehouse circuit, which featured Bob Dylan and Joan Baez. It was around this time Billy discovered the banjo.  He bought Pete Seeger’s banjo lesson book and taught himself the banjo, which would become his signature sound.


In 1963, Billy enlisted into the U.S. Army. He spent the first part of his active service in the Republic of Korea. There he won several talent shows and ended up in Special Services in the Bayonet Choral touring the Orient. His folk group, "The Wanderers," made several TV appearances on AFKN (Armed Forces Korea Network) and played at Officers' and Enlisted Men's Clubs.


After completing his tour in Korea, Billy's horsemanship was about to be put to the test. He was assigned to the Cavalry unit of the 3rd Infantry Division (The Old Guard) as a member of The Honor Guard at Fort Myer/The Arlington National Cemetery in Washington, D.C. Billy had the honor of being a section sergeant in charge of the horse drawn caissons carrying fallen brothers and sisters, lost to Vietnam, to their final resting place.


While off duty Billy honed his performing skills by singing in and around the D.C. area in various coffeehouses and clubs, such as "The Cellar Door."


In 1966, Billy was honorably discharged with the rank of Sergeant––and Sgt. Billy was born.


Sgt. Billy returned to New England and enrolled at Berklee College of Music in Boston.  He set to make a career as an entertainer and called his friend Rex Trailer. Rex and sidekick Pablo, played by Dick Kilbride, introduced him to an agent and he was soon recording jingles and performing with Rex and Dick at every chance.


After Dick Kilbride passed away in 1967, Rex worked alone for a while and eventually started looking for a new sidekick to share the bunkhouse.  Terrence Currier joined the cast as “Cactus Pete” and “Sgt. Billy” would appear with them as a third banana for a while.  Eventually Sgt. Billy and Cactus Pete worked alternate weeks as Rex’s main sidekick.  Terrence became more involved in theatre and left the show to pursue a full-time acting career.  Sgt. Billy naturally stepped into the full-time role as Rex Trailer’s sidekick and would maintain that role right up until Rex’s death in 2013.


For more than 50 years, Sgt. Billy and Rex Trailer thrilled the hearts of baby boomers all across New England and throughout the world. For nearly 30 years they took thousands of kids and their families to California, Florida and other parts of the world with the Crimson Travel Tours.  Part of the job was to entertain for the huge crowds with Rex on guitar and Sgt. Billy on banjo.


They’ve performed throughout Southern California, Florida, Las Vegas and other cities around the globe.  Sgt. Billy has shared the stage with Jerry Lewis, The Lone Ranger, Clint Black, Irish Rovers, Tommy Makem from the Clancy Brothers, and he even got to jam with his idol, Pete Seeger in Pete’s home.


In the mid-90s, Rex and Sgt. Billy performed at the Foxboro stadium in front of an audience of over 50,000 people.  Sgt. Billy continues to perform throughout New England and Florida with fellow Boomtown alumni, Sam Donato and are both podcast members of the popular, Colonial Radio, featured HERE.


A true Renaissance man, Sgt. Billy is a licensed airline transport pilot and flight instructor and had a long career in aviation before founding his wealth management company.  He is married to the love of his life, Lennie, and they have two children and five grandchildren.