Rosa “Rambling Rose” Pryor, a native Baltimorean, graduated from Edmondson High School in 1963 and attended Community College of Baltimore and Morgan State University to study business and law.
Rosa has been an R&B music enthusiast since 1957. She started as a singer, songwriter and musician, playing saxophone and piano for the group she founded, “Little Johnny and the Twilight’s”. While performing as the group’s lead vocalist she wrote, produced, and recorded a tune called, “Thanks Mr. D.J.” on Decade Records under the management of the late Paul “Fat Daddy” Johnson, and Rockin’ Robin, two of the greatest radio personalities in our time. The song was Rosa’s and her group’s tributes to them for helping her get started in the music field. On tour, Rosa and The Twilight’s had an opportunity to meet and open for great performers such as The Shirelles, The Chantels, Ruby & the Romantics, Jimi Hendrix, and Sam Cooke. Her commitment to every aspect of the music industry is a testimony of her deep soul felt love for artistry in its entirety.
As an entrepreneur since 1964, Rosa has helped hundreds of musicians establish their careers. She gathered local neighborhood children from their nests, pruned and greased their musical wings, and sent them soaring into flight. Rosa recognized that these junior and senior high school students needed only her love, expertise, and guidance to tone their vocal and instrumental talents. Her passions nourished more than twenty music groups. She coordinated, trained, counseled, and managed them individually and as a group. With the help of her dear friends in radio business such as Kelson ‘Chop Chop’ Fisher, Al Jefferson, Dell Edwards, Rockin’ Robin, Fat Daddy, Bob Dockins, Larry Dean, Sir Johnny O and the renowned ‘Hoppy’ Adams, she was able to book her bands all over the east coast. Hoppy Adams became her Master of Ceremony for the shows she booked on the Eastern Shore area for many years.
In 1967 Ms Pryor acquired her legal Entertainment License to book national and international entertainers out of state and large venues. Starting in 1967, she owned, managed, assisted and produced many professional, local R&B, Pop and Jazz musicians and singers including The Vandals, The Fabulous Friends, The Jewel Box Review, First Class, The Softones, Julius Brockington Trio, Bobby Starr, Winfield Parker, Benny Johnson, Lady Rebecca, Nikki Cooper, Mickey Fields, Andy Ennis, Sir Thomas Hurley, Carlos Johnson, Bobby Ward, Tiny Tim Harris, Clayton McLendon and Dennis Chambers, just to name a very few. Among the national and international acts that have benefited from Rosa’s promotional skills were entertainers such as Sir Walter Jackson, Joe Tex, Sonny Til and the Orioles, The Clovers, Richard “Groove” Holmes, Harold Melvin and The Blue Notes, The Drifters, The Swallows, Phillipe Wynn, Wild Man Steve, Millie Jackson, Stanley Turrentine, Jimmy McGriff, Peg Leg Bates and Jack McDuff just to name a few.
Because of her unyielding passion and diligent efforts, Rosa soon became known as one of the top Black female promoters and managers in the state of Maryland, the metropolitan area, and the east coast. Later she co-promoted with giant promoters in the business such as the late Elzie Street and Nick Mosby also, Biddy Wood, Rufus Mitchell, and Lou Karpouzie. As a professional, licensed booking agent she established her own promotional/marketing agency called Rosa Pryor Productions, which booked many of the jazz musicians in the Baltimore/Washington area. She proved an invaluable asset to local nightclubs and bar owners as an Entertainment Business Developer and Consultant. She was the manager of the famous Club Casino on Baltimore’s Pennsylvania Avenue, under the ownership of Little Willie Adams; and General manager and booking agent for the Elgin Lounge under the ownership of the late Ambrose Robinson; The Point After Night Club when it changed hands to Bob Matthews, also hired her as his club promoter & manager were Lydell Mitchell when the club changed name and was called the Hollywood Palace. In the early years, Rosa joined one of the famous top Black van clubs in Maryland, called the Nomads Van Club, being the first and only female to be a member in the early ’70s. During the mid-1970’s Rosa started the Baltimore historical Van Club’s & CBer’s (Citizens Band Operators) Breakfast Shows and “Coffee Breaks” at Pat’s Lounge on Saratoga Street in Baltimore and later promoted this event to other clubs in Baltimore. As a Ham Operator, she had CBer’s coming from all over the Baltimore/Washington Metropolitan area and other states to join her.
In 1971, the late, Ida Peters, the Afro-American Newspaper Entertainment Editor quoted Rosa as being, “…the most talked about, most popular and the only Black female promoter & licensed Booking Agent in the state of Maryland/Washington Metropolitan area ….”.
Pryor has booked and promoted entertainment all over Maryland and the East & West Coast including Baltimore, Eastern Shore, Cambridge, and Waldorf. She has also booked her talents to Washington, D.C., New York, New Jersey, Delaware, California, Pennsylvania; North & South Carolina, Detroit, and Chicago, etc. She has co-produced shows and concerts at Painter’s Mill Music Fair, Baltimore Civic Center, Capital Center, Carr’s Beach, Ft. Smallwood and Ebbs Picnic Grove in Baltimore, Maryland.
Rosa’s trade name is “Rambling Rose”, a name that was given to her by the late great Nat ‘King’ Cole when she was touring in the late ’50s as his opening act. The color red has always been her favorite color and when she used to perform, she always dressed in red exotic, sexy gowns and gave out her favorite flower, a long stem red rose, which became her signature. During this time, Rosa was not only a singer, but a musician, playing piano and saxophone; she was a recording artist, record producer and song writer.
Rosa ‘Rambling Rose’ Pryor is the Entertainment Editor and Entertainment Columnist for the Baltimore Times and the Annapolis Times from 1997 to 1998. She continues to write her column today for the Baltimore Times, 40 years later. Rosa wrote an entertainment column for the “Buzz N’ Around Baltimore Magazine” and traveled the country and the Caribbean Islands covering all the jazz, blues, and gospel at music festivals. Rosa is the author of a collector’s item book called, “African-American Entertainment in Baltimore”, which was published in June 2003 and sold out the first print in six weeks and now the book is in its third print. She began her research to write this book on the legendary Pennsylvania Avenue clubs and entertainment of its heydays in 1989. Her second book, which is also a collector’s item, is called “African-American Community, History, & Entertainment in Maryland” which she published in 2013. Both books are in the Library of Congress. Her third book, published in 2023, called “Baltimore and Maryland Black History Stories, Who? What? When? and Where?; 1950s-1980s”.
Rambling Rose, as her readers affectionately call her, is formerly the entertainment columnist and reporter with the Afro-American Newspaper and has been since 1998 until 2020; The Informer Newspaper 1996-1997, The Northwest Voice from 1997-1999 and she freelance for other periodicals and have over 400,000 readerships. She is the Entertainment journalist, Entertainment Reporter and Columnists for the Baltimore Times Newspaper for the past 40 years until present. Rosa is a long-time member of the National Association of Black Journalist, (NABJ).
Rosa was the Founder, CEO, and Chairman of the Board of the Rosa Pryor Music Scholarship Fund, Inc. created in 1991-present. The fund provides money for gifted and talented children aspiring musicians, ages 5-17 years old, to help pay for tuition, voice and music lessons and purchase instruments. Her organization is the only one of its kind in the country. Throughout these years she has provided over 400 children scholarship successfully and has honored over 100 local veteran musicians. She is also the Co-founder & CEO of an entertainment company with her husband, William ‘Shorty’ Trusty, called “RoseGarden Entertainment Enterprises, Inc.”. This is a company that provides entertainment, local and national for clubs, casinos, hotels, social events, and racetracks, (but not active currently).
She is a proud Sister of the Trinity Chapter No. 5, Order of the Eastern Star, Prince Hall Grand Lodge, and Affiliation since 1989. She is also Past Daughter of the Elks of Zorah Elliott Temple #717 of Baltimore, Maryland.
Rosa is a Honorary Member of Left Bank Jazz Society, Inc.; Honorary Member M.U.L.B.A. (Maryland United Licensee Beverage Association), was a Board Member of Jazz Expressways Foundation and a proud civilian member of the Vanguard Justice Society. She was recently honored by Wilber Fletcher of WLF Entertainment Productions; some Motown Recording Artists and her Peers celebrating 65 years in the Entertainment Arena.
She has received numerous awards since the 1970’s from organizations, television stations, radio stations, governors, mayors, congressmen, senators, councilmen, delegates and other elected officials, dignitaries, and renowned organizations.
In 2001, Rosa became Mrs. William (‘Shorty’) Trusty, but her lifetime friend for over 63 years. They are partners in Business and soul mates! She is the mother of 4 and grandmother of 22 and great-grandmother of 27.
Rosa Pryor-Trusty, affectionally known, as ‘Rambling Rose’ and always ends her documents saying, “I’m Musically Yours”!
Bio and photos courtesy of Rosa Pryor-Trusty.
