Osgood first encountered the piano at age six. He recalls: "I used to hang around an old man in my community named Mot Willis, who was featured on several High Tone Records compilations. He is also listed in the Afro-American folkloric song book along with Scott Dunbar, K.C. Duglas, Fidlin' Joe Martin, Fred McDowell, Sam Chatman, Shirley Griffith and Mager Johnson to name a few. Mister Mot used to sit on the front porch steps of his home every evening and play his acoustic guitar. I couldn't help hanging around him all the time because I loved to hear him play. Coming from a poor family, I was glad to get that toy "charlie brown piano" that I got for Christmas, and I would run home afterward to play the tunes I heard
Mot Willis play." Osgood has entertained audiences around the world since 1982, touring with the island group Purple Haze and experiencing the musical cultures of Thailand, Filipines, Tokyo and Taiwan.

Osgood writes, records and performs his own music. He is noted for his energetic musical performances which may include dramatizations, skits and educational dialogue about the music he loves, his relationships at work and in the community. Osgood's style is melodiously soothing, even in an acoustic setting, creating a panarama of multi-layered synthesis seldom seen or heard throughout the entire world. Though traveling extensively throughout the United States, Osgood has found much contentment performing in and around Jackson, Mississippi's Malaco Records.

In 2003, Greg Osgood was joined by a female vocalist from Mississippi, Cee Blaque. Together, they comprise Osgood & Blaque Duo-Band! As a solo performer for many years, Osgood has followed the digital age carefully, finding innovative ways to keep up with the contemporary music scene, even forging his compact duo-band onto the battlefield of big-band stages and venues. Blaque admits: "When we found ourselves on stage opening for known bands that had six or more members, I knew that we were considered a good duo act. But, it was when our duo-band was perferred over a popular six-piece band, that we realized things were changing".

Blaque's vocal delivery and careful harmonic phrases are a deep personification of her heartfelt yearnings while growing up in and around the Mississippi Delta and Catfish Row. Blaque's harmonica style has been compared to that of Louisiana born, Little Walter, who achieved a horn-like sound on his harmonica, that “expressed his highly imaginative improvisations reminiscent of the bop jazz saxophonists of his day“.-Bill Dahl, All Music Guide When Blaque joined Osgood in 2003, her words were an emphatic: "I don't want to sound like every other harmonica player on the block". "Well, its been a long time since Little Walter has been on our block!", Osgood says.