In the late ‘50s and throughout the ‘60s, Henry Grimes played acoustic bass with many master jazz musicians of that era, including Albert Ayler, Don Cherry, Benny Goodman, Coleman Hawkins, Roy Haynes, Steve Lacy, Charles Mingus, Gerry Mulligan, Sunny Murray, Sonny Rollins, Pharoah Sanders, Archie Shepp, Cecil Taylor, and McCoy Tyner. Sadly, a trip to the West Coast to work with Al Jarreau and Jon Hendricks went awry, leaving Henry in downtown Los Angeles at the end of the '60s with a broken bass he couldn't pay to repair, so he sold it for a small sum and faded away from the music world. Without a bass, a vehicle, or a telephone, he was truly lost. He survived by doing manual labor and redirecting his creative powers into writing poetry.

He was discovered there by a Georgia fan in 2002 and was given a bass by William Parker, and after only a few weeks of ferocious woodshedding, Henry emerged from his little room to begin playing concerts around Los Angeles, and made a triumphant return to New York City in 2003 to play in the Vision Festival. Since then, Henry has played nearly 600 concerts (including many festivals), touring in 30 countries throughout the U.S., Canada, Europe, the Middle East, and Asia, playing and recording with many of this era's music heroes, such as Rashied Ali, Marshall Allen, Fred Anderson, Marilyn Crispell, Andrew Cyrille, Bill Dixon, Edward "Kidd" Jordan, Roscoe Mitchell, David Murray, William Parker, Marc Ribot, Wadada Leo Smith, and again, Cecil Taylor. Henry made his professional debut on a second instrument (the violin) at Lincoln Center alongside Cecil Taylor at the age of 70, has seen the publication of the first volume of his poetry, "Signs Along the Road," and creates illustrations to accompany his new recordings and publications. He has received many honors in recent years, including four Meet the Composer grants.