[2] He took up the violin at the age of 12, and then began playing tuba, English horn, percussion, finally switching to the double bass at Mastbaum Technical High School.

[4] Gradually growing interested in the burgeoning free jazz movement, Grimes performed with most of the music's important names, including pianist Cecil Taylor, trumpeter Don Cherry, saxophonists Steve Lacy, Pharoah Sanders, Archie Shepp, and Albert Ayler.

In 2002, he found Grimes alive but nearly destitute, without a bass to play, renting a tiny apartment in Los Angeles, California, writing poetry and doing odd jobs to support himself.

Bassist William Parker donated a bass[6] (nicknamed "Olive Oil" for its distinctive greenish color) and with David Gage's help had it shipped from New York to Los Angeles, and others assisted with travel expenses and arranging performances.

Following his return in 2003, Grimes played at many venues around New York City and on tour in the United States, Canada, and 30 countries in Europe, the Far East, and Brazil, often working as a leader, making music with Rashied Ali, Marshall Allen, Fred Anderson, Marilyn Crispell, Ted Curson, Andrew Cyrille, Bill Dixon, Dave Douglas, Andrew Lamb, Joe Lovano, Roscoe Mitchell, William Parker, High Priest (from Anti-Pop Consortium), Wadada Leo Smith, Cecil Taylor (with whom Grimes resumed playing in October, 2006 after 40 years), John Tchicai, and many others.

Grimes played with Ben Morea, accompanying simultaneous slide and film projections by Aldo Tambellini and sound recordings of the late Calvin Hernton's radical poetry.

On June 7, 2016, he received a Lifetime Achievement Award from Arts for Art/Vision Festival on opening day at Judson Memorial Church in New York City.

[9] with Mose Allison with Albert Ayler With Bill Barron with Roy Burns with Don Cherry with Walt Dickerson with Shafi Hadi with Roy Haynes with Lee Konitz with Rolf Kühn with Carmen Leggio With Gerry Mulligan with William Parker with Marc Ribot with Sonny Rollins with Pharoah Sanders with Shirley Scott with Archie Shepp with Billy Taylor with Cecil Taylor with Lennie Tristano with McCoy Tyner with Marzette Watts with Frank Wright Additional recent CD releases can be found at |url=https://henrygrimes.com/store Archived 2020-06-11 at the Wayback Machine].