The search for more opportunities, experience, and advanced music education led the young bassist to journey from The Midlands to work in London in 1964, where he began to study with James Edward Merrett, the principal bassist with the London Philharmonic. A year later, Merrett recommended him for a scholarship to the Guildhall School of Music and Drama and Holland was on his way.
The mid-‘60s were an exciting time to be in “Swinging” London: the U.K. was pulling itself free from an extended postwar, economic decline and a whirlwind of fresh, cultural ideas (especially musical) was in the air. Holland was soon exploring more advanced classical and avant-garde music, as well as the work of jazz bass masters from Ray Brown, Leroy Vinegar and Charles Mingus, to Scott LaFaro, Jimmy Garrison, Ron Carter and Gary Peacock. He began to perform regularly with bands fronted by leaders at the cutting edge of the U.K. jazz scene: Tubby Hayes, Ronnie Scott, Chris McGregor, Evan Parker, and John Surman.
Holland was a mere 19 years old when he began to appear at Ronnie Scott’s jazz club in London’s Soho district, supporting touring jazz veterans like Ben Webster, Coleman Hawkins and Joe Henderson. That was the venue in which famed trumpeter Miles Davis—who was about to transition from purely acoustic music to more electric instrumentation in 1968, including rock and funk influences—first heard Holland. Davis asked him to take over the bass chair in his band at a time when generations of musicians and music fans were intensely focused on every step the trumpeter was taking.
Joining Davis’s groundbreaking, semi-electric band was the catapult that launched Holland’s career to the international stage. As the world watched and listened, he contributed to albums that pointed the way to the future—Filles De Kilimanjaro, In A Silent Way, Bitches Brew—and performed in jazz clubs and rock festivals, helping to lay the groundwork for the rise of Fusion jazz, an important member of a brotherhood of innovators adept at older and newer jazz vocabularies. While still with Davis, Holland gigged and recorded with other musicians as well, including the Thad Jones/Mel Lewis Orchestra, Chick Corea, and Joe Henderson.