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Craig began playing the guitar at the age of nine, in Long Beach, California, where his eclectic tastes were fashioned by the folk, rock, soul, jazz and popular music of the 1960s. Some of his earliest memories include listening to the Bossa Nova classics of Antonio Carlos Jobim on his parent's stereo along with Nat King Cole, Frank Sinatra and Ella Fitzgerald, to name a few. Like many others of his generation "The Beatles" had a profound effect upon Craig's musical sensibilities. He became fascinated by the arrangements of Beatles songs by José Feliciano, Laurindo Almeida and Chet Atkins.
After years of struggling in Los Angeles as a musician, Craig decided to make a major change in his life. In 1991, he returned to college and earned BA and MA degrees in History from UCLA. During this time, he had the good fortune to meet the legendary arranger, Howard Heitmeyer. Within moments of their first meeting, Craig realized that he'd met his teacher. "It was a truly profound moment in my life. I realized I'd met the person who could teach me how to play the way I'd always wanted to be able to play."
In 1994, Craig and his wife Cali made their first trip to Hawaii. While on the plane, Craig read an article on the legendary jazz ukulele player, Lyle Ritz and eventually heard some of artist's recordings. He was mesmerized by Ritz's jazzy chord melodies. This seed eventually came to flower in 2004 when Craig purchased his first ukulele: A tenor Fluke from Flea Market Music. A few months later, Craig asked Howard if he'd create chord melody arrangements for the tenor ukulele. Fortunately, Howard agreed and they continue working together to this day. Many of Howard's arrangements can be heard on Craig's CD, "Tenderly," along with the master himself playing his original song, "Craig's Waltz."