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.
Although Craig took guitar lessons during his childhood, it wasn't until his young adult years that he began, in earnest, to improve his skills. While serving in the United States Navy, he played in several country-western bands on the various military bases in Okinawa, Japan. During his tour of duty overseas, Craig nearly lost his life in a car accident. This led to a medical discharge and the opportunity to attend the Musician's Institute's (Guitar Institute of Technology) in 1983. After graduating, he continued his musical education at West Los Angeles College.
In 1983, Craig met and fell in love with his future wife, the gifted, professional musician, Cali Rose and they performed briefly as a duo in the early 1980's at various clubs in the Los Angeles area. However, Craig eventually decided to branch out on his own. Finding himself out-of-sync with 1980s rock music, he decided to draw upon his acoustic-folk and country-western roots and joined "American Dreamer," a country-rock band that played various venues, including the Palomino Club, in North Hollywood.
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. [see more on Howard] 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 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."