By the age of three, Shearing learned to play the piano. Then, Linden Lodge School for the Blind was his home away from home for four years. While in school, Shearing also learned to play the accordion. He even performed at a local pub for the equivalent of almost 5 dollars per week.



Shortly after, Shearing joined a band of blind musicians. In 1937, at the age of 18, George Shearing began recording music with Leonard Feather. After three years of recording with Feather, Harry Parry's band took in Shearing. During this time, Shearing was also honored as the winner of seven Melody Maker polls.

Although he moved to the United States in 1947, he became a United States citizen in 1956. During those nine years, George Shearing began playing a new style of music that incorporated swing, bop, and modern classic.

1949 marked the year that Shearing founded the first George Shearing Quintet. The quintet included Marjorie Hyams, Chuck Wayne, John Levy, and Denzil Best. The first single from the quintet was September in the Rain, and it sold over 900,000 copies. In 1969, the quintet stopped recording with Capitol; however, Sheaving solved the problem by starting Sheba, his own recording label.

From 1970 to 1978, the quintet disassembled. During these eight years, The Reunion and With George Shearing were released. Shearing recorded and released these albums in collaboration with well-known bassist Andy Simpkins, drummer Rusty Jones, and musician Stephane Grappelli. Over the years, other collaborations included music with Montgomery Brothers, Marian McPartland, Brian Q. Torff, Jim Hall, Hank Jones, Kenny Davern, Nat King Cole, Peggy Lee, Ernestine Anderson, Dakota Staton, Carmen McRae, and Nancy Wilson. Concord Records signed George Shearing in 1979. Under Concord Records, he won Grammy awards in 1982 and 1983.

From the 1980's through the 1990's, George Shearing performed at numerous festivals, was on numerous radio shows, and made many recordings. Collaboration with Neil Swainson occurred in the 1990's through the early 21st century. The Rare Delight of You, an album with Shearing and The John Pizzarelli Trio, was released in 2002. It received great reviews.

Along the way, a now-popular piano technique was named after Shearing. It is called Shearing Voicing. This technique uses a block chord with the melody on top in the right hand while the left hand repeats the melody in a lower octave and makes it stand out over the right hand. It is a difficult style to perfect, particularly when playing solo. In his quintet Shearing has the vibes player playing the melody also, creating what some have described as a "shimmering overtone" effect.

Jack Kerouac's novel On the Road describes a lovely Shearing performance. In all of his years of musical service, Shearing recorded and released close to 100 albums and has received many notable awards. Westminster College in Utah gave him an honorary Doctor of Music degree in 1975. Shearing also earned the Horatio Alger Award for Distinguished Americans in 1978. In 1993, the Ivor Novello Award for Lifetime Achievement was given to him. Shearing received another honorary degree from Hamilton College in New York. It was also a Doctor of Music honorary degree. He received the first American Music Award by the National Arts Club of New York in 1998. Recently, the BBC Jazz Awards' Lifetime Achievement Award was given to Shearing in 2003. George Shearing became Sir George Shearing in 2007 when he was knighted for his services in music.

Now, Sir George and his wife travel from their New York apartment to Berkshires frequently. Shearing is semi-retired.