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The Inkspots were formed in 1934 from a group of porters working at the Paramount Theatre in New York City. The original band members were Jerry Daniels, Orville 'Hoppy' Jones, Ivory 'Deek' Watson, and Charlie Fuqua. After mediocre success, the group changed labels from 'Victor' to 'American Decca', and exchanging Jerry Daniels with vocalist Bill Kenny. They also changed their style from jazz/swing to slower more sentimental or romantic music. Bill Kenny would sing with his high tenor voice, and 'Hoppy' Jones would read choruses. This changed the group's popularity, and they were highly regarded in the forties.

The Inkspots first big hit was 'If I didn't Care', in 1939. Many more followed, and during the forties they had eleven Top Ten hits in the U.S. They changed their style very little during this time, because of fears of turning away public popularity.

'Hoppy' Jones died in 1944 and was replaced by Kenny's brother Herb, and shortly thereafter 'Deek' Watson was replaced by Billy Bowen. These changes did nothing to diminish their popularity, and they ended up featured in the films 'The Great American Broadcast' and 'Pardon My Sarong'.

More recently the Inkspots have been used for atmosphere in a couple of works. Their song "Maybe" was used in the opening sequence of the game Fallout (and a character in Fallout 2 sings the lyrics to it as well), while their song "If I Didn't Care" was in the beginning of The Shawshank Redemption.

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