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Reynolds is most widely known as former lead guitarist and vocalist with the legendary Earth.Wind & Fire During that era, Reynolds also recorded with the group Chicago. His tenure with Earth, Wind & Fire lasted 14 years. Reynolds received an Image Award for lifetime achievement while a member of Earth, Wind & Fire. In the mid 90’s Reynolds was nominated for a Grammy for the popular song Sunday Morning, which Reynolds wrote and recorded with EWF.
In 2004, he formed Devoted Spirits with two former members of EWF, Morris Pleasure and original member Larry Dunn. They recorded and released a tribute CD to their former band called Devoted Spirits "A Tribute To Earth, Wind, and Fire". Sheldon also served as producer on a CD project for breakout vocalist Victoria White. The CD was released in May 2008 on the Kalimba label headed by his former mentor, Maurice White.