Gerrilyn began singing at the age of 7.  After watching the movie "Porgy and Bess" with her parents, they gave her the album to listen to, and she played it and sang along with it daily for weeks on end.

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Gerrilyn received a B.A. in theater from Central Connecticut State University.  She performed in dinner theaters, regional theater and at the Connecticut Opera.  She toured Europe as the Crissy understudy and as a member of the Tribe in the musical "Hair" under the supervision of James Rado.  

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In 2013, she discovered cabaret by taking a class at the Singers Forum with Gretchen Reinhagen.  After performing in several group shows, she made her cabaret debut in 2019 with "Something Cool" at Don't Tell Mama directed by award-winning Gretchen Reinhagen with musical direction by David Gaines.  Gerrilyn was nominated for a 2019 BroadwayWorld Award for Best Debut Show, a 2020 MAC Award for Best Debut Show and a 2020 BroadwayWorld Award for Best Debut  Show - Run of Shows of the Decade.   

 

In 2022, Gerrilyn was nominated for a BroadwayWorld Award for Best Show for "If Joe Allen's Walls Could Sing & Other Hidden Gems" directed by Lennie Watts with musical direction by Steven Ray Watkins.

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In 2023, Gerrilyn was nominated for a MAC Award for Best Female Vocalist for "If Joe Allen's Walls Could Sing & Other Hidden Gems."