The Chestnuts, sometimes called The Five Chestnuts, were not the typical New Haven doo-wop group. Unlike the others, this group had a female lead singer, Ruby Whitaker. However, she wasn't the original singer. The original lineup (before multiple lineup changes Leroy Griffin (lead, but not the Leroy Griffin, lead singer of The Nutmegs), Lymon Hopkins (first tenor ), Frank Hopkins (second tenor), Jimmy Curtis (baritone), and Reuben White (bass). With the help of record producer and company owner Joe Davis, this lineup of The Chestnuts recorded their first single on Davis Records, "It's You I Love" with the b-side being "Love is True" in 1956. Even with "It's You I Love" being played on major stations in New York City and Philadelphia, it didn't make the national charts.

The Chestnuts eventually got dropped by Davis Records and switched to Standards Records out of New Haven in 1957. Here, the group recorded several more singles before switching labels yet again to Elgin and Drum Records in 1959. Whitaker also left the group the same year and was replaced by Bill Baker, who had experience recording with The Five Satins. This new lineup recorded a couple of more singles but did not do any damage on local or national charts. The band eventually broke up around this time.

"Forever I Vow"

"It's You I Love"