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In August of, '2000', Denny appeared on Dick Clark's, "Your Big Break". A program that showcased the talents of people who naturally sound like different singers. Denny was chosen to sing Neil Diamond's "America" because of his uncanny similarity to Neil Diamond's unique baritone voice. The episode was the most viewed and was also the most re-run episode of the series.

This eventually lead to a chance meeting with Sean Kelly. A talented musician who was traveling with the group Sixpence None The Richer. A group most known for their hits, "Kiss Me" and "There She Goes". With Sean's help they created a group that has been playing in Nashville since, '2001'. "Denny Diamond and The Longfellows" has become a well known, long running act, performing a tribute to the music of Neil Diamond. They perform regularly in Nashville and are often headlining Festivals and Corporate events.

Denny can also be seen performing with his two son's Lucas and Spenser. Together they are known as "Denny Diamond and The Family Jewels". They have delighted audiences across the nation performing their fun and energetic tribute to one of America's favorite singer/songwriters, Neil Diamond. Mix in songs made famous by artists like Johnny Cash, Roger Miller and various other entertainers to round out an evening of great music. They have proven to be a great addition to any Festival or Corporate Event.