- His Father Aldo DeMeo was a Bailiff in Broward County Florida when Dustin Hoffman and Company came to town to film "Lenny". He was offered the opportunity to play the Bailiff in "Lenny", which he accepted. During the Acadamy Awards Show in 1974 when "Lenny" was Nominated for "Best Picture", the scene where Dustin Hoffman is dragged out of the Courtroom by Aldo DeMeo the Bailiff was chosen as the clip shown to represent the movie.
- Has been best friends with Actor Kent Lane for over 35 years.
- As of October 2016, Jessie Eastland has released 12 of his original tunes on the Amy Deb label. Some of the tunes are fully orchestrated, and some Jessie plays all the instruments. These songs are available for download on all online outlets.
- Is the son of Actor Aldo DeMeo.
- Changed his name to Eastland in 1982, to reflect on "the land in the east" where he was born and raised.
- Jessie Eastland has never been married.
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