Born Jessie Robert Demeo in Brooklyn NY, and raised in the Rosedale Queens area to Aldo and Amelia Demeo. Moved to Florida in 1969 with entire family. Attended Broward Community College for two years while Playing in popular So. Florida rock band Latifundia. Finished college at University of Michigan in 1972. Changed his name to Jessie Eastland when he arrived in Los Angeles in 1982, and became a Glamour Photographer.

While still in Florida, he was taking live action stills for the movie Sometimes Aunt Martha Does Dreadful Things (1971), when the director asked him if he wanted to play a main character in the film. Jessie agreed, and that was his only acting credit in the industry.

He went on to do live action stills in Hollywood, as well as expanding his Glamour Photography. Today, Jessie Eastland is a nature photographer for Wikipedia, and Skytrek.life. He also continues to write, record and release his music.

As of this writing (2021) Jessie resides in Joshua Tree, California, and spends most of his time shooting the sky for his website: Skytrek.life