Holly was born Haraldo Santiago Franceschi Rodriguez Danhakl in Juana Diaz, Puerto Rico. The product of a short-lived marriage between his mother, Aminta, a Puerto Rican, and an American soldier of German descent stationed in Puerto Rico, who met Haraldo's mother on leave, got her pregnant, married her, then quickly departed.

Although his mother Aminta married Joseph Ajzenberg when Harold was only five years of age, he wasn't legally adopted as by his step-father until the age of fifteen, changing his last name to Ajzenberg.

Haraldo was raised in a household that included 8 aunts, 1 uncle, 5 cousins, 2 grandparents, 6 chickens and 3 pigs. He later changed her first name to Holly after Holly Golightly in Truman Capote's story Breakfast at Tiffany's.

Holly made his/her night club debut in 1973 at New York "Reno Sweeney's" on a double bill with Betty Rhodes. He then acted in Warhol's film Trash. Holly was hired by the producers of Tootsie (1982) to coach actor Dustin Hoffman in his role as 'Michael Dorsey/Dorothy Michaels' in the art of being a man acting as a woman in films.

The legendary Lou Reed, Velvet Underground song Take a Walk on the Wild Side refers to Holly Woodlawn, indelibly imprinting her story in American pop culture. "Holly Came From Miami, F-L-A..." are the beginning lyrics forever describing Holly's arrival in New York City, and ultimate imprint on the landscape of 1970s chique.

Holly also appeared in Allan Mindel's film, Milwaukee, Minnesota (2003), with Randy Quaid, Bruce Dern and Josh Brolin. Hee was also interviewed extensively in Craig Highberger's documentary on Jackie Curtis, Superstar in a Housedress (2004).

Holly currently resides in Los Angeles. In January 2004, he was admitted to intensive care after complications from an operation on his arm and shoulder which he broke during a fall.

Holly is currently planning a film based on his/her autobiography, The Holly Woodlawn Story: A Low Life in High Heels.