3. Hoboken is the birthplace of Frank Sinatra

Frank Sinatra Post Office

Frank Sinatra, born Francis Albert Sinatra, was born and raised in Hoboken at 415 Monroe Street. Sinatra was the oldest child of two Italian immigrants. He attended a number of Roman Catholic institutions around the city. Sinatra faced some health issues during his childhood, including severe scarring on his face that earned him the nickname “Scarface.” His mother was made a Democratic ward leader in Hoboken and notably chained herself to city hall in support of women’s suffrage. His parents ran a tavern during the Prohibition Era, during which time Sinatra learned to speak Yiddish and learn piano. He would sing on street corners around Hoboken and took a particular interest in big band music at his parents’ bar. His mother, though hesitant at first, saw great talent in Sinatra. By the time he enrolled at A. J. Demarest High School, he was arranging bands for school dances. He was ultimately expelled and ridiculed by his teachers for having no genuine talent or passion.

He took up as a delivery boy with the Jersey Observer, during which time he would perform at local bars and sing for free at radio stations. He would move to New York and begin lessons before taking up the role of singing waiter at The Rustic Cabin in Englewood Cliffs. Despite a major dispute between him and his girlfriend at the restaurant, this was where he got his first big break, a break that would make him the legendary singer and actor all New Yorkers know. He is memorialized in Hoboken with Frank Sinatra Boulevard and the Frank Sinatra Post Office, as well with as a giant statue near the waterfront.