The Unique Restaurant Job Frank Sinatra Had Before Becoming Famous

Frank Sinatra may be a household name even over a century after his birth, but he had to start somewhere. Most celebrities had humble early jobs, and Sinatra was no exception, with one of his first taking place in a restaurant. While he had a reputation for his famous spaghetti-and-meatballs recipe, this job wasn't in the kitchen. Instead, Ol' Blue Eyes had a brief stint as a waiter at the Rustic Cabin in Englewood Cliffs, New Jersey.

But wait, you don't know the best part yet! Sinatra was not just a waiter, but a singing waiter. While this likely isn't a huge shock, the notion of a musical waiter isn't something you come across nowadays. In the 1930s, singing waiters were a bit of a novelty, and Sinatra thrived in the role. He was said to croon and do a bit of comedy at tables, and served as master of ceremonies when the restaurant acted as a nightclub for dancing in the evenings. 

It was actually a step backward for Sinatra, as he'd previously been in a singing group as a teen called the Hoboken Four, but that chapter in his professional career didn't last long. By all accounts, he hated the restaurant, but was good at the job and understood that it afforded him the opportunity to sing with visiting acts. While he couldn't stomach garlic in most dishes, Sinatra was an outspoken patron of many Italian restaurants after his stint. However, he barely breathed a word about Rustic Cabin, except to say that he couldn't wait to move on.

Some people think of Frank Sinatra as a high-class man, but he often preferred the simple things. Even the last thing Sinatra ate was a simple grilled cheese sandwich. With this in mind, it's no surprise that he'd thrive as a waiter, especially a singing one. It was his raw talent that caught the eye of Harry James, a big name in music at the time. In exchange for his work at the restaurant as head waiter, sweep-up man, and chief bottler, Sinatra was given airtime on the venue's radio broadcast. While entertaining audiences in person, his voice also graced the airwaves, and it was his singing on the radio that enticed James to visit Rustic Cabin. 

Sinatra was waiting tables that night, but he removed his apron and got up on stage when he saw James in the audience. He sang "Night and Day," and James immediately knew that he'd found something special. Sinatra auditioned to be part of James' band and became a vocalist in June of 1939. Unlike with his restaurant job, he spoke well of James over the years and credited this band as his actual start. Although he'd join Tommy Dorsey only six months later, this was the stepping stone Frankie needed to launch himself into international stardom. 

Sinatra went on to win three Oscars, numerous Grammys, and even the Presidential Medal of Freedom. His songs and movies are still known around the world to this day, and it all started because of a singing waiter job. While Rustic Cabin is long gone, as it closed and burned down some time ago, you can still visit Sinatra's favorite New York bakery, which serves up some of his preferred pastries.