Ermenegildo ‘Jilly’ Rizzo was an American restaurateur, entertainer and a long-time friend of Frank Sinatra.

Born in 1917 in the Hell’s Kitchen neighborhood of New York, Rizzo first worked for his father delivering ice to cafes and had a variety of other restaurant jobs before opening his eponymous saloon.

Jilly’s, located in midtown Manhattan, became known as the city’s swinging-est place to be. Sinatra frequented his old pal’s place often and brought along friends like the famous American bandleader and composer Count Basie.

As you can see from the menu, the food was standard stuff – people came for the atmosphere and the hope of bumping into America’s favorite crooner and his glamorous buddies.

Rizzo later became one of Sinatra’s chief aides and closest confidantes and was referenced in the song Mrs Robinson, featured in Sinatra’s 1969 album My Way. ‘And here’s to you, Mrs Robinson, Jilly loves you more than you will know…’

Rizzo was also a frequent guest on the comedy show Rowan and Martin’s Laugh-In, delivering one-liners in his monotone New York accent.

Sinatra, who was based in California, persuaded Jilly to open another establishment there in the late 1980s.

Rizzo died at the age of 75 in Rancho Mirage, CA, in 1992, when his car was struck by a drunk driver. According to reports at the time, Sinatra went into seclusion on news of the death of his old friend. He died in 1998.

This 1960s souvenir menu from Jilly’s in orange and cream stripes perfectly captures the fun and excitement of snagging a coveted table at Jilly’s in Manhattan. Sinatra even allowed his name to be used on the menu, which could be posted to friends.

Courtesy Private Collection.