I’m not exactly sure when my fascination with Frank Sinatra and the Rat Pack started. I think it was around my Sophomore or Junior year of college, but I can’t pinpoint any specific experience that kicked it off. As you can see in the picture below I had that famous poster of the Rat Pack outside The Sands in my dorm room Junior and Senior year (on the wall next to the Clerks poster in the background). That’s also around the same time that I read Mr. S: My Life With Frank Sinatra by George Jacobs and William Stadeim. If memory serves, I read about the book in a magazine like People or Entertainment Weekly, thought it sounded interesting and somehow had the time to read it along with all the other assigned reading I had to do. See, Jacobs was Sinatra’s valet for about 15 years. Sinatra had been famous in the early 40s as a teen pop star. He rode that wave out to Hollywood where he starred in some movies, but the tides turned and he wasn’t on top anymore. In fact, he was on the bottom of the barrel. But in the early 50s, Mr. S was working hard to get back into the limelight with roles in some upcoming movies and a record that wound up selling big time. Around then he met Jacobs who was working for a big time agent and Frank basically stole him away. From there Jacobs was living the high life meeting pretty much every famous person in the world including some up and comer by the name of John F. Kennedy. Jabobs was with Frank through lots of good times and then things started on a decline once Sinatra married Mia Farrow (I had no idea this happened before I read the book because it lasted for such a short period of time). Jacobs was out one night while the Mia/Frank relationship was nearly over, she happened to come into the same club he was killing time in, she asked him to dance, he agreed, some paparazzi snapped a picture and the next day, Jacobs was completely cut off from the man he served so well all those years without even a “kick rocks kid.”

Mr. S is Jacobs’ account of those 15 years. He kicks the book off at the end, explaining what happened leading up to his firing–or more accurately shunning–by Sinatra. The book however is not a bitter recounting of good times from a man on the down and out. Jacobs seemed to be living well when the book was published in 2004, though for the life of me I can’t find any recent information about the man online, he doesn’t even have a Wiki page which is mind boggling. The author offers what seems like a very fair and accurate account of Ol’ Blue Eyes as well as plenty of other legendary names in Hollywood and even politics. If you’ve ever had an interest in the history of Hollywood and what people were really like, this is a great book to read. I know you’re supposed to always question the narrator, but I believe what Jacobs says because he says as much about himself as anyone else. It really opened my eyes to the Kennedys who come off as a bunch of fun-loving rich kids whose dad bought them into power and helped sway the public by appealing to Sinatra’s desire to be respected by important people and to be important himself. It might sound crazy, but Frank Sinatra and the Rat Pack actually had a pretty big hand in getting JFK elected.

The portrait that Jacobs paints of Sinatra is one of a man who didn’t only love vice, but people as well. He had many a lover, both common and celebs like Marilyn Monroe, and even more prostitutes, but Jacobs also says he had a great respect for working girls and treated most of his women very well. Sinatra also helped a lot of people he met–mostly women–by giving them money or helping to pay for their kids’ school. He was a sucker for a sob story apparently. Mr. S was a hard drinking, hard working man who wanted to prove everyone in Hollywood wrong when they counted him out. He sought the attention of more famous and established people, but would cut someone off after the slightest transgression. On a movie set he would only do one take because his acting hero Boris Karloff said that’s the way to go. He was coarse, but friendly, feeling for anyone who was looked down on by society, thinking of himself as in the same boat thanks to his Italian upbringing in Hoboken New Jersey. By today’s standards he’d be called insensitive and insecure, but at his height he was king of the world, living the kind of life that lots of people dream about living.

A book like this is interesting because it gives a lot more context to the life of a legend. He isn’t JUST a dude who could sing, act and drink Jack Daniels with the best of them. Frank Sinatra was a regular person with the same flaws many of us have. You come away feeling a little bad for Sinatra as things started to crumble around him towards the end of Jacobs’ tenure with him. That cool guy 50s mentality was starting to give way to the swinging 60s, a culture the then-50 year old crooner could hardly stand. Jacobs and Stadiem do a fantastic job of creating a roller coaster ride effect with the book, starting with the tragic ending which makes you think Mr. S is kind of a dick, then going back to the beginning of the story when he was down and out, building him up to a hero of sorts and then reminding you that he was a jerk. But it doesn’t end completely on a down note as far as Jacobs is concerned, though it is sad that he and Sinatra never reconciled possibly because Sinatra’s wife Barbara seemed to have a real dislike for Jacobs, going so far as to not even invite him to Frank’s funeral when he passed away in 1998 at age 82.

Even with all the warts revealed in the book, there’s still a lot to respect about Sinatra. Yes he was insecure and had a pretty big weakness for the ladies, but he was also a good man who liked to help people and, to spill the same ink a million people already have, he did things his way and he did them well. If you have any interest in Sinatra, the Rat Pack, Hollywood, Las Vegas (another place Sinatra helped keep alive) and just the overall culture shift that happened between the 50s and 60s, Mr. S is the perfect book to read.