The movies and TV you need to watch, the music you need to hear, the books and comics you need to read, the games you need to play — The Playboy Library is an ongoing series that offers the 21st century man the pop ammunition to carry himself as a gentleman of culture. Never obvious, always essential.

If you want to hear Francis Albert Sinatra in finest voice you want to listen to September of My Years. If you want to hear him lament over love and loss in what many consider to be the first ever concept album you want to listen to In the Wee Small Hours.

However, if you want to experience the miracle of time travel; journey to Sin City when it truly was Sin City; get blown out of your seat by a 17-piece band led by a jazz legend and fronted by a performer every man in the room wanted to be and every woman wanted to be with — well then, you want to listen to Sinatra at the Sands.

Live albums are always a mixed bag. At best they give you a marginal idea of what an artist is like live; at worst they are nothing more than poorly performed, poorly recorded greatest hits. Thankfully, Sinatra at the Sands falls into neither of those categories. Led Zeppelin’s The Song Remains The Same, Cheap Trick’s Live At Budokan, The Band’s Last Waltz — all great live records documenting great live concerts. But Sinatra didn’t perform “concerts.” Sinatra was an entertainer. You dressed sharp, took your best girl by the arm and blew your week’s paycheck in one unforgettable night: an overture, songs, stories, a monologue and some soft shoe.

Sinatra put on a show.

So where better to record his first commercially released live album than the Rat Pack’s own “Fortress of Solitude,” the Sands Hotel’s Copa Room, the prime filming location for Ocean’s 11. In early ‘66 Sinatra stepped on stage — backed by Count Basie and his Orchestra performing fresh arrangements by an up-and-coming wunderkind named Quincy Jones— and completely hypnotized an audience with what is now considered the seminal performance of his career.

By 1966, Sinatra’s tenure as a teen idol and crooner were well behind him. This is the birth of The Chairman of the Board — a man and performer who has paid his dues and is deserving of respect. From the moment he saunters on stage and mutters the rhetorical, “How did all these people get in my room?” one thing is abundantly clear: This is a seasoned pro in his element. Rock bands play a show. Sinatra is working the room. For the next hour he gives you the distinct feeling you’ve already downed your first scotch of the evening and have a nice, little buzz going.

The set list is a virtual guided tour of the Great American songbook: “Come Fly With Me,” “I’ve Got A Crush On You” and “I’ve Got You Under My Skin” — the gold standards that would close most singers’ sets are merely warm-ups for Frank.

Having previously worked together on 1962’s Sinatra-Basie and 1964’s It Might As Well Be Swing, the chemistry between the singer and bandleader is the album’s true secret weapon and nowhere is their friendship more evident than at the top of “Fly Me To The Moon (In Other Words)”, where Sinatra, after a shaky start, pleads with the Count, “Now this man here is going to take me by the hand and lead me down the right path to righteousness…in the right tempo.” They screw it up anyway and laugh it off, never missing a beat.

This time capsule requests one thing of you to completely surrender to it — you must put it in context. Sundays still belonged to Ed Sullivan. Martin Luther King Jr. and Robert Kennedy were still alive. Men wore suits on airplanes and had yet to set foot on the moon. With dated references to comedian Joe E. Lewis, and close friend/restaurateur Jilly Rizzo, the monologue (otherwise known as the “Tea Break” section of the act) has not aged well — nor have the unfortunate Amos & Andy impressions — but the attitude still remains and with it, the feeling that, if only for one night, you were cool enough to hang with the Rat Pack.

So pour yourself a single-malt, close your eyes and immerse yourself in Sinatra at the Sands. It is the closest you will ever get to experiencing one of the greatest performers that ever lived, at the height of his powers, backed by the hottest band on the planet, playing the best room at the best Casino during Las Vegas’ glory days.

The stars don’t align like this too often.

Adam Freeman is the former producer of MTV’s 120 Minutes, Alternative Nation, and Total Request Live. He is now the Creative Director of Thinkfactory Media. He tweets at @mradamfreeman.