But if there is a comic who's time spent in jail is probably the most historically impactful, it'd be none other than St. Louis' own, Dick Gregory. From May of 1963 to May of 1964, Gregory was arrested eight times, spending a total of two months incarcerated. However, his time behind bars had less to do with what he was saying on stage and more to do with what he was saying in the streets -- give Black America the same basic civil rights given to White America.

This week's album is Dick Gregory's premier special In Living Black & White. Here is the tale of the tape:

Recorded : 1961

: 1961 Venue : The Playboy Club - Chicago, Illinois

: The Playboy Club - Chicago, Illinois Label: Rhino Entertainment Company

1961 was a very different time. I think we, as a country, have an insanely short memory when it comes to the crazy shit we've done. 1961 was only 56 years ago. That's not even retirement age. That means that the older black dude you work with was born as a genuine 2nd class citizen. Institutionalized racism wasn't something hidden in complicated laws back then. It was right there in your face. White people can do this, and black people have to do this.

Joe, we know all this. And quite frankly, we don't ever like to be reminded about it. What does this have to do with a comedy album?

In Living Black & White was the first album of Dick Gregory's. He was 28 years old and had just opened the door for every successful black comic to come after him because he was a black comedian who had just started making good money performing in clubs full of white people.

Before this, the only black performers paid to do their acts in white clubs were the best singers and dancers. Black comedians weren't able to break out of the Chitlin Circuit - a national network of clubs, theaters, and other venues in which black entertainers were allowed to perform.

But this all changed one fateful night, when the boob-man himself - Hugh Hefner - stopped into the black-owned Roberts Show Bar in Chicago and saw Dick Gregory standing on stage and telling hilarious jokes about being a black man in white America. No other black comics had really addressed the civil rights struggle directly. Hefner ran The Playboy Club franchise and it was the most significant circuit for stand up comics in the 1960s - It's what gave George Carlin a national platform and made stand up comedy a viable living for many.

Gregory got the call to come work The Playboy Club in Chicago on January 13, 1961, and the story is pretty incredible, as he puts it in Kliph Nesteroff's The Comedians:

"They called my agent. He said, 'It pays fifty dollars for one night.' I couldn't believe there was that much money in the world. I had never been in downtown Chicago and I didn't have but a quarter. I got on the bus. I got off at the wrong stop. There was a blizzard that night. I'm supposed to be onstage at eight o'clock. I'm running and I'm slipping and I don't know where I'm going. The blizzard was so heavy you couldn't see -- and then I saw PLAYBOY and that was like seeing heaven."

As it turns out, while Gregory was trying his hardest to get to the gig, his phone was ringing at home because the club was packed with a convention of white businessmen from the Deep South. Playboy had decided to cancel his show and pay him off rather than inflaming a racial situation. Dick Gregory never got the message and he killed. He continues in the interview:

"Twelve o'clock I was still talking. Twelve-thirty Hugh Hefner came by. Two o'clock I was finished. From that they hired me for two hundred and fifty a week, seven days a week."

[I just want to point out here that I'm pulling this whole anecdote from Kliph Nesteroff's The Comedians. It's a fantastic book and I highly recommend it.]

Gregory instantly became a national headliner. Suddenly he was getting called for interviews in major publications and getting booked everywhere in the country. He had been the perfect voice at the perfect time. With the fight for civil rights just coming to a boiling point in the 60s, white America was ready to hear a black comedian's take on living in racist America.

Now before we talk about what came of his career shortly after, let's talk about this album. I couldn't find much writing on the creation of In Living Black & White, but it was recorded in The Playboy Club the year that Dick Gregory blew up. So it was the most fresh material of his breakthrough. Let me first start off by saying that the material is hilarious. Truly. Sometimes with these old comedy albums, you have to listen to them with an ear for the time because a lot of the old material is just too predictable in this time and age.

But Gregory is so cool and calm with his cadence while popping out funny anecdotes through his act. And his jokes are thoughtful and deep - even if they're just goofy. In fact, even with his more racial material, he never lets himself get too emotional with his delivery. White America wasn't going to listen to that just yet. He had to ju-jitsu his message into these jokes. He's mentioned in numerous interviews that he had to "learn the White man's jokes." In his 1964 memoir, Nigger, he writes:

“I bought white man’s joke books to figure out what whitey was laughing at — you know, mother-in-law jokes and Khrushchev. Then I made a mixture — twenty percent black, eighty percent white.”

By doing this, he was able to talk about racial problems in America without angering the people that could take his voice away. He was making fun of the institutionalized problems, not by aggressively making fun of white America, but by getting white America to make fun of themselves. And you hear it on the album.

But there is still that cringey white supremacy of the time stamped on the album. The entire album is presented by a broadcaster by the name of Alex Drier. The back cover is a presentation written by Mr. Drier as a way to introduce the world to Dick Gregory. He talks about Gregory in a way to reassure whites that this is not "negro humor" or "shock humor that will jar you or shake you up."

From what I could find of Alex Drier, he seemed like a man of principle for the time. He was known as Chicago's "Man on the Go" for his news reports all over the world on Chicago's ABC affiliate station. That was, until 1964, when he did a piece on air that criticized white neighborhoods that discriminated against black families wanting to move in. After that, he was driven out of town. He moved to Los Angeles and went on to have a somewhat decent career as an actor.