Episode 499 – BB King Live in Cook County Jail – Ryan Sickler


Episode Summary:

Songs of heartbreak and loss abound in this episode of The 500, which centers around B.B. King’s album Live in Cook County Jail, but this week’s guest doesn’t shy away from music that makes you want to cry into your beer or maybe even drive off a cliff.

Comedian Ryan Sickler has seen his fair share of hardship, and like the prisoners who were there to witness this album’s recording on the hottest day of 1971, he finds comfort in the shared misery these beautiful recordings extol.
In fact, Ryan has managed to turn some of the tragedies in his life into solid gold material that he’s been able to showcase on Viceland’s Party Legends, Comedy Central’s This is Not Happening, and his own storytelling podcast, The Crabfeast. Two of Baltimore’s favorite sons, Ryan and Josh have almost as much fun talking about who they’d love to see perform for a crowd of screaming felons as they do dissecting the fascinating minutiae of B.B. King’s life.
Sickler’s new album “Get a Hold of Yourself” is available for pre-order now on iTunes, Amazon & GooglePlay! It drops everywhere November 20, 2018, BUT if you pre-order now you get an instant download of one of his favorite tracks, “The Dad Whistle”.


Show Notes:

00:01:45 – Intro
00:06:45 – Episode starts
00:08:00 – The music Ryan listened to growing up
00:10:00 – Young Ryan’s dreams of starting a band
00:11:45 – Ryan loves the blues
00:13:15 – The blues is black people’s music
00:15:45 – Ryan’s first time hearing the album
00:17:45 – “The Thrill Is Gone” is a stand out hit
00:19:00 – Listening to the album as an adult vs. listening as a kid
00:21:00 – What Ryan likes about the blues
00:22:30 – Finding comfort in the suffering of others
00:24:45 – Being in a shitty jail would be the worst
00:25:30 – Smashmouth: Live from MoCo lock up
00:26:45 – The closest Ryan has come to going to jail
00:28:15 – The history of ‘Lucille’
00:30:00 – Ryan knows everything about B.B. King
00:32:45 – How Ryan met B.B. King’s kids
00:45:30 – The most famous person Ryan’s ever met
00:46:30 – How many times has Ryan seen B.B. King live?
00:49:00 – B.B. King knowledge brings free weed
00:50:45 – Listening to the album over time
00:56:45 – Exploring the lyrics of “How Blue Can You Get?”
01:00:00 – This album is a great introduction to B.B. King
01:03:15 – What parts are worth skipping?
01:06:00 – What influenced the album?
01:07:00 – Ryan’s Chuck Berry story
01:08:45 – Who did B.B. King influence?
01:10:30 – Does this album deserve to be among the 500?
01:13:00 – Comparing this album to others on the list
01:14:45 – Facts!
01:16:00 – Rolling Stone’s original review: not great
01:17:00 – Would you recommend this album to people?
01:18:15 – Snatch & Scriff!
01:20:30 – Outro


New Artist / Song influenced by BB King:

  • Benjamin Booker – “Witness” on (Youtube)


Guest Playlist:

Click here to check out what Ryan’s listening to today. (Youtube)



The 500 is a production of Native Creative Podcasts.

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3 thoughts on “499 – BB King Live in Cook County Jail – Ryan Sickler

  1. I saw BB at the Hollywood Bowl, Magic….. with the sun setting behind the stage.
    This adds to it. The man behind the music. Thanks for bringing it to life with amusing stories and very real life experiences. Entertaining 🙂

    1. Thanks for checking it out. The picture you paint at the hollywood bowl with the sunset backdrop sounds slightly better than Cook County Jail 😉

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