Deon Cole sits down with Shannon Sharpe at Club Shay Shay for a wide-ranging conversation full of wild stories and celebrity encounters. Deon kicks things off by asking Shannon if his infamous Instagram Live video was staged, setting the tone for the comedic and candid interview that follows.

Deon dives into his career highlights, starting with his latest Netflix special and the unforgettable moment when Paul McCartney attended one of his shows and even joined him on stage. Things took a crazy turn when Deon smoked a joint with Paul, which led to what he describes as the worst performance of his comedy career. Deon goes on to share other star-studded experiences of appreciation for his comedy, from visiting the White House and meeting Christian Bale, to encounters with Meryl Streep and Eddie Murphy.

In one of the episode's wildest stories, Deon recalls the time a man rushed the stage during one of his performances and swung at him, only for Deon to punch him back with the microphone still in his hand. Deon lightens the mood by talking about his experiences with weed, hilariously breaking down the difference between smoking with White people and Black people. He even shares how he was once such a terrible drug dealer that he ended up painting a house to settle a debt and how a prostitute gave him money for his first comedy headshots.

Deon reveals why he quit smoking weed for 13 years and reflects on conspiracy theories, police brutality, and his proposed solution for societal issues. He also opens up about masking personal pain with humor, dedicating a special to his late mother in Brooklyn on the one-year anniversary of her passing.

When the conversation turns to dating, Deon doesn’t hold back. He describes the dating scene as a mess, admits that he wouldn’t leave a woman who cheated on him, and hilariously claims all the baddest women are found in health food stores. He uses Halle Berry as an example of how difficult it can be to date someone incredibly famous, and shares his thoughts on the importance of a partner bringing peace rather than money.

Deon gets real about his celebrity dating experiences, including a time when Stevie Wonder stole his girl and made him take a cab home while she stayed with Stevie. Deon jokes that even President Obama knows about Stevie Wonder's reputation for stealing women. He also recalls dating one of Shaquille O'Neal's exes and admits he felt traumatized trying to "fill Shaq’s shoes."

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