Celebrity interviewer and author Glenn Plaskin joins Greg for a light-hearted conversation. The pair discuss some of Plaskin’s favorite interviews–many of which turned into life-long friendships with his subjects. His goal, he says, was to get to know the people he sat across from–not trap them with “gotcha” journalism.

Plaskin is also known for his in-depth interview with Former President Donald Trump for Playboy magazine. The pair sat in conversation for 12 hours over several weeks. The result was an article that is still referenced to this day.