Once upon a time, Howard Stern was known as a shock jock who would always make things as inappropriate and uncomfortable as possible, but he’s mellowed out considerably in recent years. In fact, he often gets guests to open up in ways they never would on other talk shows, but he has still managed to have his fair share of truly awkward and inappropriate interviews.

From the time Stern and Donald Trump both made sexual comments about Trump’s eldest daughter to the extremely awkward encounters Stern has had with David Arquette over the years, here are some Howard Stern interviews that left us feeling icky.

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Donald Trump | 0:00
Emily Blunt | 1:12
Gilda Radner | 1:50
Emma Bunton | 3:00
David Arquette | 3:46

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