Howard Stern has earned a reputation as one of the most outspoken figures in radio history, with an envelope-pushing career spanning decades. Here are some of his most painfully uncomfortable interviews ever.
Before he was president, Donald Trump was a frequent guest on Howard Stern’s radio show in the 1990s and 2000s, and every interview contained at least one cringeworthy moment.
In September 2017, the Chicago Tribune unearthed a 1997 clip in which Trump said he could have, quote, “nailed” Princess Diana. At the time he made those comments, Princess Diana had recently died in a car accident.
In October 2016, CNN Money pulled together something of a highlight reel of Trump’s interviews with Stern, including a 2004 segment in which Trump agreed with Stern about his daughter Ivanka’s level of attractiveness.
Watch the video for more Howard Stern interviews that left us feeling icky.
#HowardStern #HowardSternShow
Donald Trump | 0:13
Emily Blunt | 1:12
Gilda Radner | 1:50
Emma Bunton | 3:00
David Arquette | 3:46
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