The Most Insanely Awkward ‘Tonight Show’ Interviews

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The Most Insanely Awkward ‘Tonight Show’ Interviews

Whether you love it or hate it, The Tonight Show has a rich television legacy that stretches back for decades. The show remains very popular just as much for the wild celebrity interviews as the “zany” antics of Jimmy Fallon.

However, sometimes the show was memorable for all the wrong reasons. This is especially true when those celebrity interviews went completely off the chain!

Just how weird did things get? Keep reading to discover the most insanely awkward Tonight Show interviews!

Donald Trump

Jimmy Fallon’s whole thing is being affable to almost any guest, even when they are very controversial. But that really blew up in his face when he interviewed Donald Trump back in 2016.

This was when Trump was on the campaign trail for president and hoping to bolster his image. Toward the end of the interview, Fallon playfully mussed Trump’s hair to illustrate that it was real and not a hairpiece.

For many of Fallon’s fans, Trump was already deeply unpopular, so the late-night host ended up losing over 20% of his viewers. He ended up apologizing, but as Trump became president and performed one controversial act after another, many of Fallon’s former fans never forgave him for trying to normalize Donald Trump in this way.